A Quick History of Toronto’s Notorious Stanley Street

In the annals of Toronto history, Stanley Street is very possibly its most notorious street ever. It was so ill-reputed that its modern incarnation bears no resemblance in look, character, and name to the past. Indeed, Stanley was not even the first name of the thoroughfare, and it was not the last either; it started as March Street and ended as Lombard Street. Its route ran a very insignificant half kilometre between Victoria and Nelson (now Jarvis) Streets. It is this lack of distinction in geography married with its very important social dynamics and multiple name changes that comprise Stanley Street’s story.

The road that became Stanley Street has existed for roughly two centuries, and its infamy began early in its life. Kristine Morris, a leading historian of the street in all its versions and layers, noted that March Street’s ill reputation as a ‘red-light district’ was present as early as the 1820s and 1830s. Another great departing point for the poor state of the street was indicated in an 1849 “General Report of the Cholera in Toronto” by the Board of Health:

“March Street (as you are well aware) is for the most part, composed of low, undrained, ill-ventilated wooden building, chiefly occupied by the poorest classes of society to be found in this City, and taking into consideration the habits of many of its people, and the crowded and filthy state in which many of them live, it is a matter of no surprise that more than double the number fell victims to the Cholera there than in any other portion of the City.”

The Globe, October 20, 1849

There was also March Street’s very notable and negative association with Toronto’s Irish population. William Jenkins, a leading scholar of the Irish in Toronto, in describing the street’s demographic associations, wrote that the 1846 directory revealed that at least a quarter of the denizens of March Street were of Irish Catholic origin. This percentage would increase with time, reaching fifty percent and eighty percent. March was one of two major Irish Catholic enclaves along with Dummer (later named William and even later, St. Patrick Street). The Globe later recounted a myth it even labeled as ‘slander’ that the 1876 Police Station on nearby Court Street was so positioned because of the Irish on the street. Reports about the Irish Catholic contingent on the street were not particularly favourable in newspapers. As Jenkins has noted, The Globe “was ever vigilant in its crusade to improve the city by ridding it of immoral elements”. The bias against Irish Catholic Torontonians repeatedly came into focus on Stanley Street.

March to Stanley

It was this poor reputation that led to the renaming of March Street to Stanley Street by order of Former City of Toronto By-Law 153 on April 22, 1850. Its namesake was Lord Edward-Smith Stanley, the Colonial Minister and Prime Minister of Britain; his son also later lent his name to the Stanley Cup of hockey.

However, the prestige of the new name did not eliminate the stigma. It is a telling introduction to Stanley Street that in 1851, there were three taverns and twelve beer-houses on the street. It contained by far the most alcohol establishments in St. James’ Ward, tied only with busy Yonge Street. (A later report in The Globe in 1859 outlined a change to the licensing system which had taverns installed based on the recommendation of the area’s ratepayers; the writer suggested that Stanley Street would have a tavern in every other house in such a system.) The decade to come was filled with tales of drunkenness, death, assault, rows, robbery, fire, disease, murder, houses of bad repute, and more. And this was all contained in two city blocks.

The year 1854 was eventful with a range of interesting occurrences that demonstrated Stanley Street’s debauchery. In February, the body of Elizabeth Stanton was discovered in a stable behind the Forest Traveller’s Inn. Although an inquest was made, no wrongdoing was found. The death was ruled to have been “from the effects of cold and intemperance.” In another event in June, Police broke up “a general row” on Stanley Street while looking for four men, including “an idiot named Charley”:

“…The house was full of men and women in a beastly drunken state; the idiot, Charley had bitten a women’s leg and arm; the inmates were fighting upstairs, down stairs, in the beds, and in every place and corner they could find footing; blackened eyes were numerous and the unfortunate idiot’s face was covered with blood.”

The Globe, June 1^st, 1854

When Police arrived, the individuals who were not too inebriated scurried away while others hid under beds. The four prisoners were arrested, and they had trouble staying in the cart on the way to the gaol. In July, the Mayor and other city officials visited Stanley Street to find another shocking scene. There was a house containing many stolen goods: iron, brass, lead, pins, needles, coats, shawls, axes, and more. Next, in October, two women, Bridget Judge and Catherine Slattery, were taken in by police for disorderliness. Bridget’s eye was discoloured, and both girls “were well versed in Billingsgate oratory” – that is, vulgar language. Bridget was found drunk near a tavern at Church and Stanley Streets. She reportedly began to argue with herself and “pummeled a fence most lustily.” They later found her tearing another woman’s hair out. Finally, in November, a fire swept through a tavern on the north side of Stanley Street near Nelson (Jarvis) Street. It was terrifying sight; the fire could have ravaged the crowded quarters of the street if not for the quick action of firefighters.

There were further cases and examples of Stanley Street’s unfortunates in the coming years. In April 1855, a Duncan Fraser, 30 years old, was found in a garret “in a sad state of intoxication.” First, he was taken to the gaol, but as his health was suffering, he was taken to the General Hospital. There, he died. Anne McGrath, in December 1856, accused her neighbours and tenants, George and Mary Monk of assaulting her. The two women, Anne and Mary, got into an argument where each lady pulled the hair out of the other. The husbands were involved, and they too began to fight. It was such a bizarre situation that event the Police Magistrate of the Police Court, George Gurnett, found it difficult to sort through the facts that he dismissed the case outright. There was yet another quarrel the following month, this time between marital partners, in which Martin McGlenn struck his wife, Sarah, and then pursued her when she ran. She escaped into a neighbouring house, and in a fury, Martin threw a large stone in the window. He was fined for his angry outburst. Another family affair occurred in June when the Flynn family were all arrested for stealing goods. The children, Terence and Mary, 10 and 11 respectively, stole some boots and other items from John Bacon’s shop on Yonge Street. They were found in the family home on Stanley Street. The kids were committed to trial for larceny and the father for receiving stolen property.

The Orange Riot of 1857

A high – or more aptly, low – point of Stanley Street’s dysfunction came on July 12, 1857, when Irish Catholic and Protestant tensions led to a violent riot. A man named Devlin, an off-duty policeman, passed through the street at the corner of Church and Stanley. He was wearing an orange rosette – the emblem of the Orange Order (July 12 is Orangeman’s Day). Some observing Catholics took offense and ripped it off, spurring a crowd to gather and brawl to form between Catholics and Protestants. Police sped to the scene and broke up the riot, arresting eight or ten of them. They also stayed on scene to discourage another melee. However, after they left, another brawl broke out that night. Police returned and spent until four in the morning keeping the peace. For Devlin, the man who arguably started the provocation with his presence on the street, his arm was broken, and his face cut. Another constable, Ormsby, hurt his shoulder, helping Devlin. Six of the men that were arrested were let go with a large bail; the others went to jail to await trial.

At Police Court, the rioters were identified as William Corbett, William Kavanagh, Michael McMahon, Bartholomew Kearnes, James Kavanagh, Michael McMahon, Patrick Enwright, Michael Sullivan, Matthew Mahon, and Simon Cantwell and were brought on the charge of assaulting Constables Devlin and Ormsby. Constable Devlin did not appear in Court as he was seemingly tending to his injuries. A witness, Frederick Smith of James Street, deposed that he saw a crowd gathered on Stanley Street where they were bothering a Police Constable. Constable Ormsby then gave his deposition: he proceeded to the scene of the riot where he saw Constable Church with a prisoner. He took the prisoner and escorted him to City Hall and then returned to the street. There, he got into a brawl with Michael Kavanagh, who attacked him with a stone. Another witness, Orangeman William Mulholland, came in to help and heard some the Catholic men call out “to take hold of the d—d Orange b—r” and then tried to take his own Orange lily. He saw Constable Devlin emerge from a house bloodied. Another witness, John W. James identified Michael McMahon as “more violent than the rest”. McMahon lunged at another man and called “give me hold of the Orange “b—r”. He described a scene where stones were pelted at Police until the Constables got control of the scene and arrested the prisoners. With Devlin not able to be deposed, the prisoners were kept.

The next day, Police Court continued investigating the “disgraceful riot” by charging John Foley, who denied being involved. On the third day, the Mayor and Alderman O’Donoheo presided over the Court. More testimonies were heard, and a judgment was made. Michael Cavanagh, James Sulivan, Michael McMahon, Bartholemew Kearns, William Cavanagh, William Corbett, John Foley, and Michael Horan were committed to trial. The end to the violent July events were concluded at Recorder’s Court in November, when William and Michael Cavanagh, Michael McMahon, and Bartholomew Kearns were convicted of rioting.

Fighting and rioting was common on the street as in August of the year, several young men were brought up for the “desecration of the quiet and sacredness of a Sabbath morning” on the “already distinguished street”. Naturally, they were at a tavern acting disorderly. They were having a rowdy time; a fiddle was playing, and they were dancing, drinking, and making noise. Police arrived to cease the party, but they were ignored. A fight broke out, and arrests were made. It also so happened that the tavern owner, Carey, was not licensed. He was not happy with the charge and threatened to “smash” the constables. All the parties involved in the riot were fined 20s, and Carey for his threats was to give security to keep the peace for six months.

In November 1858, Michael and Anne Plunkett, brother- and sister-in-law, were charged with running a disorderly house. Brothels were common on the street. Anne adamantly denied the accusation. It was said “she took a drop of drink now and then, but she defied anyone present to say they had ever seen her act in a disorderly manner. Mr. Gurnett warned her, to a round of laughs, “Then you have been a much maligned woman, for I have hard quite a large number of persons swear you were a bad woman.” Michael Plunket was sentenced to find bail to keep the peace, and she was let go because the gaol was overly crowded.

The Brook’s Bush Gang on Stanley Street

Stanley Street was also frequented by members of the notorious Brook’s Bush Gang. The ill-reputed group had their headquarters in a wooded area east of the Don River, but they also had their haunts in the city. The disorderly group terrorized Toronto in the latter half of the 1850s and early 1860s, so their association with shady Stanley was fitting. One Brook’s Bush denizen who made his presence known on Stanley Street was John W. Clyde. He was often violent, drunken, and disorderly. In fact, Clyde’s first appearance in Toronto’s Police Court was in June 1856 when he was noted as “a notorious character”—a description that appeared in several reports of him—and was arrested in a ‘low house’ on Stanley Street. He was fined 25c and costs and sent to gaol in default of paying. To add, he was drunk and assaulted the officer when he was apprehended. In July, Clyde was involved in the murder of a young Black man, Isaiah Sewell, in the bush. He did not commit the awful deed himself – actually, none of the gang members were directly implicated and punished – but the affair shed a dark light onto Clyde and the group as whole. In November of the year, Clyde brutally assaulted an “old man” named John Douglas on Stanley. He was fined 50s and costs and, in default, was sent to break stones.

Beyond Clyde’s attendance, Stanley Street was familiar to other inhabitants of Brook’s Bush. In October 1858, Mary Ann Pickley was amongst “a depraved lot” of females who were found in a house on Stanley – known as “a notorious den of iniquity” in which an infant was previously smothered. They were committed to gaol for a month. In December 1859, Mary Sheppard of the gang was found by police frozen to death on Sayer Street, where she was attending a dance. Police figured she was going to Stanley Street, which was noted as one of the ‘haunts’ of the group. The same month, Maurice Malone and Cornelius Leary stole the watch of John Ault on Stanley. Leary again found himself in trouble on Stanley Street in August 1860, this time on the receiving end, when Anne Reordan assaulted him with a potato masher. In April 1861, Ellen McGillick — one of the primary characters in the late history of the group — was found in a house on Stanley Street by Detective Colgan. McGillick was present during the murder of politician and newspaper publisher of John Sheridan Hogan in December 1859. McGillick was solicited by the detective to inform on the group; her testimony as a witness would be key in the subsequent trials in the murder.

The decade of the 1860s served no better to ease opinions of Stanley Street. In April 1860, two well known “rowdies” got into a fight after consuming a lot of “bad whiskey” in a low tavern on Stanley Street. The melee spilled onto the street where a crowd gathered. A constable went to stop the fight, but he too was pummeled. Another officer in the vicinity went to help and carried the rowdy men to City Hall Station. In June 1865, “three blossoms of iniquity from Stanley Street were arrested for disturbing the peace and quiet of the street “to an inordinate extent. The Globe noted Sundays were generally light work for the police but this trio thought they would be causing no harm. In December of the same year, a man named Wellesly Coats, entering a store on Church Street near Stanley Street, left his horse and wagon in front of the place. He placed a rug on the horse. When he emerged from the shop, the covering was gone. The assailants were Elizabeth Cadwell and Ann Finelly, aged 12, “both denizens of the notorious Stanley Street.”

A Cesspool of Disease

In an episode akin to the cholera report some seventeen years prior, the middle of the decade very much brought out its poor state of health again. In the February 14, 1866 edition of The Globe, a full-page report was published entitled “Sanitary – Slums and Filth of the City – Public Health in Danger – Prompt Measures Required.” While the expose included many areas of Toronto, Stanley Street’s inadequate conditions featured heavily:

“Take that plague-spot of filth and misery, that cesspool of disease – Stanley street – and look at its back yards and closets, and you have but a sample of what can be seen in filthy other plague spots in the city.”

The Globe, February 14, 1866

The Globe took a tour of the street, highlighting first the rear areas of residences which were, in the newspaper’s observation, more fitting for animals than people. From Victoria to Nelson Street, there were at least 28 closets (ie. outdoor toilets) in a disgusting state “that it is hard to comprehend how any man, however low and degraded a social position, could eat, drink, and sleep within gun-shot of them.” The pig pens were also a health nuisance. Entering a house, the report noted how at least ten people were huddled in a room 12 x 14. The stove was red as the mid-day food was being prepared, a woman was cleaning linens, the walls were black, and the stench of the pig pen travelled into the home. In another home close to Nelson on the south side of Stanley street, the newspaper was in disbelief that another room used for all cooking, eating, and sleeping could be beside animals’ pens.

The Globe’s harsh depiction of Stanley Street was followed with a lighter take in March 1867. It reported that “Stanley Street has been exceedingly turbulent during the past few days.” Its tone was seemingly ironic in noting how “its prestige [was] on the wane” and labelling the street as a “happy spot.” The events included a row between females caused by a drunk man attempted to enter their homes, the sight of an ‘amazon’ welding a cleaver, a melee between two men and two women, and most interesting, a brawl between a ‘devoted wife’ and another woman who had captured the attention of the first woman’s husband.

The newspaper published yet another awful account of the street in December 1868 when a reporter documented his experiences on the street on Christmas Eve. It started with his interactions with a poor girl selling newspapers. Pitying her, he bought all of items and then accompanied her to her house on Stanley. There, he witnessed a domestic disturbance with the girl’s parents. The reporter continued to tour the street and its dwellings, painting a grim picture of its poor denizens:

“Over and over again we came across old women, who were rather comfortably situated, yet had no apparent means of making a livelihood of any kind. When questioned on this point some refused to give any reply; others prevaricated in the most transparent fashion; while others the reply was they kept lodgers who were all out.”

The Globe and Mail, “How Christmas was spent on Stanley Street”, December 18, 1867

The ‘Mayors’ of Stanley Street

If Stanley Street was a stage with these very dramatic performances, it fittingly had its own cast of characters. This was highlighted by its very own ‘mayor’: James Doyle. In the Robertson & Cook’s Toronto city directory for 1870, Doyle was listed as labourer living at 39 Stanley Street. In the 1871 Census, he was identified as an Irish Catholic. He had some colourful tales attached to his name. In March 1869, Doyle was accused of “once more” poking out the eye of Jerry Shehan, a labourer at 47 Stanley. In this latest occasion, the two men had a run-in while drinking at a bar. When Shehan left, the Mayor followed him and proceeded to assault him. Prior to this violent engagement, Sheehan and Doyle are also noted as assaulting each other in February 1865 and again November 1868, so they were very well known to each other. This opposition relationship was confirmed by Doyle in October 1870 when Sheehan was on trial for stealing a purse and Doyle deposed that he and Sheehan “were not on friendly terms.”

Doyle may have had enemies as another event in June had the Mayor’s home burglarized. Mrs. Doyle deposed that she woke to find a back window open, and her ‘bureau’ had been carried to the backyard, broken, and robbed of its contents. A gold chain, two silver watches, two shawls, a black jacket, two silk aprons, a pair of cuffs, and $34 in cash were gone. James Leary and Pat Kavannagh were arrested. In July 1870, Mayor Doyle was fined $20 or given one month in gaol for assaulting Frank Conlin on Church Street. Finally, Doyle was a witness in the trial of Robert Wagstaff for the murder of Margaret Chapman. Wagstaff belonged to the Brook’s Bush Gang. Wagstaff and Chapman were drinking at Doyle’s house on Stanley Street on the night Chapman drowned.

The ‘office’ of the Mayor of Stanley had a successor in Daniel Dwan. Like Doyle, Dwan had his own misadventures. In 1878, it is reported that Dwan had a rivalrous relationship with a shoemaker named Michael O’Connell. There was one runin on Jarvis Street with Dwan wielding a stone and O’Connell a knife. In another fight, the shoemaker apparently badly assaulted the mayor, but the charge was dropped based on little evidence. In 1878, Dwan is listed as a labourer living at 85 Lombard (along with John Maley and George Maley). Dwan also had a wife named Bridget. After Daniel’s death, in 1883, Mrs Dwan was taken by Police “as a vagrant, having been wandering about the street in a destitute condition.”

A Final Name Change

In 1876, a breaking point seemed to have been reached concerning Stanley Street’s seedy character. In March, Alderman Wright introduced a bill to the City Council to change the name. “[Wright] explained that many respectable people would settle on the street, were it not for its name, which was associated with everything odious.” Then, on November 27, 1876, by order of By-law 764 “To Change The Names of Certain Streets In The City of Toronto”, as it had 26 years prior, the street received a new moniker: Lombard Street. There was a prestigious street of the same name in the centre of London housing the city’s financial heart. Hopefully, the association could rub off on the Toronto street. The Globe, however, was skeptical that a new name would make a street “smell a good deal sweeter”:

“The same cure was tried once before in the case of Stanley-street when its name was changed from March Street, with what success we all know. Nor are the same tactics likely to prove any more effective now. It is plain to every observer that Stanley-street has already begun to amend, and the rapidity of its progress will depend, not on the change of name to Lombard-street, but on the speed of which its present tenants and their rickety tenements disappear, and a better class of each take their place.”

The Globe, “Street Nomenclature”, December 7, 1876.

Indeed, The Globe continued to report on Lombard Street’s vices and the pointlessness of the renaming. In 1882, it derisively mentioned that a more appropriate new name would have been “Whiskey Avenue.” It questioned the existence of the slummy street in the middle of “the Queen City of the West” and labeled its denizens “of the lowest classes in the community.” In 1888, the newspaper reported again on “The Horrors of a Lombard Street Tenement. ” Although the article was yet another gloomy portrayal of the street, it did contain a hint of positivity: parts of the street were improving! In the next year, The Globe wrote:

“The name of Lombard is not unknown in the Police Court either, but still the street is improving – not, it is feared, because the residents have improved but because the old rookeries are being pulled down and their place is being taken by good business buildings.”

The Globe, January 14, 1889

By the end of the century, Lombard Street had a distinct identity than Stanley Street. Its rowdy denizens were just about gone. The old, shoddy buildings were razed, and factories and warehouses took their place. As Kristine Morris wrote: “Progress took care of what street name changes could not.” A look about the street today is jarring as there is no indication of what was once Toronto’s most notorious street.

Cover image: Fleming Topographical Plan of the City of Toronto, 1851. Credit: Old Toronto Maps

Acknowledgments: This article builds upon the work of William Jenkins, Kristine Morris, and Katherine Taylor. Each has produced insightful histories of Stanley Street. Thank you also to Francesca Bouaoun of Toronto Archives for the aid in locating by-law 153.

Toronto’s ‘Skating Mania’: Ice Rinks in the 1860s

“The skating mania has reached Toronto, and the entire population have taken the disease in the most virulent forms.” This was The Globe’s declaration in the February 12, 1862 edition of the newspaper. It launched a flurry of activity and new ventures that thrilled Torontonians.

Torontonians were already engaging in the frozen activity in the decades prior to the newspaper’s affirmation. In 1835, John Howard produced watercolour paintings of people skating on Toronto Bay near the wharves. There were also ponds at the foot of Windsor Street, near the Northern Railway Station at Bay Street, and at the feet of Peter and John Streets. The Globe in early 1862 spoke of an “accidental” rink on The Esplanade. The pond had “a great advantage over many others for skating, as in the event of the ice breaking, the water is only a few inches deep.” It attracted many people, including a large number of young ladies, who went unfazed with laughter as they fell on the ice.

But the actual purpose of The Globe’s February 1862 article was to declare that a permanent and purpose-built skating rink was “A Public Necessity.” Toronto Bay was a “splendid skating ground,” but the ice was unreliable. Indeed, there were several past reports of drownings. As for The Esplanade, despite the less perilous ice, the area itself was too small. A dedicated locale was needed for the wintery pastime. The newspaper recommended a spacious place, not susceptible to the wind, and that could be supplied with water. It proposed the University Park on the banks of the creek running through it. Some days later, a reader from Lower Canada — Skates — chimed in in agreement of the University Creek scheme. Montreal already had a skating rink since 1859 with a $5 subscription model.

The issue resumed again in the autumn — with much progress. The Toronto Curling Club, its president John O. Howard, applied to Toronto City Council to build a structure that would be used for curling and skating in the winter months. In a City Council Meeting on October 21, 1862, the City Corporation approved this intention “to construct a large skating rink for the recreation of the citizens.”

On October 29, the newspaper reported that a 300 by 150 feet rink was under construction. Somewhat confusedly, this was not the rink referenced by the Toronto Curling Club. This was the Victoria Skating Rink according to an advertisement on the same day. The ice was to be eight inches thick — which The Globe oddly noted was sure enough to accommodate a “large man” — of which there were a few in Toronto. The rink was going to be located on the south side of Gerrard Street at Pembroke Street, opposite the entrance to the Horticultural Gardens. The Honourable George William Allan, M.L.C. — who also donated the land for the Gardens — provided the land. It was to be surrounded by a six foot fence and would be lit by gas and illuminated at night. A house with apartments was to be built too. The cost to build the rink was $800. Advertisements for the Victoria Skating Rink would soon go out, enticing would-be members to come to the office of Treasurer R.J. Kimball at 10 Toronto Street.

As for the Toronto Curling Club, it started on its venture on The Esplanade near the Customs House. The Toronto Skating Rink would have 300 square feet for a skating pond, be lit with gas (like the Victoria Rink), and have “comfortable dressing rooms, with attendance and every comfort for skaters.” Tickets would go on sale at the office of James Fraser at 5 King Street West. Single season tickets were $2 and Family tickets were $5. As it held its annual general meeting in early November, workers prepared the premises — leveling the ground and constructing fences.

To add to the mix, in the advertisements of The Globe on November 11, 1862, the Riley, May & Co. announced the construction of a third rink: The West End Skating Park. It was placed under an ad for the Toronto Skating Rink. It was to be located at King and John Streets. Subscribers could sign up at the Revere House.

The Victoria Skating Rink and The Toronto Skating Rink opened around the same time — possibly even a day apart. The Victoria Skating Rink, which served residents in the northeast part of the city, was operational by at least December 9. Ads noted in the last days of November that it would “be ready to use as soon as there was ice.” The entrance was off Sherbourne Street and there were heated rooms for men and women. There was no alcohol to be sold. The Toronto Skating Rink opened at a central locale in the city at the south side of Front between Yonge and Bay by at least December 10. The event was marked by a Grand Skating Carnival. It was a brilliant and picturesque scene with hundreds in attendance. There were many falls but none were hurt.

Meanwhile, Riley & May were working at readying the West End Skating Rink. It was being flooded with water by the Water Works Company and the owners “had fitted up everything comfortably for their subscribers.” They expected to put up a flag at the Revere House — a hotel also under their management — to signify that the ice was good. By December 23, the rink was operational and lit up for the first time “with fine effect.”

On February 28, 1863, the Victoria Skating Rink hosted a “Grand Skating Match”. The prize was a silver flower stand to the best lady skater. At least one thousand ladies and gentlemen attended. A band played at the entrance. Ice conditions were not good due to the sun. The first prize went to Miss Allie Worts. These skating carnivals would become a fixture of the rinks for the years that followed. The Toronto Skating Rink held at least five gatherings in early 1863, including one on March 19th. The band of the 10th Battalion provided music and the building was “magnificently decorated and brilliantly lighted with gas.”

Women had a noted presence and active participation on the rinks. Even before the advent of purpose-built rinks, they skated on ponds in great numbers. In one scene at The Esplanade pond in January 1862, there were 50 women of a total 200 participants. One letter to The Globe from “The School Girls” however noted that they may not have been always welcomed. Even though they had “pretty well mastered the art of skating,” women had been banned from the Peter Street pond. When the dedicated rinks were built, the pastime was a family affair. Moreover, in addition to competing in carnivals and competition, there were ladies rooms and, in the case of the Victoria Rink, a female attendant to wait on female skaters. And they were vocal in part in the operation of the rinks. In 1864, “A Lady Skater” wrote against smoking at the Toronto Skating Rink. (Another reader — “A Ticket Holder and A Foreigner” — wrote it was disgraceful that a female had to appeal to a newspaper to stop the disgusting act.)

In May 1863, Orrin Wardell, the proprietor of the Victoria Skating Rink, was honoured at the City Baths. It was perhaps the first time the venue’s owner was named. (In January, a subscriber to the rink complained of the smoking at the rink and noted he did not know who owned or operated the establishment.) Wardell was presented with a silver plate and tea set. Wardell’s story is an interesting one. Not only was he not listed in the initial communications about the Victoria Skating Rink, he was listed as a house mover in the 1862-1863 Hutchinson’s Toronto directory. He was living at 55 Centre Street. By the 1864 Directory, Wardell was listed as a house mover and proprietor of the Victoria Skating Rink and the City Baths at Maria Street (now Soho Street) and Phoebe Street. Wardell had relatives named Isaac and William that were also house movers. By the 1866 Directory, Wardell was listed as both a proprietor of the rink and a new career: auctioneer.

For the 1863-64 winter, there were exciting developments across the skating rink world. Hardware stores, which had regular ads in the newspaper promoting their goods, were “decked out with skates.” And there were improvements to the gear too: “…[Now], instead of some 15 or 20 minutes being wasted at the border of the ice in applying the skates, they can be put on in an instant, and removed in the same space of time.”

For the spaces themselves, Mr. Wardell had enlarged the Victoria Skating Rink to a size of “300 by 250 feet, thus giving ample room to the lovers of skating to glide around with comfort and easy.” Mr. Riley of the West End Skating Pond had improved on his rink, taking notes from visiting rinks in Montreal and in the Eastern United States. The ladies’ retiring room amongst other buildings had been enlarged. As for the Toronto Skating Rink, it too had undergone repairs and The Globe had never seen its ice in better condition. It was as “smooth as glass.” And finally, there was another rink: the Yorkville Skating Rink! The venture had begun the previous spring and was now by leased by Thomas Berney and George White, who had “enclosed a space of three hundred feet by two hundred and fifty feet, with a closed boarded-fence seven feet high. It was located off Yonge Street, opposite Isabella Street, to serve the people of Yorkville. With its addition, “citizens will have abundant opportunities to practice this exhilarating amusement during the present winter.”

In November 1864, a new rink — the fifth in the city — would come. The Royal Skating Rink would be located west of the 10th battalion drill-shed at 84 King Street between Bay and York Streets. Reid & Harris were the proprietors. It would contain two rinks — one covered and one opened.

At the start of the following year, it seems like at least some were growing weary with how the rinks were being operated. In fairness, there had been complaints about the conduct of patrons since 1862, including the mentioned complaints about smoking, but there were two noted unsatisfied guests in early 1865. In January, a reader wrote to The Globe to note the dangerous practice of little boys furiously chasing each other on the rink. The writer, his lady, and some friends had heavy falls because of such behaviour. He implored the managers to act and suggested quartering a portion of the rink for figure skating. In March, a Pater Familias wrote about the fun festivities of the rinks. Curiously, he declared that the “glory of the skating rinks had departed” because of festivals and competitions. The purity of the rinks had been corrupted. Earlier in the month, the Globe wrote about the Victoria Rink Masquerade. “Those who appeared in character played their parts well. Everybody, indeed, was delighted and came home satisfied.” Pater Familias implored the return of the rinks “to their healthy simplicity”.

Despite this, it seemed like the allure of the wintery activity was still strong. For the new campaign in December 1865, The Globe wrote: “skating, the most popular of out-door recreations, is now anticipated eagerly; preparations are making on all sides for a brilliant campaign.” It went on to outline the activities of main rinks — the Victoria, Toronto, and Royal Rinks — including their carnivals. Some bad news was offered, however: The West End Rink would not to be opening. (It would be “shut up” the following year too and there were no more references to it in The Globe.) In the following December, St. George’s Rink opened at Maria (Soho) and Phoebe Streets, near Wardell’s City Baths. It was later reported to be the “largest covered rink in the Dominion.”

Of course, makeshift ponds continued to be enjoyed. People glided between the wharfs and other areas of Toronto Bay as well the Don River. “The Don has already been bridged by a strong table of ice and skaters yesterday piled industriously over its frozen surface,” the newspaper declared on December 12, 1866.

For the start of the campaign in 1868, The Globe reported the opening of the St. George’s Rink and Toronto Skating Club was met with less enthusiasm as years prior. The Skating Club was hosting curling matches and one subscriber noted how rinks were made over the skating portion. The managers of the St. George’s Rink transformed the venue to accommodate a new pleasure: the bicycle. It opened the Velocipede Rink — a “MAMMOTH RINK” — in April 1869. The St. George’s Rink was planked and furnished with seats to host “the best and largest place for Velocipede exercise in the country.”

The last reference to the Victoria Skating Rink was in March 1868 advertising a Grand Masquerade at the Victoria Rink. The rink was not listed in the directory for that year. As for its proprietor, in the Robertson & Cook’s Toronto city directory for 1870, the following listing is given: “ORRIN WARDELL, Auction and Jobbing Mart, wholesale & retail dealer in general merchandize, watches, jewellery, corner of King Street East and East Market Square, house 32 Frederick Street.” In the listing for St. Lawrence Hall, one finds: “O. Wardell, wholesale jobber in glassware, fancy goods.” In an entry for his son, Fred Wardell, the Detroit Historical Society noted Orrin moved from Toronto to Detroit in 1874 to establish Wardell & Sons, auctioneers.

In the years that followed, Toronto would continue to skate — on new rinks, using new technologies, and even new pastimes like hockey that repurposed these winter spaces — but the frenzy of the early 1860s marked the true beginning of the city’s skating culture. What had once been a scattered activity on frozen ponds and along the Bay was, in a few short seasons, transformed into an organized, social, and commercial phenomenon that reshaped winter life in the city. The rinks of 1862 and beyond did more than provide recreation; they created a shared civic experience, one that blended leisure, innovation, and community. And while the glide of skates would carry Toronto forward into the decades ahead, it is here—in this moment of “skating mania”—that the city first found its footing on the ice.

When Toronto’s Coffee Went ‘Continental’

Note: This article first appeared in Spacing Magazine Issue 71. It has been reproduced here with permission.

When Toronto’s Coffee Went ‘Continental‘
By Bob Georgiou

Cover image: Jack & Jill Coffee Bar in ‘The Village’, Hayter Street and LaPlante Avenue, 1963. Source: City of Toronto Archives

In March 1955, The Globe and Mail reported a growing “Toronto Trend”: the coffee house. While the drink itself was already sold and consumed in Toronto in various establishments (one of which was created by the temperance movement in the last quarter of the 19^th century), in the middle of the 20^th century it adopted a European, Bohemian, and outdoor flair. The newspaper also identified the catalyst of the new craze as “an Italian device known as the ‘expresso machine’” that had already caused a resurgence in coffee consumption in Britain.

On April 22, 1955, the Concerto Coffee House opened at 89 Bloor Street West. It billed itself as “Toronto’s First Continental-style Coffee House.” It was launched by partners British Brigadier Claude Dewhurst and Hungarian Irving Bolgar.

That June, in her Globe and Mail column “Around The Town,” Mary Walpole wrote about the cafe’s success:

“…And now in Toronto, the Concerto Cafe has proved that what we wanted most was a place to relax with our coffee and our chatter where the atmosphere…the service and the food made you feel that silly it is to rush like mad and get nowhere. The only problem is that too many people want to relax at Concerto Cafe…they line up for lunch…they drop in by hundreds to talk over the theatre, the film and the concerts with one of the twelve famous brews of coffee…though it’s still the Espresso that most everyone orders…and to dally over the intriguing salads, the Danish smorgasbord and French hors d’oeuvres and those delicious ices and pastries.”

The Globe and Mail, June 15, 1955

Another article in The Globe and Mail described the cafe’s “unusual aspects” – specifically that it was located above street level and featured “long-legged stools at a serpentine counter” where patrons could people-watch. The restaurant displayed interesting design motifs by Hungarian-born ceramicist Maria Rahmer de Nagay and the artist Karl May. The cafe also had a second-floor space called the “Picture Room.”

The cafe’s coffee itself was a mix of South American, Central American, and South African beans. An assortment of cakes and pastries provided accompaniment. Main courses included Hungarian goulash, veal ragout, stuffed peppers, chicken Tetrazini, and lobster Meridon. Later reports suggested the Concerto increased its selection of coffees, with espresso notes as the highlight, from 12 to 25 types.

The cafe, which was self-described as “Continental Bohemian”, had a happening vibe, frequented by “stars and celebrities.” In May 1955, opera singer Zinka Milanov was hosted at a coffee party there by the Yugoslav Consult General. Another soprano, Licia Albanese, stopped by the cafe after her show at Massey Hall in December 1955. Folk singer Greg Curtis was brought in to perform at the club, and a ‘singing Troubadour’ was a regular showcase. The owners, seeing the early returns of the Concerto Cafe, soon opened a second restaurant, the Concertino, at 32 Avenue Road. It sought for a similar atmosphere, and Maria de Nagay also provided her work for this foray. The Concertino was sold by March 1956 and renamed La Coterie.

Despite its great impact on Toronto’s gastronomic scene, the Concerto had a relatively short life. On December 13, 1959, a devastating fire totaling $15,000 in damages forced the cafe to close forever. The ground floor partially collapsed, and two firemen were hurt. A cigarette butt in the basement was believed to be the cause.

Meanwhile, another cafe with European flavour was contributing to converting Toronto to the new coffee culture. In March 1956, the Gaggia House at 28 College Street opened with a lavish gala. The owner was Venetian-born Pino Riservato, who fashioned the restaurant with Italian artistic stylings and a wood-burning oven for ‘pizza pie.’

But the intrigue did not stop in the coffee house’s interior: Gaggia House was also to become a sidewalk cafe, one of the first — if not the first – of its kind in Toronto. The Gaggia House seems to have only lasted six months, according to the Toronto Daily Star. But the trend had been initiated. In July 1960, Mary Walpole reported on the new sidewalk cafe of the Chateau Briand at neighbouring 32 College Street. She described how the “Wondrous Italian, Viennese and French coffees taste just that much better in this [patio] setting.”

By the end of the 1950s, the coffee house trend had completely caught on in Toronto. The Toronto Daily Star declared an ‘espresso blitz’ was taking place. “The most tell-tale sign of espresso’s growing popularity is that it is now being drunk during the ubiquitous Canadian ‘coffee break.’” Since the middle of the decade, the “continental coffee habit” grew to thirty espresso-serving establishments in Toronto. Another that grew from Hungary’s famed café culture was the Domino Cafe at 255 College Street owned by Hungarian-born Louis (or Leslie) Fekete.

Further west on College, the Capriccio Restaurant and Billiard Hall at 580 College Street, run by brothers Dante, Claudio, and Vittorio Cocca, helped launch Toronto’s Little Italy neighbourhood as an epicentre of sidewalk cafes, with long-running establishments such as Café Diplomatico continuing the activity to this day.

In the 1960s, Toronto’s Bohemian, Continental, and accompanying coffee cultures settled into two other districts. The first was ‘The Village’, an area west of Bay along Gerrard, Elizabeth, and Hayter Streets. In March 1960, Estonian-born Peeter Seep opened a new coffee house at 23 Gerrard Street. The Jack and Jill Coffee Bar on Hayter Street, another Hungarian establishment, was a popular spot with a sidewalk cafe and “after-dark activity.” By the middle of the decade, the Village was known for its coffee houses, live music, and patios.

The second of these areas would become the most synonymous with coffee house culture in Toronto’s history. Interestingly, it was located in Yorkville, steps from the ill-fated Concerto Café. In 1963, the Star reported a sidewalk cafe “boom” in Toronto with sixteen patios in the city — many of them in the streets north of Bloor near Avenue Road. The newspaper described how, in 1960, the Half Beat on Cumberland Street was persuaded by a former sidewalk cafe restauranteur and espresso machine salesman to place some tables outside. Their clientele soon preferred to sit or stand in the open air to drink their coffee. More coffee houses followed, many of them European-owned and -operated: the Old York Lane Cafe, the Coffee Mill, the Roof at 137 Avenue Road, the Penny Farthing, the Das Uppenbrau, the Cumberland Cafe, and La Provencal. Yorkville’s coffee houses provided venues for folk, blues, and jazz artists – some who laid the groundwork for a Canadian popular music scene.

Redevelopment in the Village and Yorkville erased both districts as nexuses for coffee houses. Many of the former converted rowhouses that had hosted the cafes were demolished. Nonetheless, as of 2025 the location of the Concerto Cafe remains at 89 Bloor Street West. Although no physical marker exists yet, it’s a good reminder of where Toronto got its taste for coffee nearly 70 years ago.

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The City Pound on Eastern Avenue

Note: This article first appeared in The York Pioneer and Historical Society Journal 2022 Volume 117. It has been reproduced here with permission, with minor edits.

Cover image: Plan shewing the Survey of part of the Park East of the Town of York into 1/2 Acre Lots by Command of His Excellency Sir John Colborne, Lieutenant Governor &c By James G. Chewett Surveyor York June 21st 1830. Source: Ontario Ministry of Natural Resources, Office of the Surveyor General: SR394 [via Distillery Historic District]

For nearly a century, a pentagonal plot of land existed at the foot of Sumach Street on the east side of Toronto. Its odd shape was created by a bend in what is now Eastern Avenue to the north, Cherry Street at its western edge, and a smaller street framing its southern and eastern sides. This space went through multiple uses before disappearing altogether from Toronto’s street grid.

This uniquely shaped lot of about 12 acres was laid out by at least 1830. Before this, the area east of Parliament Street to the Don River was the “Park Reserve” — government land originally intended for ‘other’ uses. South Park Street, the old name for Eastern Avenue, takes its name from this historical locale. An 1830 Plan (see cover image) for the area earmarks its potential original use as “Reserved for a Market”. Few details exist about this history, but it must be noted that the smaller street along its south and east was originally named Market Street.

By the 1850s, the marketplace became “The Pound”. More specifically, it was the City Pound. The City Pound was a very important piece of civic infrastructure in mid-19th century Toronto. The area was reserved for stray animals, namely cattle, which had wandered off from their owners. The related governing law was “The Pound Law,” which outlined the powers and provisions for municipal pounds. It set out which parts of the city were subject to the law, how many pounds were required in the city, the powers of pound keepers, and more. It was amended many times in the 1850s and 1860s. For example, in June 1858, it was proposed: “it should not be lawful for any person to drive cattle to the Pound between the hours of seven o’clock in the evening and six in the morning.” This was to combat cows being taken out of stables during the night and brought to the Pound, which was much to the chagrin of ‘many respectable people’. In April 1863, it was moved that the fine for allowing pigs to roam on the streets be increased from sixty cents to one dollar. In 1876, an alderman motioned to convert the city pound to a cattle market. It was referred to the Committee on Public Markets, but nothing appears to have resulted from the proposal.

By 1880, South Park Street was renamed “Eastern Avenue”. The Eastern Avenue City Pound was relabeled the “East Pound” in the city directories. Curiously, two other entries were also present: at 75 Eastern Avenue: Lackey Jas, caretaker (City stables); and at 77 Eastern Avenue: Corporation Stables. The directories later in decade labelled the stables at 95 Eastern Avenue. An October 1886 Globe article mentioned police horses were “stabled in the city’s old building at the foot of Sumach Street.” Fire Insurance Maps from 1889 show that the plot was built on in the decade, including “city weigh scales.” Other maps from the time also show several buildings on the site at the time.

In 1888, Market Street was renamed Worts Avenue. The Gooderham and Worts Cooperage was located on the south side of the street, east of Cherry Street and north of Front Street. In 1901, George Gooderham built three semi-detached houses on the south side of Worts Avenue.

By the early 1890s, “The Pound” was made a public park. This park seemed to have several names in the records: St. Lawrence Square/Park (named for its ward), or Coatsworth Park, which is said to be the original name for the park. In June 1894, a large open-air meeting was held in the park for a Labor candidate in East Toronto. In the 1900s, the park hosted concerts from the Cadet Battalion Band, the Governor General’s Body Guard Band, and the Queen’s Own Band. Interestingly, by 1910, the city stables and city pound were moved further east on Eastern Avenue between Cypress Street and the Don River.

In March 1906, it was announced that the Canadian Northern Railway was looking at the eastern central district of Toronto as the site of their new freight shed to serve its James Bay Railway. The railway purchased a large property bounded by Beachall Street, Trinity Street, Front Street, and Eastern Avenue, which included St. Lawrence Square. The sale price of the park was $14,000. The move would have perhaps the most transformative effect on the space.

It does, however, look like St. Lawrence Square endured into the 1910s. The Toronto Playground Association opened the C.N.R. playground in the park in the summer of 1911. The city finally reported the closing and sale of Worts Avenue in 1917 to the Canadian Northern Railway (Canadian Northern merged with Canadian National Railway in 1923). The park no longer appeared in the directories by the end of the decade. In the 1920s, the Dominion Wheel and Foundries Co. occupied the site. With Worts Avenue gone, it spelled the end of the pentagonal plot that once housed the market, city pound, and corporation stables and yard.

In the 1960s, the complexion of the corner changed again, partly to accommodate the new Don Valley Parkway. Sumach Street was rerouted to curve and align with Cherry Street to the south. Eastern Avenue was rebuilt with a new alignment between Sumach and Lewis Street (located east of the river), curving northeast at the former location of St. Lawrence Square. It effectively removed the distinguishable northern corner of the former city pound. The move also closed the old Eastern Avenue Bridge over the Don River (the causeway still stands today, leading to nowhere).

In the late 1980s, as Toronto as a whole moved into a post-industrial era, the area south of Eastern Avenue and east of Cherry Street was earmarked for redevelopment. The industrial and railway lands were to be rezoned for residential use. The original name of the project was “St. Lawrence Square”, later renamed “Ataratiri”. It eventually failed. In the 21st century, the lands finally became the new Canary District development, part of the West Don Lands mixed-use community. The history and geography of the former market, pound, and park is now hidden under an eco-friendly self-storage facility.

The Evolution of Castle Frank Hill, Toronto

Note: This is the second article in a series which aims to describe the 230-year evolution of the Castle Frank area. The first part is available here.

“The Sugar Loaf hill stands alone in the Don Valley. It is still covered with woods that join with those of Castle Frank, a quarter of a mile off in the woods, between the two hills, is a pine-tree in whose top is a deserted hawk’s nest. Every Toronto school-boy knows the nest, and, excepting that I had once shot a black squirrel on its edge, no one had ever seen a sign of life about it. There it was year after year, ragged and old, and falling to pieces. Yet, strange to tell, in all that time it never did drop to pieces, like other old nests.”
E.T. Seton, Wild Animals I Have Known

In 1898, author, naturalist, and artist Ernest Thompson Seton released his famous Wild Animals I Have Known, a compilation of short stories from his time exploring Toronto’s wilderness in the 1880s and 90s. In particular, Seton spent a lot of time in the Don Valley and Castle Frank Hill. English-born Seton grew up in nearby Cabbagetown.

E.T. Seton’s tales recounted the stories of the certain wildlife inhabiting the district, including Silverspot the Crow, Red Redruff the Patridge. He also noted other animals such as the blue jay and rabbit. Prevalent in Seton’s characterization of the fauna of the area were the old pines, hemlocks, grapes, and berries, altogether painting a pristine picture of the hill.

Decades later, another Don Valley explorer, conservationist Charles Sauriol also recounted the hill:

“The visitor who glanced down from the ramp of the viaduct, sees the top of the hill almost level with the floor of the bridge. The C.N.R. line flanks the hill on the east. North-westwards, a panorama of woodland (Old Drumsnab), becomes in summer a vista of undulating waves of billowy leafage extending towards Rosedale Ravine.”
Charles Sauril, Tales of the Don

Sauriol spent his summers between the 1920s and the 1960s in a cottage in the Don Valley. He was an advocate for the preservation of the valley.

The Castle Frank that Seton knew and explored was during a period in which the hill was largely untouched since the activities of the Simcoes and others, but would be on the cusp of major changes. The last two decades of the 1800s saw a transformation of and debate over the future of the hill and valley(s) below. As history moved into the following century, it would see an intensification in housing, three major public works projects, and an institutional additional – all that would change the complexion of the hill snd its surrounding area forever.

A New…and Newer Castle Frank

Walter McKenzie was the Clerk of the County Clerk for Toronto. He was also a former soldier. By the 1850s, he had taken up residence on Castle Frank Ridge. Along with a house, which he also called “Castle Frank,” there was an orchard and vineyard overlooking the Don River, located north of the spot where Mr. Simcoe built his cottage. It was the first permanent home on the hill since the ancient Castle Frank burned down in 1829.

In 1857, McKenzie placed an advertisement in The Globe selling “About Four Hundred Standing Pines,” located on the forested hill. McKenzie was a well-connected man in Toronto, particularly in the law profession; his son-in-law John Hoskins, also a lawyer, lived in the nearby “Dale” estate. Drumsnab, the other neighbour 19th century prominent estate, was also occupied by lawyers, first William Cayley and then Mr. Maunsell B. Jackson. McKenzie passed away in 1890.

Albert Edward Kemp was a very successful businessman who founded the Kemp Manufacturing Co., metal located at Gerrard Street East and River Street. In 1900, he entered federal politics, rising to prominence as Minister of Militia, a role that led to his knighting. In 1902, as a member of Toronto High Society, he built “New Castle Frank” on the site of McKenzie’s Castle Frank. Kemp died in 1929; his mansion stood until the 1960s.

Castle Frank Brook & Rosedale Valley Road

“Immediately under the site of Castle Frank, to the west, was a deep ravine containing a perennial stream known and marked on plans as ‘Castle Frank’ Brook, which entered the Don at one of the ‘Hog’s Backs’ referred to, where also was a small island form in the river…”
Henry Scadding, 1895

The Don River tributary known as Castle Frank Brook ran in a northwesterly direction to its heads near Dufferin and Lawrence. It is also known by other names: Severn Creek and Brewery Creek after the Severn Brewery, formerly located where the stream crossed Yonge Street. It also has gone by Davenport Creek, possibly because it passed through the Davenport estate.

Plans for a road and sewer through Castle Frank Brook ravine began in the late 1880s. The reasons for its transformation were twofold. First, following a general public health phenomenon in the city which called for the burial of polluted open waterways and creeks, it was decided to put Castle Frank Brook into a culvert. The creek’s state had deteriorated as the “northern district” had developed. Second, the idea of the road gained traction following a general movement towards “park drives” or “parkways.” The eventual Rosedale Valley Road married the two goals.

The Globe reported:

The plan for the Davenport Creek ravine drive provides that it shall leave the road near the Winchester street bridge, on the way to the Silver Creek drive, and descending in the ravine follow near the line of the present creek. After passing St. James Cemetery, the drive will go through the property of Mr. Walter Mackenzie. After crossing the Castle Frank road it passes through the property of John Hoskin, S James, Margaret James, H J Clark, J L Thompson, R K Burgess, Alfred Chapman, William Croft, George and James Murray and F E Hodgson.”
The Globe, March 5, 1887

In 1887, Toronto City Council approved the expropriation of “a sixty-six foot roadway through it [Rosedale Valley] on the local improvement principle and the laid the sewer in the new street.” St. James Cemetery agreed to give the city any lands without any cost to the city. In the 1890s, the area was graded and the necessary construction took place. Awards were made to property owners by the city.

But the road construction was not without controversy. The City expropriated parts of the estates listed above — or so it thought. A clerical error did not properly register the expropriation, making it and the opening of the street illegal. The by-law outlining the expropriation was sent to the Registry Office to be registered in 1888. However, it should have been accompanied by a plan by Unwin Sankey and Browne, showing the land to be expropriated so that the affected properties could be identified. The plan was not sent, and the expropriations were not registered. The error was not discovered until a decade later. Rosedale Valley Road was opened without officially expropriated the needed lands.

The affected owners protested about their requirement to pay their share to open the road. The idea seems to be that Rosedale Valley Road was to be opened as a ‘local improvement project’, meaning that affected residents of the area were supposed to fit the bill to build the road. With this error, the courts quashed residents of any obligations – effectively placing the City of Toronto and its general tax base on the hook. In early 1899, the city registered a new bylaw regarding Rosedale Valley Road, and the lawsuits continued regarding the “debentures” of the street. It is unclear how the matter was resolved.

In 1897, the road was described as “…one of the coolest, shadiest and most beautifully picturesque roads in or near this city.” It is a description that holds today.

In 1905, it was briefly proposed by Alderman McBride to make Rosedale Valley Road into a ‘speedway’ for horses from Park Road to Winchester Street. St. James Cemetery stated they would have never donated the land for the road if this would be the plan.

The Cemetery & The Park

St. James Cemetery opened in 1844 across the ravine opposite Castle Frank on donated land from the Scadding estate (previously the Simcoe estate). By 1897, a proposal existed to expand the cemetery’s grounds north of Rosedale Valley on Castle Frank Hill. The plan proved to be very controversial.

The proposal at heart looked to convert the land on Castle Frank Ridge into parkland and space for graves. The problem was the hill was subdivided with lots and owners by at least the start of the decade.

In 1897, Mayor Fleming and a contingent of politicians and ‘leading citizens’ toured Toronto by motorcar as they assessed potential park sites. They began at Queen Street and Logan Avenue. Reaching and crossing the Don, they scouted Sugar-Loaf Hill, a thickly wooded triangular hill that was said would make a picnicking area as part of the ‘Parks Plan.’ Next, they noted “the steep and wooded eastern side of Castle Frank, for the securing of which the Mayor is negotiating with owners of the St. James’ Cemetery, who have bought that whole district from Dr. Hoskin.” This latter point is important as it signaled a disputed future for Castle Frank Hill.

A NATURAL PARK

As one drives up the Ravine road on the right hand, as far east as the Don, all this territory, undesecrated by the end of man, with its three and a half acres of indescribably lovely side-hills and twenty-three acres acres of additional property on the summit, is to be virtually owned as a public park by the city of Toronto on certain conditions.

The three and a half acres is to be a gift to the city from Dr. Hoskin. The owners of the St. James’ Cemetery will control the flat at the top and provide for its beautification and maintenance. They ask that the city allow them to use the level land on the Castle Frank eminence as a burial ground, and that the city build a road from the drive to the top of the hill, so that a hearse can safely ascend the incline. This road will cost about $2,000 and a fence to enclose the whole cemetery park another $1,000. This is really the sole cost to the city for this magnificent park.
The Evening Star, July 17, 1897

In September 1897, the owners of lots 28 to 31 Castle Frank Avenue made a protest to the city about the cemetery extension, which they argued would destroy their property as it would be located adjacent against a cemetery.

Then, a Mrs. Mary Hebden, owning 10-13 Castle Frank Avenue of plan 686, filed a formal suit:

“…to restrain the city and the churchwardens of St. James’ from passing any by-law or resolution to permit burial on any of these lots, or to allow the churchwardens to enlarge the cemetery, or to perform any interments within the city limits, outside the limits of the present cemetery.

It also sought to prevent the city from amending any standing by-law as to burials within the city limits.”
The Evening Star, October 19, 1897

Mrs. Hedben’s suit against the city was heard several months later. Her lawyer, Mr. Hodgins, asked for an order to prevent the cemetery from adding more lands and for any agreement to exist between the cemetery and the city. This was denied as City Council could vote how it wanted. Hodgins then argued a statute that prevented cemeteries from being established within city limits but the law did not apply either.

In October 1897, the cemetery was anxious to have the by-law passed. Its trustees met with the City Board of Control to negotiate terms. City Council also met at the Castle Frank table to go over the boundaries of what would be park and what would be cemetery; property owners, led by Mr. Jackson of Drumsnab, were there to protest. By November, talks between the city and cemetery had broken off as the city found the trustees unreasonable in their terms. The cemetery in the meantime began to make arrangements with Dr. Hoskins to bury in the property they did own. Eventually the scheme was dropped entirely by the city. The matter was finally reopened in the following October with new negotiations.

In December 1898, the Globe reported the City had finally reached an agreement with St. James Cemetery to add forty-two acres of parkland in the Rosedale Ravine. At a special Board of Control meeting to discuss the plan, Mr. Jackson again argued his objections, stemming from a loss of taxes on would-be property, the need for a clause to compensate property owners, and a letter from medical men advocating that cemeteries should not be established within city limits. The agreement was referred to council.

By early 1899, it was advertised The McIntosh Granite and Marble Co. a mausoleum built on the Castle Frank section of the cemetery for a W.R. Brock, Esq. In July, the city and cemetery entered into an agreement for the city to lease some cemetery property for parkland in return for permission to bury in Castle Frank. It was opposed by a Mr. J. G. Ramsey who owned property at Castle Frank and Mackenzie Avenues and argued it would “render his property comparatively valueless.” A very animated Mr. Jackson also spoke against it. The plan was sent to council without recommendation as no consensus was reached.

Curiously, as the city moved into the twentieth century, the records are silent on what happened next regarding this contentious episode. It must be noted that by the end the decade and into the 1910s, houses began to sprang up on Castle Frank Avenue on the ridge and there are no references to the cemetery. The City of Toronto today lists the area south and east of the street as parkland.

The Bloor Viaduct

While the earliest mention of a bridge across the Don Valley joining Bloor Street and Danforth Avenue was in 1897, proposals on how to make it happen came about in the following decade. With the likely need to traverse Rosedale Valley as well, Castle Frank Hill would become an important part of the project. One idea involved two bridges running west and east from Castle Frank Crescent, connecting with Howard Street over Rosedale Valley and Winchester Street over the Don Valley, respectively. However, a prominent idea was put forward by City Engineer C.H. Rust which recommended a one mile-long bridge straight from Sherbourne Street to Broadview Avenue and another shorter viaduct extending from Parliament Street to meet it a “T”. Arguments over the impact it would have on Rosedale Valley by the Guild of Civic Art and Civic Improvement Committee as well as Rosedale resident concerns led to a “no” vote in referenda in 1910, 1911, and 1912.

Sources: The Toronto Daily Star, Nov 28, 1906; The Toronto Daily Star, June 6, 1917; The Globe, Dec 29, 1910; The Globe Dec 28, 1911; The Globe Jan 1, 1913

On January 1, 1913, the Toronto electorate voted to finally build the Bloor Viaduct. Construction began officially in 1915, although preliminary work was done in the years that preceded. The eventual design relied on two separate bridges to cross both ravines as well as the extension of Bloor Street between Sherbourne and Parliament Streets, which would be facilitated by landfill terraces. The bridges consisted of a ‘diagonal’ Rosedale section between Parliament to Castle Frank and a ‘straight’ Don section between Castle Frank and Broadview Avenue. Both sections were similar in aesthetic, made of concrete and steel, and highlighted by large arches. A lower level for a future streetcar line was added to both bridges. The bridge opened in sections with the entire structure – officially The Prince Edward Viaduct – being available on October 18, 1918.

The eventual changes to the geographic imprint of the area extended past just the additions of the new bridges and roads. In order to facilitate those additions, several losses had to take place. There were several residences razed for the Bloor Street extension, including the Castle Frank gatehouse at Parliament Street, its neighbour at 102 Howard Street, and other structures at Glen Road and Sherbourne Street. On the Castle Frank Hill, it appears that at least one or two residences on Castle Frank Road — such as number 87 — were lost where the new street was set to go in and parts of other lots gave way for the new street layout. In 1922, Castle Frank Road south of the Bloor Viaduct was renamed to Castle Frank Crescent (ironically, a name it once held before it was combined into Castle Frank Road).

Castle Frank, pre and post-Bloor Viaduct, 1913 & 1924.
Source: Goads Toronto

The Don Valley Parkway & The Destruction of Sugar Loaf Hill

The middle of the 20th century saw a string of major civic projects which would collectively change the local complexion of the Castle Frank Region. The first of these was a freeway through the adjacent Don Valley. Planning began in 1954. This would be a different kind than the parkway built through the Rosedale Valley nearly sixty years prior. In the lower valley, the project consisted of the main highway which would run on the east side of river and the southern extension of Bayview Avenue running parallel to it on the west side of the river beside the train tracks.

A product of the creative destruction of the Don Valley Parkway was the removal of Sugar Loaf Hill, the conical mound located north of Castle Frank that the Simcoes, E.T. Seton, and Charles Sauriol all noted and explored. It would be levelled to make way for the Bayview Extension. Several lamenting articles appeared in newspapers over the event. In 1958, during the construction of the highway, Globe writer Scott Young wrote:

“Soon it will be gone and fast bright cars on the Don Valley Parkway will stream north and south over one more vanished place where boys once roamed alone, every step an adventure, and even the crows had names.”
Scott Young, The Globe and Mail, May 8, 1958

Young also spoke to Charles Sauriol about the loss:

“As he says, nobody seriously contends that a hill that few people ever even look at, or use much (although a worn path twisting to Sugar Loaf’s top ends now suddenly in the wake of a bulldozer) should stand in the way of a needed roadway.

Yet it is an item of history. Going, going, gone.”

Young, like Ron Haggart writing for the Toronto Daily Star, referenced E.T. Seton and Silverspot. Haggart was writing on the eve of the opening of the Don Valley Parkway in August 1961:

It will be open in time for the afternoon rush hour. And, not seeing with the same eyes as Ernest Thompson Seton, we can drive over the 137,000 tons of asphalt which now lay in the Don Valley, skirting the Don River bright with the chemicals of the paper mill under the 600 towers of the fluorescent lighting standards, which never will house an old hawk’s nest known by every school boy.

‘I’ll tell you what the Don Valley was,” Frederick Gardiner said once, when someone on his Metropolitan council, mourned for the passing of the woods by Castle Frank, “the Don Valley was a place to murder little boys, that’s what it was”
Ron Haggart, The Toronto Daily Star, August 30, 1961

Frederick “Big Daddy” Gardiner was the Chairman for Metro Toronto Council and was a bold and controversial figure who was involved in several public works projects, including the Don Valley Parkway and the elevated downtown highway which would later bear his name.

The DVP’s other impact was a long offramp for the Bayview/Bloor exit that would wind its way across the valley and down to Castle Frank Road. The ramp would absorb part of the Drumsnab property (the old estate house is visible on the right as one drives south on the ramp) as well as part of Drumsnab Road.

Castle Frank area, 1963.
Source: City of Toronto Archives

A New Subway

The next time a major infrastructure project touched Castle Frank was in the 1960s, when an east-west, cross-town subway line was planned for Toronto. With the Bloor-Danforth corridor ultimately chosen for the project, decisions would need to be made about how it would cross the Don and Rosedale Valleys and a location for the station itself. Construction began in 1962.

As a cost-cutting method, the route was chosen to run under the lower deck of the existing viaduct. At least, it would be on the Don section. The turns on the Rosedale section were deemed too sharp for trains. Thus, a separate structure – a covered bridge – ran between Castle Frank Station and the infilled Bloor Street over Rosedale Valley. The elevated tunnel was encased to minimize noise concerns for the nearby Kensington Apartments (which were incidentally built on the site of John Hoskin’s Dale, demolished in the 1940s or 50s).

The station itself was built on the northwest corner of Bloor Street East and Castle Frank Road. At least four residences were removed to make space for the station and a bus station. The station opened on February 26, 1966 along with the rest of the line.

The Castle Frank School

Lady Kemp passed away in 1957, twenty-eight years after her husband, Sir Edward Kemp. Their palatial Castle Frank was put up for sale; executors of her estate put a sale price of $1.2 million. The City of Toronto, Metro Council, and the Toronto Transit Commission turned down opportunities – likely because of the price tag – to turn the site into a park, a parking garage, or a subway station. The Toronto Civic Historic Society pitched to Ontario Premier Frost to turn it into a residence for the Lieutenant-Governor. It was also proposed as a museum for York County.

The emerging proposal came from prolific Toronto developer Reuben Dennis in late 1958. His vision was to raze the mansion to erect a 21-storey, 972-unit luxury apartment building. Residents of Castle Frank Crescent, whose homes backed onto the property, opposed the rezoning of the single-family residential area. The affected residents included some of Canada’s most prominent citizens, such as former Prime Minister Arthur Meighen, Mr. Justice Gibson of the Ontario Court of Appeal, Lew Haymen, the managing director of the Toronto Argonauts, and Mrs. H..J. Cody, the wife of the late former president of the University of Toronto. The residents – who called the plan “ghastly, revolting, and a great pity” – organized into the South Rosedale Ratepayers. The battle continued in 1959 with the Toronto Planning Boarding rejecting the application and the Ontario Municipal Board being asked to change the zoning.

By July 1960, Castle Frank was back on the market. The new plan was for a vocational type school for a “lower middle group of secondary school-age pupils and others who do not plan to go university.” The Kemp estate accepted a $700,000 offer. The Globe and Mail described:

In the beginning, Castle Frank will operate with an experimental program designed to build up an approved curriculum for its 500 students. The new Boulton Avenue School could become the second of this type in Toronto.

Castle Frank and the junior vocational schools are based on the concept that slow learning or emotionally disturbed pupils have a special place in a modern society with a rapidly changing technology.

Castle Frank also takes into account that there are many intelligent students who do not want to go to university and need some educational medium other than the existing academic, technical or commercial high school
The Globe and Mail, November 17, 1960

Castle Frank School was opened in 1963. It operated until the 1990s when “an organized abandonment” led to a change in model. A rebrand in name also came with the move: Rosedale Heights Secondary School, later Rosedale Heights School For the Arts. The institution that stands today, housing a salvaged piece of the Kemps’ residence and a plaque. The principal at the time of the shift hoped to name the new school after Elizabeth Simcoe.

Remembering Castle Frank

Today, the Simcoes’ 1790s summer residence is honoured in name by Castle Frank Road, Castle Frank Crescent, and Castle Frank Subway Station. In 1954, the Don Valley Conservation Authority (of which Charles Sauriol was a member) erected a cairn dedicated to Castle Frank in Prince Edward Viaduct Parkette on the south side of Bloor Street. The monument dons the image of the home and reads:

“Castle Frank

The country home of Lieutenant Colonel John Graves Simcoe first Lieutenant Governor of Upper Canada 1791-1796, stood on these heights just south of this site 1794-1829. Named after Francis Gwillim Simcoe, son of Lieutenant Governor and Mrs. Simcoe, who died in the year 1812, serving under the Duke of Wellington.”

The Ontario Heritage Trust also erected one of their iconic blue plaques in honour of Elizabeth Simcoe. It stands inside the grounds of the Rosedale Heights School, which might have bore her name at one time. The plaque says:

“ELIZABETH POSTUMA SIMCOE 1766 – 1850

The wife of the first Lieutenant-Governor of Upper Canada, Elizabeth Posthuma Gwillim was born at Whitchurch, Herefordshire, England. Orphaned at birth, she lived with her uncle, Admiral Samuel Graves, and subsequently married his god-son, John Graves Simcoe. She accompanied her husband to Upper Canada where she travelled extensively. Her diaries and sketches, compiled during these years, provide a vivid description and invaluable record of the colony’s early life. In 1794, near this site, Mrs. Simcoe and her husband erected a summer house which they named “Castle Frank” in honour of their son. Returning to England in 1796, Mrs. Simcoe devoted her later years to charitable work. She is buried beside her husband at Wolford Chapel, Devon.”

Castle Frank, in its post-contact era, began as a beautiful hilltop locale, hand-picked by Toronto’s top administrator to house his residence. The layers of activity over the next two centuries continued to prove its desirability, facilitated in part by its central location and unique situation between two valleys. These commemorations mark a place and people important to the early colonial history of Toronto. The events that point in time added intriguing layers which together tell an interesting story.

Sources Consulted

“About The City.” The Globe, 3 June 1890, p. 8.

“Apartments Planned for Historic Site.” The Globe and Mail, 18 Dec. 1958, p. 5.

“Ask OMB to Amend Castle Frank Zoning.” The Globe and Mail, 30 Oct. 1959, p. 4.

Bateman, Chris. “That Time Toronto Opened the Don Valley Parkway.” blogTO, blogTO, 10 Aug. 2013, http://www.blogto.com/city/2013/08/that_time_toronto_opened_the_don_valley_parkway/.

Bateman, Chris. “The Modernist Bloor-Danforth Line at 50.” Spacing Toronto, 25 Feb. 2016, spacing.ca/toronto/2016/02/25/subway-modern-at-50/.

Berchem, F. R. The Yonge Street Story: 1791-1860: An Account from Letters, Diaries and Newspapers. Natural Heritage/Natural History, 1996.

“The Bloor Street Viaduct.” The Globe, 13 June 1913, p. 6.

“The Bloor Viaduct Conference.” The Globe, 19 Jan. 1912, p. 6.

Bonnell, Jennifer. Reclaiming the Don: An Environmental History of Toronto’s Don River Valley. University of Toronto Press, 2014.

Boylen, John Chancellor. The Story of Castle Frank, by J.C. Boylen. Illus., from Original Sketches Painted by Mrs. John Graves Simcoe.

Brace, Catherine. “Public works in the Canadian city; the provision of sewers in Toronto 1870–1913.” Urban History Review, vol. 23, no. 2, 1995, pp. 33–43, https://doi.org/10.7202/1016632ar.

Cabbagetown Uncovered: Simcoe Family Built Castle Frank … – Toronto.Com, http://www.toronto.com/news/cabbagetown-uncovered-simcoe-family-built-castle-frank-in-the-wilderness-near-the-don-river/article_77f1bdbc-722d-54d4-b638-d34a0ca2b7d4.html. Accessed 4 Jan. 2024.

“Canada.” The Globe, 13 Sept. 1871, p. 4.

“Castle Frank Apartment Plan Turned Down.” The Globe and Mail, 6 May 1959, p. 5.

Castle Frank, http://www.lostrivers.ca/points/CastleFrank.htm. Accessed 3 Jan. 2024.

Caswell, Thomas. “Notice Is Hereby Given.” The Globe, 21 Jan. 1899, p. 8.

“Cemetery Deal Off.” The Globe, 1 Nov. 1897, p. 5.

“The City Is Leading.” The Evening Star, 18 Nov. 1897, p. 1.

City of Toronto. “Bridging the Don: The Prince Edward Viaduct.” City of Toronto, 14 Apr. 2023, http://www.toronto.ca/explore-enjoy/history-art-culture/online-exhibits/web-exhibits/web-exhibits-architecture-infrastructure/bridging-the-don-the-prince-edward-viaduct/.

“City’s Proposed Plan For Crossing The Rosedale Ravine – And Another.” The Globe, 29 Dec. 1910, p. 7.

“Colleges Free of Taxes.” The Globe, 22 Oct. 1897, p. 5.

Commemorative Biographical Record of the County of York, Ontario: Containing Biographical Sketches of Prominent and Representative Citizens and Many of the Early Settled Families, Illustrated. J.H. Beers, 1907.

“Company Plans Caste Frank Veto Appeal.” The Globe and Mail, 14 May 1959, p. 5.

“Council Must Decide.” The Globe, 21 Oct. 1897, p. 5.

“Council Passes St. Lawrence Market Report.” The Evening Star, 21 July 1899, p. 8.

Don River Valley Historical Mapping Project, maps.library.utoronto.ca/dvhmp/castle-frank.html. Accessed 3 Jan. 2024.

Early Canada Historical Narratives — John Graves Simcoe, http://www.uppercanadahistory.ca/simcoe/simcoe1.html. Accessed 3 Jan. 2024.

“Evocative Images of Lost Toronto.” UrbanToronto, UrbanToronto, 19 Nov. 2023, urbantoronto.ca/forum/threads/evocative-images-of-lost-toronto.11018/page-170.

“The Expensive By-Law Plan, and Another.” The Globe, 28 Dec. 1911, p. 7.

Filey, Mike. Toronto Sketches 3: “The Way We Were.” Dundurn Press, 1994.

“Finds Building Apartments Fascinating Job.” The Globe and Mail, 27 Oct. 1959, p. 18.

“A Fine New Park.” The Evening Star, 11 Oct. 1898, p. 8.

“For A Drive in Rosedale.” The Globe, 11 Dec. 1905, p. 7.

“For Public Park.” The Globe, 10 Dec. 1898, p. 17.

“For Sale.” The Globe, 1 Jan. 1857, p. 4.

“Governments Share Costs of Castle Frank School.” Toronto Daily Star, 29 Mar. 1961, p. 39.

Haggart, Ron. “Earnest Thompson Seton And The New Parkway.” Toronto Daily Star, 30 Aug. 1961, p. 7.

Hamilton, James Cleland. Osgoode Hall–Reminiscences of the Bench and Bar. Nabu Press, 2010.

Henderson, Elmes. “BLOOR STREET, TORONTO, AND THE VILLAGE OF YORKVILLE IN 1849 .” PAPERS AND RECORDS, Ontario Historical Society, XXVI, 1930, pp. 445–456.

“Here’s A Pretty Mess.” The Globe, 2 Nov. 1898, p. 8.

“A Historic Landmark.” The Globe, 28 Mar. 1928, p. 4.

“Horses and Cemetery.” Toronto Daily Star, 3 Feb. 1905, p. 7.

“In Commitees.” The Globe, 10 Mar. 1899, p. 8.

“In Committee.” The Globe, 8 Mar. 1899, p. 4.

Information Regarding Doctor John Hoskin K. C. , L. L. D. & His/Her Family, harris-history.com/tree/2226.html. Accessed 3 Jan. 2024.

Jones, Morland. “Fight Seen Over Historic Site: Plan to Raze Castle Frank Estate For 21-Story Luxury Apartments.” The Globe and Mail, 18 Dec. 1958, pp. 1–2.

“Lady Kemp’s Will $481,549, Kin to Get Husband’s 7,718,000.” Toronto Daily Star, 1 Oct. 1957, pp. 1–2.

“Lamb on the Defensive.” The Globe, 21 Sept. 1897, p. 5.

“The Law and the Graves.” The Evening Star, 19 Oct. 1897, p. 1.

“Letter to Sir Joseph Banks (President of the Royal Society of Great Britain) Written by Lieut.-Governor Simcoe, in 1791, Prior to His Departure from England for the Purpose of Organizing the New Province of Upper Canada.” Google Books, Google, http://www.google.ca/books/edition/Letter_to_Sir_Joseph_Banks_president_of/TZUOAAAAYAAJ?hl=en&gbpv=1&dq=%22parliament%2Bstreet%22%2B%22castle%2Bfrank%22&pg=PT3&printsec=frontcover. Accessed 3 Jan. 2024.

“Link to the Past Severed by Death.” The Toronto Daily Star, 28 July 1927, p. 9.

“Local News.” The Globe, 26 Apr. 1887, p. 8.

Lundell, Liz. The Estates of Old Toronto. Boston Mills Press, 1997.

MacIntosh, Robert. Earliest Toronto. General Store Pub., 2006.

“Madge Merton’s Page.” The Toronto Daily Star, 22 Sept. 1900, p. 12.

“Minutes of Proceedings of the Council of the Corporation of the City of Toronto.” Google Books, Google, books.google.ca/books?id=tr1EAQAAMAAJ&pg=RA3-PA510&dq=bloor%2Bviaduct%2Bexpropriation&hl=en&newbks=1&newbks_redir=0&sa=X&ved=2ahUKEwj-3Za9s5eDAxW3BDQIHY__Bs8Q6AF6BAgKEAI#v=onepage&q=bloor%20viaduct%20expropriation&f=false. Accessed 3 Jan. 2024.

Murnaghan, Ann Marie. “The city, the country, and Toronto’s Bloor Viaduct, 1897–1919.” Urban History Review, vol. 42, no. 1, 2013, pp. 41–50, https://doi.org/10.3138/uhr.42.01.03.

Murnaghan, Ann. “The City, the Country, and Toronto’s Bloor Viaduct, 1897–1919 – Urban History Review / Revue d’histoire Urbaine.” Érudit, Urban History Review / Revue d’histoire urbaine, 3 Feb. 2014, http://www.erudit.org/en/journals/uhr/2013-v42-n1-uhr01125/1022058ar/.

“‘Never Wanted to Do Anything Else’: Toronto Principal Marks 40+ Years at the Helm.” Toronto, CTV News, 2 May 2023, toronto.ctvnews.ca/never-wanted-to-do-anything-else-toronto-principal-marks-40-years-at-the-helm-1.6380455.

“New Homes in Toronto.” The Globe, 18 Jan. 1913, p. A1.

“The New Market.” The Globe, 13 July 1893, p. 7.

“New Plan to Bridge The River Don.” The Toronto Daily Star, 17 June 1907, p. 6.

“Now The Market.” The Globe, 14 July 1899, p. 6.

“Opposes The Park.” The Evening Star, 14 Dec. 1898, p. 1.

Osbaldeston, Mark. Unbuilt Toronto a History of the City That Might Have Been. Dundurn Press, 2008.

“The Parks Plan.” The Evening Star, 17 July 1897, p. 5.

“Parks The City Should Have.” The Toronto Star, 17 July 1897, p. 4.

“Parliament Buildings of Ontario.” The Globe, 30 May 1893, p. 4.

“Plan for the Proposed Bloor Street Viaduct.” The Globe, 1 Jan. 1913, p. 8.

“Preparation Are Made For Bloor Street Viaduct.” The Globe, 2 June 1914, p. 9.

“Ravine Bridge Scored.” The Globe, 22 Dec. 1909, p. 5.

“The Ravine Drives.” The Globe, 5 Mar. 1887, p. 16.

READ, D. B. Life and Times of Gen. John Graves Simcoe: Commander of the “Queen’s Ranger’s” during the… Revolutionary War, and First Governor of Upper Can. FORGOTTEN BOOKS, 2018.

“Real Estate Now Is Satisfactory.” The Toronto Daily Star, 19 Jan. 1901, p. 7.

“Revised Subway Plan Approved by Board.” The Globe, 29 Oct. 1960, p. 3.

Robertson, J. Ross. Landmarks of Toronto: A Collection of Historical Sketches of the Old Town of York from 1792 until 1833, and of Toronto from 1834 to 1898. Mika, 1974.

“Rosedale and the Cemetery.” The Globe, 18 Sept. 1897, p. 20.

“Rosedale and The Cemetery.” The Globe, 25 Sept. 1897, p. 6.

“Rosedale Valley Drive.” The Globe, 11 Nov. 1898, p. 4.

Sauriol, Charles, and Vivian Webb. Tales of the Don. Natural Heritage/Natural History Inc., 2016.

Sauriol, Charles. Remembering the Don: A Rare Record of Earlier Times within the Don River Valley. Consolidated Amethyst Communist Communications, 1981.

Scadding, Henry. Supplement to Rev. Dr. Scadding’s Story of Castle Frank, Toronto. 1896.

“Seeking A Route For The Viaduct.” The Globe, 29 Jan. 1912, p. 9.

Senter, James. “Vocational-Type School Planned for Castle Frank Site: Estate Accepts $700,000 Offer.” The Globe and Mail, 10 Nov. 1960, p. 5.

Seton, Ernest Thompson. Wild Animals I Have Known. Gibbs Smith, 2020.

Simcoe, Elizabeth, and Mary Quayle Innis. Mrs. Simcoe’s Diary. Dundurn, 2007.

Smith, Anne. “‘Let’s Keep What’s Left of Rosedale.’” The Globe and Mail, 24 Dec. 1958, p. 6.

“Special Committee Approves: Replacement Planned for Boulton.” The Globe and Mail, 17 Nov. 1960, p. 5.

St. John, J. Bascom. “THE WORLD OF LEARNING: PROGRAM FOR DROPOUTS.” The Globe and Mail, 14 May 1964, p. 7.

“Story of Castle Frank.” The Globe, 8 May 1895, p. 6.

“That New Hotel.” The Globe, 1 July 1899, p. 32.

“Three Proposals to Cross Ravines to North-West Section.” The Toronto Daily Star, 28 Nov. 1906, p. 8.

Toronto of Old, by Henry Scadding – Gutenberg, gutenberg.ca/ebooks/scadding-torontoofold/scadding-torontoofold-00-h-dir/scadding-torontoofold-00-h.html. Accessed 4 Jan. 2024.

“Two Contracts For Subway Are Awarded.” The Globe and Mail, 16 Jan. 1963, p. 4.

“Two Streets, But One Name.” The Globe, 26 Sept. 1922, p. 13.

“Under Rough Roof, Gay Days: Cairn to Mark Site Of Simcoe’s Castle.” The Globe and Mail, 6 Mar. 1954, p. 10.

“W.A. Murray & Co.” The Globe, 2 Jan. 1899, p. 7.

Westall, Stanley. “Metropolitan Toronto: A Castle on Bloor St.” The Globe and Mail, 28 July 1960, p. 7.

“Will Fight Rezoning Of Castle Frank Area.” The Globe and Mail, 11 Feb. 1959, p. 5.

“A Winchester Viaduct.” The Globe, 3 Feb. 1912, p. 6.

“Would Buy Land For Viaduct.” The Globe, 26 Mar. 1912, p. 9.

“Writing the Environmental History of Toronto’s Don Valley Parkway.” Jennifer Bonnell, jenniferbonnell.com/writing-the-environmental-history-of-torontos-don-valley-parkway/. Accessed 3 Jan. 2024.

YEIGH, FRANK. Ontario’s Parliament Buildings: Or a Century of Legislation, 1792-1892. FORGOTTEN BOOKS, 2018.

“York Pioneers.” The Globe, 1 Feb. 1870, p. 1.

Young, Scott. “In the Road: Sugar Loaf Soon Thing Of Memory.” The Globe and Mail, 8 May 1958, p. 27.

2022: A Year in Review

2022 marks ten years for Scenes From Toronto. This year, I committed to a goal of two articles a month when possible. Out of 24 possible articles in the month, I published 17. Although I did not match my goal, I am proud of that output.

2022 also followed the momentum of the previous year in creating original, research-based articles, drawing on primary and secondary sources, as well as the work of great historians and writers. I hope they have added to Toronto’s rich local heritage scene and telling the city’s lesser known (hi)stories.

The Stats

The Best of 2022

To mark the year, I have compiled my favourite ten articles.

1. “Old” Toronto Streets: An exploration of a peculiarity in Toronto’s geography and streets. This is a multi-parter.

2. A Quick Early History of Toronto’s First Traffic Signals and The ‘Right on Red’ Rule: Toronto’s early rules about automobile travel offer some interesting insights about why modern traffic laws are the way they are, including the origins of the allowance of a right turn against a red light.

3. “Know Agincourt, but Their Maps Ignore Toronto”: A Quick History of The Agincourt Magnetic Observatory: The story of a lost Scarborough landmark which brought on discovery and innovation at a global level.

4. A Quick History Of The Iconic Guild Inn in Scarborough: The Guild of All Arts is a famed landmark is the east end of Scarborough with an interesting evolution.

5. The ‘Commercial Slum’ That Once Stood Across Toronto City Hall: This is a layered story of the creative destruction and revitalization which marked an intriguing transitional period in Toronto. The first of two parts.

6. The Rise of The Hill District, Toronto: The origin of one of Toronto’s exclusive neighbourhoods is an interesting tale of the who’s who in Toronto history and a period in which Old Toronto’s street grid began to fill up.

7. Was this the first Chinese restaurant in Toronto’s Junction?: A century ago, there was a Chinese eatery in The Junction. The story explores some history of one of Toronto’s largest communities.

8. The Curious History of Riverdale Avenue, Toronto: The east ends street is a fine reminder of how old lot lines have impacted the look of the city.

9. A Quick History of Controversial Toronto Street Name Changes: In a topical subject, this explores some lesser known street name changes and some overall in themes in why streets are historically altered.

10. The Notorious Brooks’ Bush Gang: A feared group of trouble-makers terrorized 19th century Toronto. A second part to this story is coming.

Thanks to all that have read, engaged with, and supported Scenes From TO! Happy 2023!

How The Sheraton Centre In Toronto Was Built

Note: This article is the second piece in a two-part series. The first can be found here.

In the 1960s, Toronto had a big question to address: “What would replace the commercial section across The New City Hall?” What followed was action to remove the Queen Street shops between Bay and York Streets and replace them with a complementary project worthy of the new civic centre.

The Expropriation Question

As Toronto entered the 1960s, progress on the Queen Street question seemed slow. In October 1960, there were reports that demolition would begin in the autumn of 1961 or spring of 1962 on the “seedy” south side. The Planning Board was preparing an invitation to attract private developers to redo the site. However, in May 1962, this draft invitation was presented to city council for approval. City Council now had the estimate down to $6,250,000 to buy the properties, but the The Globe and Mail anticipated difficult negotiations with property owners, particularly with the Municipal Hotel and Casino Theatre, who where the largest land owners on the block. The city approved a motion to start expropriating properties, but it was unclear whether this was a path to be taken.

For the Municipal Hotel, owner Arthur Mintz was not going along with city plans to redevelop his property. He had his own project: a three million dollar, 14-storey office tower to replace the hotel. Mintz’ hotel was key in building an office tower at Queen and Bay, but the owner was not going to sell at even a reasonable price to a developer, instead opting to go at it alone. A by-law was passed indicating that whatever new development went through on Queen, the ends of the strip would have towers while the middle would be lower so not to “spoil the view” of the new city hall. The holdup? Owners of these central lots were unwilling to sell. The Daily Star’s editorial section and others advocated for expropriation.

Redevelopment

On August 12, 1964, Toronto City Council voted 17-4 to expropriate most of the block bounded by Queen, Richmond, Bay, and York Streets. Mayor Phillip Givens, a pro-development politician, was a large proponent of the expropriation option and the redevelopment of Queen Street as a whole. It was the first time in Toronto history in which the city opted to expropriate land to sell to private interests rather than execute a public project. Development Commissioner Walter Manthorpe warned that renewal was still another 10 years away with steps needing to be taken to take seek Ontario Municipal Board approval for the expropriation, take possession of the properties, demolish them, sell to developers, and come up with a redevelopment plan for the province’s approval. Proposals started to come in which would the potential form the site and Queen Street in general would take, including an interesting plan which would see a tunnel under Queen and the surface turned into a pedestrian mall between Yonge and University.

Much like the civic centre on the north side of Queen, the city decided to hold a design competition for the block leftover by the soon-to-be expropriated and demolished shops. The eastern end of the block would not be part of the project. In November 1964, Mintz sold the Municipal Hotel to a private developer, Reuben Dennis. The other properties included the Victory Building on Richmond St., the Temple and Dominion Bank Buildings on Bay St., and the Hamilton Trust property on Queen Street, the latter of which suffered a fire in 1963 and which Dennis also bought.

On September 13, 1965, the new City Hall and Nathan Phillips Square was revealed to Torontonians. The winning space-aged design by Finnish architect Viljo Revell consisted of two curved towers of differing heights, a central ‘oyster’ housing the council chamber, and a large open space with a wading pool, arches, public art, and a podium.

79-83 Queen Street West, showing Harry’s Men’s Shop and Vanguard Bookstore in the Frankel Building, and Lawrence Credit Jewellers on the west side of the Broadway Theatre, 1965.
Source: City of Toronto Archives

Across the street, there were some empty storefronts and vacant lots. For the shops that remained, there were ‘expropriation sale’ signs. By the next year, most of the block was razed to the ground and replaced by a level surface of sod and sidewalk.

In 1968, a mini-saga began in who would receive the rights to redevelop the property, which council was to rent out to the winning developer for 99 years. In April 1968, City Council approved a proposal which would see Third Generation Realty Limited build a $50-million hotel-convention centre on the three-and-a-half acre property. However, the Finance Commissioner determined Third Generation did not have the financial proof to back its proposal. In July, Council voted again, this time approving a $34-million scheme by Inn on the Park-Four Seasons, the other bidder in the April vote. During the event, an alderman was even accused of accepting a bribe, which he denied. In 1969, construction began on the 43-storey, 1,400-room hotel, which would become the Four Seasons-Sheraton Hotel. John B. Parkin Associates, who worked on City Hall, designed the complex.

Welcome to the Sheraton-Four Seasons Hotel

In 1972, the Sheraton-Four Seasons Hotel opened (the ‘Four Seasons’ would be dropped in 1976 as the hotel pulled out of the venture), the culmination of a 15-year saga to renew the Queen Street West strip across Toronto’s new municipal hub. Carrying the memorable street address ‘123 Queen West’, it was the second largest hotel in Toronto at the time of opening behind only the iconic Royal York Hotel (it was surpassed by the Chelsea Delta which opened only a few years later).

Conforming with the by-law from a decade earlier, the main hotel tower is situated off to the side of the city hall and square towards York Street, offering an unobstructed vista. The eastern side of the block saw the erection of a two-storey TD bank branch and the Queen-Bay Centre, consisting of the 25-storey Thomson Building and the Munich Re Centre, opening in 1972 and 1973 respectively. The latter building opened on the site of the demolished Temple Building, whose fragments are found at the Guild Inn Park.

In 2022, at fifty years old, the Sheraton Centre is a unique modernist, Brutalist construction. Its central area forms an atrium of waterfall gardens designed by J. Austin Floyd, the famed landscape architect who also left his footprint at the famed yet now lost Inn on the Park hotel at Leslie Street and Eglinton Avenue.

On the Queen Street mega-hotel, architect Michael McLelland wrote how “metropolitan structures like the Sheraton Centre are an integral part of the downtown morphology”. Its views of the complex across the street, which was the catalyst of its construction, are unparalleled in Toronto.

The Sheraton Centre and Toronto City Hall are fine examples of Toronto as a city made and re-made. They mark the ‘creative destruction’ of the post-war years. The south side of Queen Street between Bay and York was an interesting mix of establishments, many with varying stories and origins. The condemning of the strip as a ‘commercial slum’ and its subsequent replacement offers a complicated takeaway. On the one hand, the physical erasure has understandably hidden those histories from collective consciousness; on the other, the emergence of the Sheraton Centre has offered Toronto a marvel in itself. For better or worse, Toronto was growing up after World War II — in area, age, building heights, and architectural styles. The construction of the Sheraton Centre was in itself a microcosm of this period of transformation — and the representative of the expendability of centrally-located, culturally- and socially-colourful sectors like this one.

Works Consulted

[@ebloor]. “Twitter Message.” Twitter, 16 Aug. 2022. https://twitter.com/e_bloor/status/1559665299170816000?s=20&t=GT0tG6pTd3ZA5qCfAWQD4Q

[@raydonlive]. “Twitter Message.” Twitter, 16 Aug. 2022. https://twitter.com/raydonlive/status/1559626188485758979?s=20&t=GT0tG6pTd3ZA5qCfAWQD4Q

“10 Years to Renew Queen – Manthorpe.” The Toronto Daily Star, 14 Aug. 1964, p. 21.

“119 Church St.” Development Applications, http://app.toronto.ca/AIC/index.do?folderRsn=EuizkruJ6mXTxYPzkuYP2A%3D%3D.

“8-Story Building Queen St. Plan.” The Globe and Mail, 10 Sept. 1958, p. 5.

Baker, Alden. “Queen Street Project: Municipal Board Head Won’t Reopen Hearings.” The Globe and Mail, 24 Feb. 1968, p. B2.

Barr, Edward H. “Toronto’s Vanishing Chinatown.” The Globe and Mail, 9 Nov. 1957, pp. A21–A23.

“Bay-Queen Agreement Held Near.” The Globe and Mail, 22 Feb. 1966, p. 5.

Best, Michael. “Givens Sees His Shadow on His Queen Street Dream.” The Toronto Daily Star, 10 Feb. 1965, p. 28.

Best, Michael. “Special Report: Our New City Hall Will Face a Slum.” The Toronto Daily Star, 29 Dec. 1962, p. 1.

Best, Michael. “U.S Cities Clear Slums While We Flounder.” The Toronto Daily Star, 29 Jan. 1963, p. 7.

“Blueprint for Action.” The Globe and Mail, 10 Sept. 1958, p. 6.

Bradburn, Jamie. “From Eaton’s to Sears to Nordstrom.” Torontoist, 15 Jan. 2014, https://torontoist.com/2014/01/from-eatons-to-sears-to-nordstrom/.

Canadian Foreign Exchange Office. “Canadian Foreign Exchange Office.” The Globe, 18 Dec. 1920, p. 11.

Chan, Arlene. The Chinese in Toronto from 1878: From Outside to inside the Circle. Read How You Want, 2017.

“Charley Has A Bell: Wily Chinaman Prepares for Visits From Police.” The Toronto Daily Star, 19 Sept. 1904, p. 12.

“City Council’s Cue.” The Globe and Mail, 17 May 1958, p. 6.

“City’s Stake in Queen Street South.” The Toronto Daily Star, 16 July 1964, p. 6.

Enright, Michael. “Bewildering Episodes behind the Scenes of a Queen Street Hotel.” The Globe and Mail, 20 Apr. 1968, p. 7.

Filey, Mike. “The Way We Were: Sharing Photographic Memories of Henry’s.” Toronto Sun, https://theprovince.com/opinion/columnists/the-way-we-were-sharing-photographic-memories-of-henrys-as-camera-shop-closes-some-stores/wcm/410f17b8-c545-4a67-95a0-78ae1b5cf769.

Four Seasons Sheraton Hotel. “Something New in Toronto.” The Toronto Star, 28 Nov. 1972, p. 10.

“FOUR SEASONS HOTEL AT 12-STORY LEVEL.” The Globe and Mail, 13 Mar. 1971, p. B1.

“Gay History in Toronto.” UrbanToronto, UrbanToronto, 9 July 2014, https://urbantoronto.ca/forum/threads/gay-history-in-toronto.19918/.

Haggart, Ron. “How the Rubin Boys Lost Their Head Start.” The Toronto Daily Star, 13 Aug. 1964.

Hanrahan, William. “Grass in, Burlesque Out on Queen Street.” The Globe and Mail, 21 July 1965, p. 27.

“Hotel on Queen Street Approved as Piccininni Denies Bribe Offered.” The Globe and Mail, 6 July 1968, p. 1.

“Interview with X Tape 1, Side 1.” Alotarchives.org, https://www.alotarchives.org/locations-mentioned/denver.

“Inventor Is Promoted.” The Toronto Daily Star, 24 July 1917, p. 13.

“The Leading Issues.” The Globe and Mail, 13 Nov. 1954, p. 6.

LeBlanc, Dave. “A Brutal Trek through Toronto’s Brutalist Architecture.” The Globe and Mail, The Globe and Mail, 21 Apr. 2018, https://www.theglobeandmail.com/real-estate/toronto/article-a-brutal-trek-through-torontos-brutalist-architecture/.

Let Us Bring Your Friends From The Old Country. “Gurofsky’s Shipping Office.” The Toronto Daily Star, 1 Apr. 1920, p. 12.

Lipinsky, Jack. Imposing Their Will: An Organizational History of Jewish Toronto, 1933-1948. McGill-Queen’s University Press, 2011.

Lorinc, John. “The Slum We Buried in the Heart of Toronto.” The Globe and Mail, 23 May 2015, p. M1.

Lorinc, John, et al. The Ward: The Life and Loss of Toronto’s First Immigrant Neighbourhood. Coach House Books, 2015.

“The Man on Queen Street.” The Globe and Mail, 8 Jan. 1965, p. 7.

“Mayor Givens at the Helm.” The Toronto Daily Star, 26 Nov. 1963.

McHugh, Patricia, et al. Toronto Architecture: A City Guide. McClelland & Stewart, 2017.

McClelland, Michael, and Graeme Stewart. Concrete Toronto: A Guidebook to Concrete Architecture from the Fifties to the Seventies. Coach House, 2008.

Micallef, Shawn. “Toronto’s Mid-Century Sheraton Centre Is Modernism Worth Preserving.” Thestar.com, Toronto Star, 24 Jan. 2020, https://www.thestar.com/opinion/contributors/2020/01/24/torontos-mid-century-sheraton-centre-is-modernism-worth-preserving.html.

“Military Hospitals Report Submitted.” The Globe, 27 Oct. 1916, p. 8.

“New City Hall Judges Urge Redevelopment of Downtown Area.” The Globe and Mail, 15 May 1958, p. 29.

“New Russia Calls Sons.” The Toronto Daily Star, 2 June 1917, p. 5.

“Now in Their 70th Year, Featuring ‘Quality Value and Service’.” The Toronto Star, 27 Sept. 1979, p. B3.

“Pawnshop Is Held Up and Ottawa Clerk Is Seized by Police.” The Globe, 31 May 1928, p. 22.

“Police Spring Surprise: Fifty Chinamen at 113 Queen Street West Last Night.” The Toronto Daily Star, 9 Sept. 1904, p. 1.

“Political Parties At City Hall.” The Toronto Daily Star, 3 Dec. 1963, p. 6.

“A Program For Toronto.” The Globe and Mail, 25 Nov. 1958, p. 7.

“Progress Report: Queen Street Redevelopment.” The Globe and Mail, 10 Oct. 1960, p. 7.

Promiscuous Affections: 1971, http://www.rbebout.com/bar/1971.htm.

“Queen St. Hotel to Be Started next Week.” The Globe and Mail, 24 Apr. 1969, p. 5.

“Queen Street Expropriation Approved 17-4.” The Globe and Mail, 13 Aug. 1964, p. 5.

“Queen Street Plan: Will Build to Design Of 1963, Dennis Says.” The Globe and Mail, 9 Sept. 1965, p. 5.

“Queen Street Project: Municipal Board Head Won’t Reopen Hearings.” The Globe and Mail, 30 May 1967, p. 5.

“Ready to Pay $25,000 to Move Hotel.” The Globe, 13 Feb. 1914, p. 7.

“Report on the Conditions of Hotels in Toronto Sent to Liquor Board.” The Globe and Mail, 4 Feb. 1946, p. 3.

Ross, Andrew [@hoghee]. “Tweet Message.” Twitter, 16 Aug 2022 https://twitter.com/hoghee/status/1559639434554789888?s=20&t=GT0tG6pTd3ZA5qCfAWQD4Q.

Ross, Daniel. “Sex on Yonge: Examining the Decade When Yonge Street Was the City’s Sin Strip.” Spacing Toronto, 9 Mar. 2017, http://spacing.ca/toronto/2017/03/09/sex-yonge-examining-decade-yonge-street-citys-sin-strip/.

Ross, Daniel. The Heart of Toronto: Corporate Power, Civic Activism, and the Remaking of Downtown Yonge Street. UBC Press, 2022.

Sandilands, Catriona. Complicating Queer Space in Toronto: How the Development of Toronto’s LGBTQ2I Spaces Fits within Homonormative and Homonationalist Scripts. https://yorkspace.library.yorku.ca/xmlui/bitstream/handle/10315/34706/MESMP02750.pdf?sequence=2.

Scheinberg, Ellen. Email to Bob Georgiou, 12 Aug 2022.

Sears, Val. “The Commercial Slum Across From City Hall.” The Toronto Daily Star, 1 May 1964, p. 7.

Senter, James. “Metropolitan Toronto: A Look at the Future of the City Hall Area.” The Globe and Mail, 18 May 1962, p. 7.

Sismondo, Christine Alexandra. “Toronto the Gay: The Formation of a Queer Counterpublic in Public Drinking Spaces, 1947-1981.” YorkSpace Home, 28 May 2018, https://yorkspace.library.yorku.ca/xmlui/handle/10315/34509.

“South Side Story.” The Toronto Daily Star, 31 Oct. 1958.

“The South Side Story: A Tragedy.” The Toronto Daily Star, 2 May 1964, p. 6.

Taylor, Doug. “Toronto’s Broadway Theatre (Globe, Roxy) on Queen St. West.” Historic Toronto, 10 Jan. 2014, https://tayloronhistory.com/2014/01/09/torontos-old-movie-theatresthe-broadway-theatre-on-queen-st/.

Taylor, Doug. “Toronto’s Old Movie Theatres-The Infamous Casino on Queen St.” Historic Toronto, 6 Nov. 2013, https://tayloronhistory.com/2013/11/06/torontos-old-movie-theatresthe-infamous-casino-on-queen-st/.

“Too Soon To Cheer For Queen St.” The Toronto Daily Star, 27 June 1963.

“Urge Design Competition For Queen Street Project.” The Globe and Mail, 29 May 1965, p. 5.

“What’s Ahead? Voters Tell City Get on with Queen Development.” The Toronto Daily Star, 8 Dec. 1964.

The ‘Commercial Slum’ That Once Stood Across Toronto City Hall

Note: This article is the first piece in a two-part series. The second article can be found here.

When Toronto’s New City Hall and Square opened in 1965, there was a problem. While Ontario’s Capital was looking to move into a new era, the commercial strip across the new civic centre did not fit into those plans for modernization.

“Redevelopment Area” or “Commercial Slum”?

In 1958, Toronto was in the midst of an international design competition to construct a new city hall and square. The winning entry had not yet been chosen, but the jury — a panel of architects and town planners — had a particular recommendation. For the new landmark to be better situated, Toronto needed to redevelop the downtown area all around the site to better complement it, including the street directly opposing the civic centre. They proposed:

“City action to replace the unworthy buildings on Queen St., between Bay and York Sts., with a continuous facade, not over 90 feet high, with an open arcade under the building for the whole length.”
The Globe and Mail, May 15, 1958

The Globe and Mail agreed with the report of the jurors, citing “it would be a disgrace to leave a stick of it standing as a backdrop to the expensive – and, we hope, beautiful – Civic Square.”

In September, Toronto Planning Board was instructed by the Board of Control to make proposals on the Queen St. frontage. The board recommended the city buy the site and then sell or lease it to a developer. The Globe and Mail also called the south side “a hodge-podge of small, old buildings in various states of repair” and the shops “remain as reminders of that former area, bearing little relation to present surroundings.” The land was divided into separately owned lots and it was estimated $7,000,000 would be needed to buy them.

On October 27, 1958, the city passed a bylaw formally calling the strip a ‘redevelopment area’ and “giving the city expropriation powers over all but one of the properties.” The Toronto Daily Star was blunter in its characterization and advocacy of the fate of Queen Street West:

“Nearly everyone agrees that our handsome new city hall – when and if it is built – should not have to tolerate a commercial slum in front of it. And Queen St. between York and Bay is a tawdry hodge-podge”
Toronto Daily Star, October 31, 1958

The Daily Star and its editorial page in particular were very aggressive in their advocacy. It quite frequently enployed the phrase ‘commercial slum’ in the 1960s when reporting about the state of the site, including a December 1962 ‘Special Report’ boldly entitled “Our New City Hall Will Face a SLUM”:

“The rising towers of the new city hall look across Queen St. W. to a shabby vista of beer parlors, pawnshops, second-hand stores, a closed-down burlesque house.”
Toronto Daily Star, December 29, 1962

Still, the conservative outlet was interestingly weary of using public power to transfer property from private hands to private hands, i.e. the government moving shops from smaller, independent owners to larger, independent developers.

Whether the Queen Street row was euphemized as a ‘redevelopment area’ or disparaged as a ‘commercial slum’, urban renewal and slum clearance were certainly in the psyches and goals of governments of all levels in Canada and the United States of America for several decades in the 20th century. For Toronto, several lower-class neighbourhoods with ‘uneconomic uses’ were identified as requiring clearance and renewal. Regent Park became the first social housing project in Canada in 1947. The southern half of The Ward itself was voted to be expropriated in 1946 for the new city hall and square project, an area centred around Elizabeth Street once known as the first Chinatown in Toronto; the dense “slum” as a whole had calls to be rebuilt going back to the 1910s.

At work was the need to also rejuvenate Toronto’s historic downtown retail districts. Historian Daniel Ross wrote the city created its “pro-development Plan for Downtown Toronto” in 1963 with Yonge Street as a central part. After World War II, the rise of the automobile and urban sprawl impacted the central core, “emptying out” of its historical commercial districts as the suburbs developed their own retail and residential nexuses. A large part of the downtown plan was the Timothy Eaton Company’s Project Viking. First conceived in 1958, it was an endeavour which would reimagine the commercial empire’s ageing downtown holdings of mainly early 20th century warehouses as a post-war shopping centre. The project would become The Eaton Centre.

The Queen Street West Strip in History

In the early 20th century, the near three hundred-metre stretch of Queen between Bay and York Streets was characterized by hotels, restaurants, second-hand goods shops, barbers, butchers, jewelers, pawnbrokers, billiard shops, grocers, and fruit shops. Located on the southern edge of The Ward, a working-class immigrant enclave in the heart of Toronto, it also had East European Jewish and East Asian owned and ran-enterprises, such as restaurants, shops, and clubs.

First, the 1920 Toronto City Directory offers an interesting snapshot of the prominence and variety of Chinese businesses and organizations on the street. In this small zone, there were six Chinese restaurants (sadly all un-named as per the style of the directories in this period) and two tea-related businesses. Two organizations were on the street: The Chinese National League and The Chinese Reform Association. There was also a gentleman’s furnishings shop and possibly a photography shop. Yet Chong Lung Co. is referenced at 117 Queen, although it is unclear what type of dealings it entailed.

105 Queen Street West was a curious address in 1926. The city directory for the year divides the building into 105 — Tighe Lee, billiards — and 105 1/2 — Chinese National League. A picture from the year shows a sign above the door possibly reading “Pool Room”. The sign above that is written in Chinese with an illegible English caption underneath, roughly translating to “Kuomintang Office” or “Republic of Taiwan Political Party”. The smaller third sign on the third floor roughly translated to “World Mirror”, an arts society set up by the Kuomintang.

*105 Queen Street West, 1926.*
*Source: City of Toronto Archives*

113 Queen Street West was an intriguing case in that at different points it hosted a Chinese restaurant, the Jewish Daily Eagle, and the Union Ticket Office. In the 1910s, the address was listed in the city directories as hosting a Louis Gurofsky, Joseph Gurofsky, and Samuel Gurofsky at differing times. They were also characterized as ‘insurance agents’. By the 1920s, it was listed as The Union Ticket Office — a steamship ticket business.

Steamship ticket agents were common professions for Jewish-Torontonians and there were several competing businesses in The Ward. The enterprises played a role in the immigration process for Jews abroad. Historian Jack Lipinsky wrote “steamship agents, as their name indicates, originally concentrated on issuing boat and train ticks, mostly to immigrants.” Agents were landsmanschaften and “remittance agents” who worked with the Jewish Immigration Aid Services to bring Jews to Toronto. Lipinski notes that some agents were “dishonest” and defrauded prospective immigrants, including a David Gurofsky. It is unclear if this is the same or related Gurofsky(s) who operated at 113 Queen Street, but the damage done to the industry by him was enormous. The director of Canada’s Immigration Branch, Frederick Charles Blair, was “permanently suspicious” of the Jewish community because of Gurofsky’s dealings, a development which would later impact fleeing European Jews in the 1930s and 1940s.

The Gurofsky office seemed to play roles in the First World War. In 1916, the steamship office was responsible for enlisting “Hebrews”. The Globe reported it expected “at least fifty men” in Toronto to sign up for the great war and that over 1,100 had already joined across Canada. In 1917, Louis Gurofsky, at the delegation of the Russian consul, was tasked with “rounding up” prominent Russian Torontonians to return to their home country at the request of the new Russian Provisional Government who were “honeycombing” for “former friends — revolutionists and socialists” who had left Russia. Finally, The Daily Star reported in July 1917, a Mischa Bedler of 113 Queen Street West, a 24-year-old Jewish inventor handed over “a very valuable discovery in wireless telegraphy” to the Canadian government and was promoted to a lieutenant and instructor in the Royal Flying Corps.

Some of the businesses were mainstays on Queen Street for much of the 20th century. Simon Simonsky (occasionally spelt ‘Simonski’), a pawnbroker, was in business since at least the 1890s, settling at 121 Queen and then 107 Queen, where he would stay for at least sixty years. Historian Ellen Scheinberg wrote the family may have been peddlers originally: wandering street salesmen pushing carts of goods. A common professional trajectory of peddlers was to raise enough capital to open a shop, which Simonsky seemed to accomplish. According to a 1954 obituary for Mrs Annie Simonsky, the Simonskys were a “family long active in Jewish communal circles in Toronto”. By 1964, with forced closure looming, the shop moved to 115 York Street.

Harry Stein, a Russian watchmaker, landed on the Queen Street strip in 1932 at a shop at 63 Queen named Henry & Co (in the city directories, it was originally listed as ‘Harry Stein, jeweler’; the business also started as a watch repair shop on Yonge Street in 1909). In 1945, the jewelry business moved to 113 Queen — the former site of Gurofsky’s steamship ticket office. It later added other products and electronics to its offerings, most notably cameras, making it the first Henry’s, as we know it today. Henry’s later resurfaced at other locations, including 119 Church Street near Queen Street East in the 1970s. Henry’s announced in 2022 it would be leaving this location and a condominium is proposed to take its place.

Palaces of Sin

Two cinemas also were huge presences on the Queen Street row. The Broadway Theatre at 75 Queen Street West was on the strip since 1919, opening as the Globe Theatre. Historian Doug Taylor wrote the theatre started playing “‘Girlie Shows’ as well as vaudeville and B-movies”. In the 1930s, it was briefly the Roxy and changed to its final name in 1937. In 1935, the manager of Broadway was found murdered in his office; the killing was never solved.

The Casino Theatre at 87 Queen Street West was an “infamous” burlesque house built in 1936, according to Taylor. He pointedly described the movie house: “Throughout the theatre history of Toronto, other than perhaps the Victory Theatre on Spadina, there is no entertainment venue that has elicited as much praise, raunchy stories, condemnation and newspaper coverage as the infamous Casino Theatre.”

The theatre had reputable architects, Kaplan and Sprachman, who were famed for many of Toronto’s beautiful art deco theatres. The owners of The Casino partnered with the owner of the neighbouring Broadway to open the venture. But a foul reputation followed the Casino itself, which “was famous for its raunchy comedians and risqué burlesque” and “decent citizens” called a “sin palace”. In 1961, the Casino was renamed ‘the Festival Theatre’ as a failed attempt to clean up its image. In the final year of its existence, the theatre was playing a Russian Film Festival, perhaps as a means to that end.

Two hotels — the bar beer parlours referenced by the Star – were (in)famous on the south side of Queen. The Municipal Hotel stood at 67 Queen Street West since at least the late 1890s. The Municipal seemed to have a rowdy reputation throughout its history with fights, arrests, and fires plaguing its life. In 1946, Toronto Police prepared a report on hotels to send to the Ontario Liquor Board and had this to say about the hotel:

“Municipal Hotel, 67 Queen St. W.:

‘The chief complaint against this hotel is thefts from drunks who are permitted to become inebriated on the premises. It is also a rendezvous for prostitutes, and a number of girls have been removed from the premises by the police. This hotel is poorly managed and there is much room for improvement.'”
The Globe and Mail, February 4, 1946

Several doors down, at 71 Queen Street West, there were several versions of a hotel at this location since the early 1900s: the Aberdeen Hotel, Lennon’s Hotel, the White’s Hotel, and finally the Union Hotel/House. The Union had a similar seedy reputation to the Municipal. The 1946 report wrote:

“Union Hotel, 71 Queen St. W.:

‘This place appears nothing more than a pickup place for prostitutes, and it is amazing to find how many girls in the downtown area will give their address as the Union Hotel. Plainclothesmen have removed many girls from the premises, and only recently they arrested two teen-agers who had stayed at this hotel three nights with different men each night. A number of girls arrested in this hotel were found to have venereal disease. Improvement by the management in regard to the conduct of this hotel is long overdue.'”
The Globe and Mail, February 4, 1946

Interestingly, The Union and Municipal played notable roles in the history of Toronto’s gay community after World War II. Of the 1950s and 1960s, historian Christine Sismondo wrote the bar rooms of both hotels became places where the gay and lesbian communities were patrons, so much that the area around Queen and Bay was known to the groups for “cruising” as “The Corners” or “Queer Street”. The Municipal in particular was “known for its cheap beer by the glass and transient clientele” in this period and “received far more surveillance” than other establishments along higher class lines. It was known to be a “rough” bar, patronized by hustlers and ex-convicts.

Given this overall history and characterization, it is easily conceivable why the Queen Street frontage held such little value for Toronto decision-makers. Fire, assault, murder, sex, and more all found homes on the street. The shops and professions themselves were of inconsequential business value, the two theatres were ‘sinful’, and the hotels were cheap establishments with questionable management and clientele. Even including the impressively designed Broadway Theatre, the built form of the street was not of any notable architectural significance. Taken together, the row was simply expendable for a city looking for “progress”.

A Toronto intersection named for the same British royal

What’s the most colonial representation of colonial Toronto in Toronto? It might be a street marker built into the corner of a George Brown College buiding at Frederick Street and Adelaide Street East.

But the marker itself doesn’t read Frederick and Adelaide; rather, it reads Frederick and Duke. Frederick is still Frederick, but Duke doesn’t exist anyore.

The laughable part of this intersection is it was at one point named entirely for the same guy: Prince Frederick, The Duke of York of Great Britain.

At the time Duke and Frederick were named, the settlement containing them was also named for Duke Frederick: The Town of York. The Duke never visited the town named for him or likely had any direct role in its formation or growth. The British locales contained in his title also got a street name further west of the town – York Street. The Duke was also the son of King George, the reigning monarch at the time of the town’s founding, who had at least two other street names – King and George – named directly and indirectly for him.

And even more, nearly every street in early York was named by another Brit in charge of this colony: John Graves Simcoe, who didn’t like the indigenous name for the region — Tkaronto. Instead, when setting up his new town and the first few streets in it, he felt it more worthy honouring a man from his home country who scored a victory in his own continent as well as after other members of the British nobility and royalty.

The Town of York would revert to its indigenous name, albeit with an English spelling – Toronto. Duke Street would merge with and take on the name of the nearby rerouted Adelaide Street, named for another royal who likely didn’t have any contributions to the city either.

As a layered bonus, this wasn’t even the first time Duke Street was involved in a name change. The original Duke Street was today’s King Street. The original King Street was Palace Street, today’s Front Street. The Duke Street before this northern re-shifting was Duchess Street, named for the Duke’s royal counterpart. Duchess would move up a street too. It also merged with and took on the name of nearby Richmond Street. The streets of the original blocks of Toronto clearly had a colonial theme.

But today, the marker at Frederick and Adelaide Street still reads Frederick and Duke, still honouring the same guy.

Two Amazing Rooftop Views of Toronto’s The Ward

In the early 1900s, St. John’s Ward or familiarly just ‘The Ward’ was a dense, immigrant enclave in the central core of the City of Toronto. The neighbourhood was roughly bound by Queen Street, College Street, Yonge Street, and University Avenue, and housed some of the city’s first Black, Jewish, Chinese, Irish, and Italian colonies. Two early 20th-century rooftop photos provide interesting overhead views of the physical makeup of the district.

The first rooftop view was taken in 1920 by iconic Toronto photographer William James from the top of the Alexandra Palace Apartments, formerly located at 184 University Avenue opposite the terminus of Gerrard Street West on the edge of The Ward.

The southeasterly scene below and far beyond the Alexandra Palace Apartments is fascinating. In the foreground is a great visualization of University Avenue’s history as two separate streets. Among the recognizable landmarks are Old City Hall and the T. Eaton Co. factory complex in the background (more on this further down), the Hester How School at centre-left, the Presto-O-Lite factory and the Toronto House of Industry at centre, and the African Methodist Episcopal Church, First Baptist Church, and Maclean Publishing Co factories at centre-right. Interspersed is a dense grid of low-rise housing and other structures which ultimately came to define The Ward.

There was another photograph also taken by James from the Alexandra Apartments, this one dated to “circa 1920”. Although generally quite similar, noticeable differences exist between this and the 1920 photo, most visibly that the latter is a much broader view of the same general area of The Ward.

While the date of the zoomed-in image is approximate, it almost certainly precedes 1920. The main differences between this and the 1920 photo is the lack of the Prest-O-Lite Factory (built 1917) and the northernmost Eaton’s factories (also built 1917). The most important detail, however, is the Eaton’s Annex building, which appears under construction. The store opened in 1913, which likely dates the image to 1912 or 1913.

The Alexandra Palace Apartments (also simply called the ‘Alexandra Apartments’, ‘The Alexandra Palace’, or ‘The Palace’) was a 7-storey, luxury apartment building constructed in 1904 during Toronto’s first apartment building boom, meaning it was one of the first of its kind in the city. The architect was the prolific George W. Gouinlock, who also designed the Temple Building. Famous residents included tycoon E.P. Taylor and Ontario Hydro founder Sir Adam Beck (the old Ontario Hydro Headquarters was directly north of the apartment). It is said that residents moved into the Palace to retire.

In the 1920s, the Palace went from apartment house to apartment hotel with a dining room already in its offerings. In the 1940s, the building was slated to become a nurses’ residence for Sick Children’s Hospital. By the 1950s, the building ceased to be a residence and was heavily remodelled to be a modern office building, losing much of its original exterior features. In 1968, the Alexandra Apartments building was demolished.

Postcard of The Alexandra, Queen’s Park Avenue, Toronto, Canada’s Finest Apartment House, 1910. Source: Toronto Public Library.

Postcard views of the Alexandra Palace, 1910s. Credit: Chuckman’s Photos.

The second rooftop photograph comes from the top of an Eaton’s factory tower once located adjacent to the Church of the Holy Trinity. Like the Alexandra Apartments picture, it was taken by William James. It is dated “circa 1910.”

The view is looking northwesterly over The Ward and has several common landmarks with the 1920 Alexandra Apartments image, such as Toronto House of Industry, the Hester How School, and the Grace Church. In the foreground along Bay Street (at the time called Terauley Street) and Dundas Street (Agnes Street) are the Terauley Street Synagogue, the Lyric Yiddish Theatre, and Police Station #2 (which appears to have officers in its yard). As with The Palace image, there are also the tightly packed streets of tiny residences, many undoubtedly housing men and women who were employed by Eaton’s. Finally, the distinctive rooflines of Queen’s Park and Toronto General Hospital loom far in the distance (with the Alexandra Apartments somewhere nearby).

The Eaton’s factory itself where James captured the image was a 12-storey structure located adjacent to the Church of The Holy Trinity. It was built around 1910 in a period when the Eaton’s footprint in the area expanded from a single store at 190 Yonge Street in 1883 to encompass at least half the block between Yonge, Bay, Queen and Dundas Streets by 1920. The factory was demolished in the 1970s when other Eaton’s factories and warehouses were razed in part to make way for the Eaton Centre (The Eaton’s Annex store referenced earlier was destroyed by fire in 1977).

The Eaton’s image is dated “circa 1910”, which is likely accurate as it is very comparable to the “circa 1920, but likely 1912-3” Alexandra Apartments photo. The Prest-O-Lite factory does not appear in the image, thus 1910-1917 is a fair timeframe.

Today, if the two William James rooftop photos were recreated, they would be taken from Mount Sanai Hospital and the Bell Trinity Square office building, respectively. Ironically, the Alexandra Apartments and the Eaton’s factory were both constructed and demolished in similar periods: the 1900s to 1910s and 1960s to 1970s. The dwellings, houses of worship, and businesses of The Ward also largely disappeared by the 1950s as lands were expropriated for various projects. The district continued to change since then until the present-day, making these century-old views a far cry to today’s world.

Category: Downtown