A Quick History of Winchester (Royal) Drive, Toronto

On September 14, 1878, The Globe reported on “The Great Rainstorm”, a phenomenon that overwhelmed Toronto and the Don River. A view from the Necropolis Bridge, the crossing near the cemetery, described the water swelling gradually in the morning, but overflowing by eight o’clock. By mid-day the bridge had been completely swept away. The river was a wild scene of flowing water and debris. Fortunately, the newspaper reported a week later that the bridge was re-erected and travel was resumed. The dramatic event is one episode in the life of the bridge and road, which would come to be a notable, lost part of Toronto’s history and geography.

The Winchester Street Bridge

The crossing at Winchester Street and the Don River was an important one in and out of the City of Toronto. And potentially one of the oldest. A bridge has existed in some form since the days of John Graves and Elizabeth Simcoe. That latter wrote in her journal of “Playter’s Bridge,” a crossing made of a fallen butternut tree. Later versions of the bridge included sturdier constructions, albeit were prone to washouts as per the 1878 storm and another storm in 1894, which resulted in its “almost complete destruction.” They were also variously named: The Necropolis bridge as mentioned, the Winchester Street bridge which was the most common name, and simply the Don Bridge (albeit this was more famous as the crossing at today’s Queen Street).

In a pre-Bloor Viaduct Toronto, the Winchester Street Bridge and the road extending from it was the most northern path to and from the city on the east side. Its origins lay in the 1840s, likely as an alternative to the Queen Street bridge for travelers heading into market. Its location at this junction points to its prominence as a stop on the way into and out of town — and an ideal spot for a tavern. The Don Vale House stood on the west side of the Don River near the bridge from the late 1840s. It was noted as a popular yet rowdy locale, particularly for gambling activities. It was torn down in 1876. There was also an old toll-gate house which “stood for so many years at the foot of the hill close to Winchester Bridge,” which was removed in 1882. It was reported as an “eyesore” and “tramps who have lodged there free of cost will miss the old shanty.”

Over its history, numerous repairs have been made to the Winchester Street bridge, including rebuilding it altogether. In addition to a new causeway built after the 1878 storm, it was reported in October 1885 that the “new Winchester-Street bridge” was almost ready; it was already planked, and the approaches were just about complete. In late 1888, the idea of erecting a high-level bridge was being explored. In 1894, the bridge was described as “long been regarded as unsuitable and unsafe during floods,” as proven by the storm that decimated the bridge that year. In 1902, a proposal was endorsed to fit the bridge with $10,000 of lumber to repair the bridge. In March 1909, the bridge was condemned and majorly repaired and rebuilt at a cost of $15,000. It was reported that during this time, travelers on the Danforth would have to use the Gerrard Street bridge as an alternative until the bridge opened several months later. This somewhat regular need to repair or rebuild the bridge might reflect its frequency of use and its proneness to disaster caused by the Don River.

Here The Road Winds…

The winding road on the east side of the bridge was curiously not also named Winchester Street. Rather, it took on several monikers throughout its history. It must be noted that it is not easy to track the changes as its naming in maps and directories does not appear to be consistent — that is, sometimes it is not named at all or concurrent sources will name it differently. The first names identified in the 1800s seem to have been the similarly related Don Road, Don and Danforth Road, and Don Mills Road. After the turn of the century, it took on Winchester Drive (or Road), which is likely its most famous name. Its final evolution was as Royal Drive.

It must also be noted that Winchester Drive was related in name and geography to the modern Broadview Avenue, but that connection and timeline is somewhat murky. An old aboriginal route lent itself to a new road in 1799, running east from the Don Bridge at Queen Street northwards to the saw and grist mills on the Don at about Pottery Road. It would aptly be named “The Mill Road”. In an 1884 annexation, The Mill Road was split in name north and south of Danforth Avenue into Don Mills Road and Broadview Avenue, respectively, possibly reflecting the odd, angular path taken by modern Broadview as it crosses Danforth Avenue.

However, in somewhat conflicting evidence, the 1856 Directory splits the two roads into The Mill Road, from Queen Street to Danforth Avenue, and The Don (and Danforth) Road, from Winchester Street to north of Danforth into Todmorden. This meant that for a time, the road leading northeast from the Winchester Street bridge and the road northeast of The Danforth was the same continuous road, even if their origins may not reflect that. Both roads were named Don Mills for a time as well.

Winchester Drive would run along the river before turning east to pass under the Canadian Pacific Railway subway (appropriated also called the Winchester Street subway). In 1918, a flood caused by an ice-filled Don River made the road impassable, pointing to the low-lying situation of the southern part of the street. As it curled northeastward, it was positioned between two ridges, with Broadview Avenue overlooking on the east side. This followed the topography of the former Dallimore Creek, a tiny Don River tributary. At the top of the hill was the Taylor Tollgate, which was situated on the south side of Danforth Avenue in the corner between Winchester and Broadview Avenue.

In 1901, the Swiss Cottage Hospital for smallpox was built on the west side of Winchester Drive. The isolation hospital was formerly located near the Don Jail and moved to a more remote area north of Riverdale Park when life around Gerrard Street grew busier. Winchester Drive had very few dwellings on it — if any at all. The Globe reported on its opening:

Constructed for its estimated cost, $5000, it is a picturesque structure of brick and stone, in the Swiss style of architecture. Bosomed in the precipitous cliffs that overlook the eastern banks of the Don, it is ideally situated. Looked at from the river flats it occupies a commanding height, yet behind and beside it to a height of 40 feet above it rise the steep banks of the Don. Taylor’s road winds up the cliffs just south of the hospital, but separated from it by a deep ravine. The hospital is practically in the centre of 150 acres of natural park land, and far from habitations.
The Globe, November 27, 1901

In 1927, it was reported that the hospital would close as it was deemed inadequate to deal with recent smallpox epidemics. The Swiss Cottage stood until 1930 after facing its unfortunate end by fire.

The Royal Drive

Winchester Drive took on its final life in 1939. It was renamed Royal Drive to coincide with a visit by King George VI and Queen Elizabeth. Their motorcade traveled down the road into Riverdale Park for a demonstration by schoolchildren. Royal Drive would be used again in a similar manner in a subsequent royal tour in 1951 by Princess Elizabeth and the Duke of Edinburgh. It was reported at the time that the street would need to be completely resurfaced as it was covered in potholes. Princess Margaret traveled down the street in 1958, the last time a British Royal would do so.

Royal Drive met its end via the Don Valley Parkway project in the late 1950s. On the west bank of the river, the road descending down from The Necropolis was removed near the river to make way for the Bayview Extension. Today, Winchester Street ends at the top of the hill near Riverdale Farm and the cemetery. The Bayview Extension also necessitated the removal of the now-orphaned Winchester Street Bridge.

The Globe and Mail, ; May 8, 1959.
Source: Globe and Mail Archives

On the east bank of the river, the roadbed for Royal Drive was also removed and replaced at its north terminus by an onramp to the northbound Don Valley Parkway. Eastbound travelers on the Bloor Viaduct might note that a sign for Royal Drive hangs over the entrance to the ramp. According to the City of Toronto, this marker does name the highway entrance as Royal Drive. Interestingly, however, Royal Drive does not appear on the city’s Road Classification List as a street.

To compound the issue, a trail running on the table of land adjacent to it and the former Danforth Lavatory and City Adult Learning Centre is marked on Google Maps as Royal Drive. This path continues down into the valley, crossing over the onramp via a bridge and continuing into Riverdale Park.

Whichever is the case of the “real” Royal Drive, the lack of complete erasure of the name is likely intended to honour the royal tours of the past decades. It also aids in keeping alive the history of an early and prominent Toronto street.

Sources Consulted

Attachment No. 4 Historical Chronology – City of Toronto, http://www.toronto.ca/legdocs/mmis/2015/pb/bgrd/backgroundfile-85136.pdf. Accessed 24 Mar. 2024.

“Avenue Road Extension.” The Globe, 27 Sept. 1902, p. 22.

Axon, Elizabeth. “Some Memories of Old Don Mills Road.” The Globe and Mail, 4 June 1955, p. 19.

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

“Bridge Condemned.” The Globe, 18 Mar. 1909, p. 4.

Cabbagetown Uncovered: The Story of Toronto Can Be Found by Following …, http://www.toronto.com/news-story/6442876-cabbagetown-uncovered-the-story-of-toronto-can-be-found-by-following-the-don-river-and-its-history/. Accessed 24 Mar. 2024.

“City Council Yesterday.” The Globe and Mail, 3 Oct. 1939, p. 5.

“City News.” The Globe, 2 Feb. 1882, p. 10.

“City News.” The Globe, 21 Sept. 1878, p. 8.

City of Toronto. “An Infectious Idea: Hospitals and Ambulance Services.” City of Toronto, 24 Nov. 2017, http://www.toronto.ca/explore-enjoy/history-art-culture/online-exhibits/web-exhibits/web-exhibits-local-government/an-infectious-idea-125-years-of-public-health-in-toronto/an-infectious-idea-hospitals-and-ambulance-services/.

“City to Spend $40,000 Primping for Royal Visit.” The Globe and Mail, 12 Sept. 1951, p. 4.

Davetill. “1951 Royal Visit.” Toronto Old News, 13 Oct. 2020, torontooldnews.wordpress.com/2020/10/12/1951-royal-visit/.

“Debris Strewn in Don Valley.” The Globe, 27 Feb. 1918, p. 11.

“Don Vale House.” Don River Valley Historical Mapping Project, maps.library.utoronto.ca/dvhmp/don-vale-house.html. Accessed 23 Mar. 2024.

“The Earth Trembled.” The Globe, 1 Apr. 1896, p. 12.

“Gerrard Street Bridge.” The Globe, 15 Nov. 1878, p. 2.

“The Great Rainstorm.” The Globe, 14 Sept. 1878, p. 8.

Lambert, FW. “‘Don Mills’ Disappears.” The Globe, 3 Sept. 1938, p. 6.

Limeback, Rudy. Rediscovering Royal Drive, rudy.ca/rediscovering-royal-drive.html. Accessed 23 Mar. 2024.

“Municipal Items.” The Globe, 24 Dec. 1888, p. 3.

“Must Raise The Money.” The Globe, 13 May 1909, p. 7.

“New Smallpox Hospital.” The Globe, 27 Nov. 1901, p. 9.

“Notes.” The Globe, 5 Apr. 1894, p. 5.

“Old Swiss Cottage May Be Closed Soon.” The Globe, 16 Dec. 1927, p. 14.

“Public Notice.” The Globe and Mail, 10 July 1958, p. 10.

The Ravines Reach of the Don River, http://www.lostrivers.ca/content/Ravinesreach.html. Accessed 23 Mar. 2024.

Robertson, John Ross. “Don Vale House, c. 1870.” YorkSpace, Landmarks of Canada, 1 Jan. 1870, yorkspace.library.yorku.ca/items/f56c0b9e-17c5-406d-a89d-c64eb9cd7b23.

“Royal Drive.” The Globe and Mail, 8 May 1959, p. 13.

“Royal Procession.” The Toronto Daily Star, 11 Mar. 1939, p. 1.

SCADDING, HENRY. Toronto of Old. OUTLOOK VERLAG, 2020.

“A Tavern Stand to Be Let or Sold.” The Globe, 6 Apr. 1858, p. 3.

The Tollkeepers Cottage and Early Roads, http://www.lostrivers.ca/content/points/earlyrds.html#dmr. Accessed 23 Mar. 2024.

“Winchester Street Bridge.” The Globe, 24 Nov. 1885, p. 10.

A geographic history of a North York neighbourhood

Note: This article is written without any prior affiliation to or contextual knowledge of the history of the Highland Memory Gardens or the family farms of North York. Their inclusion is as a reference tool to show change.

This is Highland Memory Gardens. It is located near the intersection of Don Mills and Steeles Avenues, in Toronto’s north end. The development of this cemetery and its surrounding area is an interesting look into the creation and evolution of this inner suburbs.

This is the area around Highland Memory Gardens in 1860. Historically, the area consisted of lot 21 (at today’s Finch Avenue) to lot 25 (at Steeles Avenue) of the Third Concession East of Yonge Street (Leslie Street), which were generally 200-acre lots extending to the Fourth Concession East (Woodbine Avenue/Highway 404). Notably absent is a middle road (now Don Mills Road) between the two concession roads. The cemetery itself is located along the east side of the top half lot 23 and the bottom half of lot 24.

As seen this 1878 map, the area was part of the larger community of L’Amoreaux (also spelled L’Amaroux). The village crossed both sides of the North York-Scaborough townline, with its spine running along Finch Avenue and lots extending to Steeles and Sheppard Avenue.

The L’Amoreaux Post Office stood just west of Victoria Park Avenue on the south side of a lost section of Finch Avenue (it would be re-aligned through the townline in the 1970s). Further west, a Methodist Church and cemetery, a Temperance Hall, and School House stood near Leslie Street.

Cutting diagonally through the large block was a creek, now named Duncan Creek. It ran from near Leslie and Steeles (where its namesake’s farming lots stood) to its terminus near Victoria Park and Finch. It does not to seem to have been a major source of industry, compared to the adjacent Don River which hosted a number of mills. In the 1916 map below, the creek slinks its away across lots, although its course is a bit off compared to the earlier maps and later aerial photographs.

This 1954 aerial photograph is a visual of the area and tells us that even by this decade, the area still maintained its largely rural character. A more precise view of the creek is visible along with the greenery running along its course.

For the area plot that would become the Highland Memory Gardens, 1953 was last year it existed as farm fields. A key reference point is the small roadway leading from Woodbine Avenue to a farm near the banks of Duncan Creek. This roadway was the divisor between lots 23 and 24.

The cemetery found a home to the west of Woodbine Avenue, with an entrance leading off the street. The initial layout of the cemetery is a circular path. Some “offshooting” paths seem to laid out as well.

By 1956, an “arm” shoots off the southern half of the main circle, looping west to connect to the main roadway.

By the close of the decade, the layout of the cemetery increased more with off shoots on the north of the main circle.

In 1962, more acreage is added westward and a pond on the north east corner of the plot seems to be more completed. The lawns of the ground look to be landscaped. A tiny building, potentially the administrative centre, appears at the top of the lot.

The midpoint of the decade saw few geographic changes, but the notable start of residential development to the west of the creek.

By 1968, the cemetery expands again to the west. It would be its last major territorial expansion. The subdivision to the west of the creek appears complete, clearly stopping at the property line midway between Woodbine and Leslie.

By the start of the 1970s, development starts to grow to the south of the cemetery, replacing the longtime farm buildings. An early Don Mills Road begins to curl in from the the south as well as an early McNiccol Avenue slinks from west to east.

By 1973, the farm buildings near the creek are razed as the land is about to be filled in by housing. The creek itself disappears under the subdivision to the south of the cemetery. The land north of the cemetery also sees new subdivisions.

By 1976, Don Mills Road is completed, seemingly bending through the area to provide a second access point to the cemetery. Townhouses are built between the creek and Don Mills Road.

By the 1980s, Highland Memory Gardens took on the form seen today. Highway 404 was completed in the late 1970s replacing the former Woodbine Avenue right of way. With that, the main entrance to the cemetery shifted to Don Mills Road with the old entrance off Woodbine being built over. Several other buildings would later fill the northeast corner.

Today, Highland Memory Gardens is part of the Hillcrest Village neighbourhood of Toronto, an area roughly encompassed by Steeles Avenue, Finch Avenue, Leslie Street, and Victoria Park Avenue.

The Zion Church and Schoolhouse still stand today as 19th century reminders, but references to the area as L’Amoreaux are non-existent today. The post office and its street are gone, with the Old Finch Avenue closed in 1977 and Pawnee Avenue roughly replacing it as the two Finches were connected. (The L’Amoreaux name does live on in Scarborough, of course.)

There is a trail and parkland which follows Duncan Creek; the Seneca Newnham Campus, founded in the late 1960s, now runs over a buried portion of the creek. The property lines of the 40-acre Highland Memory Gardens reference the old concession lots, offering a forgotten link to the past.

Scenes From Pape Avenue (East York)

Where does Toronto end and East York begin? On Pape Avenue, it’s a row of Edwardian houses half way between Selkirk Street and Aldwych Avenue. When they were constructed around 1914, Aldwych was named Randolph — a point highlighting the obvious British origins of the area and the evolution.

The history of the rough half-trapezoid between The Danforth, Donlands Avenue, and the Don River goes back to the numbered plots of York Township, which was surveyed and divided beginning in 1791. Lot 11 south of modern-day Browning Avenue and west of Logan Avenue encompassed the community of Chester (also interchangeably known as Doncaster).

Doncaster and Todmordern from the 1878 Illustrated Historical Atlas of the County of York. Credit: Old Toronto Maps.

North of Browning Avenue and west of Donlands Avenue (renamed from Leslie Street around 1916), the Taylors and Helliwells owned lots 12 to 15, which came to be known as the village of Todmorden, named after the families’ paper mill on the Don River on Pottery Road. A nexus of buildings including a post office and hotel sprang up on Broadview Avenue, then named Don Mills Road (more on this later).

Map of the City of Toronto showing wards and tax collectors divisions, 1893. Credit: City of Toronto Archives.

Pape Avenue and Bee (Cosburn) Street, Todmorden Mills, 1911. Credit: City of Toronto Archives.

According to Elizabeth Gillan Muir, author of Riverdale: East of the Don, Chester and Todmorden applied to be part of Toronto in 1890, but were collectively short of the 750 required for annexation (which gives one an insight to their size). Chester would eventually be brought into the big city’s borders in 1909.

Map of Township of York and City of Toronto, ca. 1909. Credit: City of Toronto Archives.

For the residents of Todmorden, they voted to incorporate into the Township of East York in 1922 at a time when the Pape Avenue strip began to grow. The opening of the Prince Edward Viaduct in 1918 along with the East York-Leaside Viaduct (now the Millwood Road Bridge) in 1927 opened the area to modern houses and commercial development. The East York bus line began operation on Pape in the same year, departing from Danforth Avenue up the street and looping back at the top of the bridge. In 1928, it combined with the Leaside bus, extending service into the industrial suburb. By the end of the decade, the street grid, once open fields, gave way to the modern layout.

Construction of the Leaside Bridge, 1927. Credit: City of Toronto Archives.

The Todmorden section of the 1920 edition of the Might’s Greater Toronto city directory offers an insight into the geography and social makeup of this initial period. Area residents, mostly of Anglo-Saxon origin, lived on recognizable streets, such as Woodville, Gamble, and Torrens. However, some roads changed names: Leslie to Donlands, Cronyn to Sammon (sometimes spelled ‘Salmon’), and Gardeners (named after the merchants on the street) to Mortimer, and Bee absorbing into Cosburn. Professions were mostly blue-collar and ranged from employment at the nearby Don Valley Brick Works and Don Valley Paper Mill, to the booming T. Eaton Co. and R. Simpson Co., to the mighty Grand Trunk Railway and Canadian National Railway.

City of Toronto Directory showing Todmorden, 1920. Of note are the members listed under one household and their varying professions, like the Boyes. Credit: Toronto Public Library.

Moving around Pape from Browning to O’Connor, one sees signs of the age, look, and evolution of the old neighbourhood from the first half of the 20th century. At Mortimer, there isn’t a heritage building, but a plaque at Agnes Macphail Square points to the one-time existence of the Kitchener Public School. The school was a three-storey structure of seventeen rooms built in 1915.

Toronto Teacher’s College, 1965. Credit: City of Toronto Archives.

Kitchener School became the Toronto Normal School in 1941, moving from its downtown location on the current Ryerson University campus to Pape Avenue. After that, it was the Toronto Teachers College. Today Centennial College, the park, and a housing complex occupy the space. Macphail Avenue and Square themselves commemorate Agnes Macphail, the first woman elected to the Canadian House of Commons in 1921 and a former Member of Parliament for and resident of East York.

Another school, the Todmorden New School, opened a year prior on Torrens Avenue. It was renamed the William Burgess School in 1922; Burgess was a trustee in 1914.

At Cosburn, another institution – the Bethany Baptist Church – was constructed in 1920. The lot to the north of the church remained empty until the late 1950s, when an addition was completed on the space.

At 873-877 Pape Avenue, there’s a ‘1930’ displayed high above a block of shops. At the time of construction, the corner unit (now a Greek restaurant) was a fruit grocery operated by an Antonio Ruta — Italian in origin by the sounds of it — which represented an important shift in the otherwise largely British neighbourhood at the time and a larger trend in Toronto.

At 1007 Pape Avenue, north of Floyd Avenue, the flooring store currently standing was originally a confectionery by a James Hackin when it came to exist in 1930 (albeit at street address 1005). Interestingly, to the south of it was the ‘East York Miniature Golf Course’.

From Might`s Greater Toronto city directory, 1931. Although their street numbers have changed as well, 913 and 965 remain as a garage and corner store respectively in 2018. Credit: Toronto Public Library.

At 1016 & 1016 1/2 Pape Avenue is a curiosity. The icon above the shop appears to show a ship. A look into the city directories shows this block was built around 1931 when another Italian, Charles Azzarello, opened up a fruit grocery. By 1950, it was Sydney Evans Fish Market. In the 1960s, it came full circle as a ‘Circle Fruits’ and ‘Woman’s Bakery’. Sources are scarce on the ship emblem, although one might attribute it to its fish shop period.

Finally, Don Mills United Church looks down at the strip and is the oldest landmark of all, reaching back to the 19th century — even if the current structure dates to 1950. The adjoined Taylor Cemetery is the final resting place of early pioneering Todmorden families and is neat way to explore its history.

The naming of the church refers to the area’s mills and the street itself around its founding in 1851. Don Mills or just Mills Road originally ran northeast from the Winchester Bridge in Cabbagetown past Danforth Avenue, and turning right just past modern Woodville Avenue at what was then called Patterson’s Corners. From here, it would veer north just past Donlands across the Don River, following a course north to York Mills (it was extended even further in the 1960s.) A smaller section of Don Mills also continued east past the bend, stopping at present day Derwyn Avenue. From here, Plains Road (also called Globe Road) operated south and then east again. The Taylors also had a private right of way in line with Don Mills Road.

Don Mills Road, Plains Road, & Taylor’s Private Road, Goads 1924. Credit: Old Toronto Maps.

Broadview Avenue, first running north from Riverdale Park East (creating the ‘broad view’ of the Toronto skyline) to Danforth Avenue, was extended first to the city limits at Fulton Avenue and then to Patterson’s Corners. In 1929, John H. Taylor proposed the extension of St. Clair Avenue through his property in the Don Valley in exchange for a strip of land owned by The Synod of Toronto to make his private road into a ‘highway’ to connect with Woodbine Avenue.

“St. Clair Extension Through East York Offer of J.H. Taylor,” The Globe, January 21, 1929. Credit: Toronto Public Library.

Whether it was related to Taylor’s wish or not (for what it’s worth, St. Clair was never extended through the valley), the street was indeed completed to Woodbine Avenue in the following decade. In 1936, O’Connor Drive came into existence east of Don Mills Road facilitating an east-west route to the newly built Woodbine Bridge and Scarborough. By 1939, O’Connor would usurp the entire way from Broadview with development along the road growing in the 1940s.

Don Mills Road & O’Connor Drive from Might’s City Directory in 1935, 1936, & 1939. Credit: Toronto Public Library.

After World War II, Canada and Toronto saw a wave of unskilled and semi-skilled Greek migrants leave their homelands for new lives across the ocean. To be sure, Hellenes had been successful restaurateurs along Yonge and Queen Streets since the 1920s, but as Jason Hackworth and Josephine Rekers identify in their paper “Ethnic Identity, Place Marketing, and Gentrification in Toronto,” this new wave would settle around The Danforth beginning in the 1950s and ’60s and peaking in the 1970s. Like their Italian predecessors thirty years prior, they opened up fruit shops and eateries as new businesses or simply took over existing enterprises. Although their studies do not include Pape Avenue, one can see similar trends for the street. Hackworth and Rekers also assert that while the residential Greek population around the Danforth has decreased since the 1970s because of out-migration to the suburbs, the percentage of businesses with Greek affiliation has increased.

988-990 Pape Avenue in 1955 & 1965. The asterisks notes the owner of the building. Credit: Toronto Public Library.

Also in the 1960s, Cosburn Avenue east and west of Pape saw the introduction of apartment tower-tiving, replacing and mixing in with the post-war one-story housing stock dotted over the neighbourhood.

East York, 1965. A row of apartment towers centred on Cosburn begins to form. Business at the time were Dad’s Cookies at 940 Pape and Weston Bakeries at 1070 Pape Avenue. Credit: City of Toronto Archives.

Old and new in East York, 1966. Credit: Toronto Public Library.

In 1986, a new label — the Pape Village Business Improvement Area (BIA) or just ‘Pape Village’ — came into use. The BIA manages and promotes the commercial properties from Mortimer to Gamble, engaging in street improvement initiatives and an annual street festival. Today, the strip is an ecclectic mix of service stations and garages, mid-century houses, churches, and independent businesses and associations. Much of these still have a Greek affiliation, although the area is much more cosmopolitan with a variety ethnic eateries.

Useful Links

Historicist: Greektown on the Danforth

Jason Hackworth and Josephine Rekers – “Ethnic Identity, Place Marketing, and Gentrification in Toronto”

Toronto Normal School, 1847-1947

Toronto Public Library – Digital Toronto City Directories

Ward 29 Bikes & The East York Historical Society – “East York History Bike Ride”

Scenes From The Peanut, Parkway Forest, and Graydon Hall

When I was first told about a place in Toronto called the Peanut, I laughed. The Peanut? What kind of name is that? I was then explained that it really looks like a peanut.

Peanut Aerial Looking South Late 1960s — The Peanut Aerial Looking South, Late 1960s. Source: ERA Architects

But even after being told that and looking it up on a map, I still had no visual conception of it. Don Mills and Sheppard itself isn’t completely unfamiliar to me – I’ve known it since my childhood as the home of Fairview Mall. My family doctor is also located here. But Don Mills heading north toward Finch – no clue.

The peanut is the nickname given a development of high-rises and townhouses along Don Mills Rd. - because of the shape of the road in it when seen from the air. Most of it has been built in the past 10 years. Ratepayer groups say the high density of population has aggravated social problems. Two groups oppose a proposed condominium development nearby but other people say development is inevitable and developer should be asked what he would provide for recreation. — The Peanut Aerial Looking South, 1976. Source: Getty Images.

And thus, I begin at the top. Van Horne Avenue. To the north, the street consists of lanes of north-south traffic. To the south, the street splits off into singular direction-flowing lanes on either side of a giant curving island.

It’s not an original thought to suggest The Peanut isn’t very pedestrian friendly – even now, getting to its centre is unusual. A Walkability Study by Paul M. Hess and Jane Farrow goes into great detail about the issues – good and bad – about living and walking the Peanut. But even without defined criteria, one can see with one’s own eyes – and feet – how awkward traversing the Peanut can be. Walking toward the mall, I can already see someone jaywalking the southbound curve.

Peanut Plaza displays no obvious charm, but seems to hold a bit of meaning to the people that know it. Aesthetically, it’s clearly of another era: the mid-1960s, much like the rest of its surroundings. (The skylight inside, though, is commendable.)

It’s notably anchored by Tone Tai Supermarket, but every bit of positive word of mouth I’ve heard about the Plaza lies in its eateries – specifically Allan’s Bakery and Mr. Jerk, which have been described to me as having the best Jamaican patties and food in the city. Imagine that: such an unsung landmark in suburbia with some of the best food in Toronto.

The rest of the Peanut houses Georges Vanier Secondary School and Woodbine Junior High School. The latter is notable to me (and perhaps only to me) for its naming. Woodbine Avenue currently exists as two main stretches – one running south of the River Don and one running north of Steeles. The portion in Markham once extended south to the 401 and beyond. It was replaced by Highway 404 in 1976.

Peanut Woodbine DVP Aerial 1966 — Aerial of The Peanut & Parkway Forest, 1966. Woodbine Avenue and the Don Valley Parkway on the right. Source: City of Toronto Archives.

Created in 1963, The Peanut is the embodiment of post-war suburbia in Toronto: car designed streets, apartment buildings, strip malls, and minimalist looking schools.

I don’t venture into the residential streets, but in his exploration of the Peanut and the larger Don Valley Village, The Toronto Neighbourhood Walks Project‘s Jason points out the side streets add a new twist to the cookie cutter subdivision. Instead of the same house repeated over and over, it’s the same four in a row, creating a false sense of diversity. (As the comments point out, though, even the residents know this and are trying to instill some individuality to their homesteads.)

Peanut Aerial Looking Northeast Late 1960s — Peanut Aerial Looking Northeast, Late 1960s. Source: Vintage Toronto.

Don Mills West and East converge at Fairview Mall Drive, which houses Fairview Library and Theatre. For the longest time, I knew it as a great library branch – and an architectural slab of grey concrete. In 2013, a glass addition was added to its 1972 exterior. Only months after reopening, though, a flood shut down the library again.

Fairview Library 1976 — Fairview Library, 1976. Source: Toronto Public Library.

Across the parking lot is Fairview Mall. It was opened here atop farmland in 1970. Its anchors at the time were Simpson’s and The Bay. I think it might be the only major Toronto shopping centre that never had an Eaton’s.

It has grown a bit since my childhood; the tenants are different, the food court’s moved, and there’s no more Rainbow Cinemas and their cheap matinee movies. Even the parking lot is different. There are now fences separating the mall from the library and medical building lots.

Walking south to Sheppard Avenue, you have to be a mindful pedestrian. There are cars turning in and out of the mall as well as buses turning into the station.

There is a neat find in a plaque devoted to Northern Dancer, a revolutionary thorough-bred horse ‘foaled’ (word of the day?) in 1961 at businessman E.P. Taylor’s Windfields Estate fronting Bayview Avenue. I question the very liberal use of ‘near this site’ (although the farm might have extended towards Don Mills), but it’s another unexpected tidbit of North York’s rural past.

At the busy intersection of Don Mills and Sheppard, a look to the west produces the far off towers of downtown North York.

Don Mills and Sheppard Looking South 1964 — Don Mills and Sheppard Looking South, 1964. Source: City of Toronto Archives.

At the southeast corner, rainbow cones animate a nice walkup to the Emerald City condo complex. They are Douglas Coupland creations, and are the second occasion of his art showing up in Toronto suburbia – the first down the road at the Shops At Don Mills.

There’s also a Bell box covered in a jungled motif. I suppose that’s a reference to the ‘forest’ in Parkway Forest. The ‘parkway’ is naturally the Don Valley Parkway, completed here in 1966. Parkway Forest has its origins that year too, but after 40+ years was in need of revitalization and re-urbanization.

Don Valley Village is a bit of a misnomer, because I’ve been to actual Greek villages and there’s very little continuity between them and the ‘villages’ in Toronto. Emerald City – or, at least, its street layout – to me approaches that compact community feel. Coupland’s striped pencil crayons dot the streets, sprinkling new life into a space whose previous incarnation, according to the author and artist, was comparable to a World War I trench. Ouch.

There’s an interesting dynamic within this community because there are the new towers of Emerald City and then the old Parkway Forest apartments. It’s got Toronto’s two tower booms in one place – the 1960s to 1970s and 1990s to now.

Parkway Forest Ad July 21 1972 — Parkway Forest Ad, Toronto Star July 21, 1972. Source: Toronto Star Archives.

On George Henry Boulevard, there’s a pit awaiting the next phase of Emerald City.

Following Forest Manor Road down, one comes to Parkway Forest Community Centre, which looks every bit like a Diamond Schmitt creation: swanky, glassy, and energy efficient.

Leaving Parkway Forest, a venture south on Don Mills is a notable one. First, one can see the faint outlines of downtown Toronto and the CN Tower in the distance. Second, it treacherously (for me, anyways) runs over the 401, where the Peace Lady in White (I had no idea about her) has been known make her presence.

South of it, the community of Graydon Hall is named for the main landmark in the area, the Georgian-style Graydon House, which was constructed here in 1936. It was designed by Allan George and Walter Moorehouse for broker Henry Rupert Bain.

In Casa Loma-esque fashion, Graydon House is situated on a hill east of Don Mills Road, which makes for an amazing view of the gardens but also a slight feat to reach the manor.

Graydon Hall Manor Rear Henry Rupert Bain, 1950s. — Henry Rupert Bain in the gardens of Graydon Hall Manor, 1950s. Source: City of Toronto Archives.

Graydon Hall Manor gardens — The hilly Graydon Hall Manor estate, undated. Source:Graydon Historical Archive.

Its historical driveway did not lead to and from Don Mills, however, but Woodbine Avenue. Until 1964, Don Mills stopped at York Mills and was continued north when new communities – The Peanut, Parkway Forest – necessitated its existence.

Graydon Hall 1963 — Aerial of Graydon Hall and area, 1963. Source: City of Toronto Archives. Graydon House is located in the top centre. Highway 401 is north of it. Woodbine Avenue on the right. Don Mills & York Mills, bottom left.

Henry Rupert Bain died in 1952, and his manor and estate was sold to developer Normco Limited in 1964, who constructed the surrounding high-rise and residential community. Today, the house functions as a wedding and event venue.

Graydon Hall Ad July 29 1972 — Graydon Hall Ad, Toronto Star, July 29, 1972. Source: Toronto Star Archives.

Around the corner from Graydon Manor is one of the first landmarks in the new community, George S. Henry Secondary School (now Academy). Built in 1965, it celebrates its 50th year in existence in 2015. I took Saturday language classes at G.S. Henry in my teens and haven’t been back since, so it was a treat seeing the school (and actually seeing what the rest of the area looks like). Its namesake, George Stewart Henry, was a farmer of the area and a former premier of Ontario. His former residence, Oriole Lodge, is situated west of Don Mills Road near the East Don.

To end things, I make my way through the residential community and down to Duncan Mill Road. I opt for another visit to the Duncan Mills Ruins, located at the Betty Sutherland Trail.

Two years after first looking into them, the industrial relics are still a mystery to me, but it seems they might be connected to the Graydon House story. Amongst their possible uses, Jason Ramsay-Brown of Toronto’s Ravines And Urban Forests speculates that they likely were a pumping station for Henry Rupert Bain’s estate. Neat!