Even More “Old” Streets of Toronto

This is the third article in a series explaining the origins and histories of “Old”-named streets in Toronto. Here is Part I and Part II. You will find an interactive map of the title image here.

Old Kingston Road

Year rerouted: 1922

Kingston Road once followed a “tortuous” route into the Highland Creek valley, also called the ‘West Hill Hollow’. After it passed through the village of West Hill at Morningside Avenue, it took “a sharp, twisting drop down the bank of the valley.” It then followed the floor of the valley in a straight line and crossed over the creek on “a small, concrete bridge.” Up the eastern side, the hill was straight, but with its heavy level of traffic in the summer and its steepness and low visibility, it made for a dangerous drive.

1878 Illustrated Historical Atlas of the County of York, 1878
Source: Old Toronto Maps

In early 1922, tenders called for a high-level bridge. Construction began with the expectation that the road would be ready the next year. Fortunately, the project was completed quickly and was ready in November 1922. The new route, located south of the old one, added 6,000 feet of new road.

Map of Township of Scarboro, 1933
Source: University of Toronto Map & Data Library

Today, the old route – Old Kingston Road – passes several heritage structures and offers a neat, rural drive. It is a reminder of old Scarborough.

Old Kingston Road over the Highland Creek, 2021.
Source: Google Maps

Old Forest Hill Road

Year “rerouted”: 1927

The present Forest Hill Road and Old Forest Hill Road have convoluted histories and geography, which involve the absorption, deletion, and renaming of other roads. The story of Old Forest Hill Road is unlike any of the other “Old” Streets as its changing from old to new (or new to old) did not seem to correct an inconvenience in geography.

In short, a 19th-century largely diagonal road ran through the Baldwin Estate north of St. Clair Avenue to Eglinton Avenue. In the early 20th century, a second road, which may or may not have been part of the old road, grew concurrently with it. While these were both Forest Hill Roads, in the 1920s, the ‘ancient’ road was formalized Old Forest Hill Road.

Tremaine’s Map, 1860
Source: Old Toronto Maps

The Baldwin footpath of the 1800s was originally called the “Trespass Road” (albeit likely not officially). Later, John Wickson (or someone else of the time) named this Baldwin road as ‘Forest Hill’ as it led to his 1860 summer home (or possibly one of Wickson’s pasture) of the same name.

South of Killbarry Road, this road either followed the present Dunvegan Road or a street to the east which aligns to the present Forest Hill Road — or possibly followed both at different times. Whichever is the case, another Forest Hill Road developed south and east (and later north and east) of the older Forest Hill Road beginning in the first or second decade of the 1900s. This meant that, at one time, there were two unconnected Forest Hill Roads. To ease (or complicate) matters more, the older road was sometimes referred to as Forest Hill Road North.

Map of Toronto, 1908.
Source: City of Toronto Archives Fonds 200, Series 726, Item 19r

In the 1920s, the matter was cleared as the street grid filled out, and the neighbourhood gained a formal identity. In 1923, the area was organized into the Village of Forest Hill, borrowing its name from the old Wickson home. Old Forest Hill Road began to gain more use, and by 1927, it was the official name for the old road.

Might’s clearview correct city directory map of greater Toronto, 1934
Source: City of Toronto Archives

North of Eglinton Avenue, Old Forest Hill Road later absorbed part of Whitmore Avenue east of the present Allen Road (the highway bisected the street and its eastern section joined with Old Forest Hill Road). Whitmore was previously Second Avenue. This area is known as Forest Hill North and has the oldest house in the region as a whole: the William Moore House.

Today, Old Forest Hill Road is a beautiful street with some of the most exclusive addresses in Toronto and Canada.

Old Forest Hill Road looking north Dunvegan Road, 2020. The house on the left was formerly resided by Lady Flora Eaton.
Source: Google Maps

Note: A HUGE Thank You to Kiki M and her amazing resourcefulness and knowledge of Forest Hill . Follow her Toronto History offerings on Instagram and TikTok.

Old Gerrard Street

Year rerouted: 1930

Gerrard Street once ran an awkward course where it crossed Carlaw Avenue. The Canadian National Railway curled northeast through the intersection and made for an indirect east-west path. An eastbound traveler needed to jog southeast onto Carlaw under a 19th century rail subway and then northeast again on Gerrard before continuing straight east towards Pape Avenue.

Gerrard and Carlaw, 1915. View is looking west from Old Gerrard, showing the curved jog.
Source: City of Toronto Archive
Goad’s Fire Insurance Map, 1924
Source: Goad’s Toronto

In 1929, the plan was to straighten Gerrard under the CNR bridge. It would cost $312,000. The idea was as old as the beginning of the decade. In 1930, a second subway was built on Gerrard Street, which finally eliminated the need to jog through the intersection. In 1931, the original subway was also reconstructed to match the new one, giving us the imposing infrastructure we see today.

Old and New Gerrard Street, 1930. View is looking west. The new straightened Gerrard is straight ahead with the old course with the old subway on the left.
Source: City of Toronto Archives

When the intersection was reconfigured, the old diagonal stretch of Gerrard remained. On old maps, the old jog largely went unlabelled, and in city directories, there was no distinction between the two Gerrards as the street numbering did not have to change when the subway was built. Although it never formally became “Old Gerrard Street,” there were some references to it in name.

Might’s clearview correct city directory map of greater Toronto, 1934
Source: City of Toronto Archives
The Globe Dec 24, 1941
Source: Globe and Mail Archives

In 2002, its northern opening where the two Gerrards crossed was closed to through traffic. Today, the former jog creates navigational issues for motorists who turn too early onto Gerrard and end up in a residential neighbourhood instead of the “main” Gerrard Street.

Looking northeast on Old Gerrard Street, 2020.
Source: Google Maps

Old Burnhamthorpe Road

Year rerouted: 1970

The old Concession II was the root of the present Burhamthorpe Road. According to the Etobicoke Historical Society:

“In 1846, it [Concession II] became the Etobicoke and Mono Sixth Line Plank Road, a toll road that began at Dundas Street where Burnhamthorpe Crescent is today, and ran west on Burnhamthorpe Road, then north on Mercer Road (now Elmcrest Road) and west on Base Line East (now Eglinton Avenue West.)”

Etobicoke Historical Society

Tremaine’s Map, 1860.
Source: Old Toronto Maps

Burhamthorpe ran northeast from the Etobicoke-Mississauga townline and then dropped southeast before continuing straight east to the Village of Islington at Dundas Street. The route possibly followed old property lines and roads.

By 1970, Burhamthorpe Road was realigned via a new road which offered more direct route between Etobicoke Creek and Renforth Road. The older section was renamed Old Burnhamthorpe Road.

Old and New Burnhamthorpe Roads, 1970.
Source: City of Toronto Archives

Today, Old Burhamthorpe Road blends into the surrounding post-war neighborhood. The 1820 Mercer House stands at 72 Old Burhamthorpe as a reminder of the route’s former history.

Old Burhamthorpe Road, looking northeast. The Mercer House is on the left.
Source: Google Maps.

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.

Looking southeast from University Avenue, 1920. Source: City of Toronto Archives. Annotations by Bob Georgiou.

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.

Looking southeast from University Avenue, c 1920. Source: City of Toronto Archives.

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.

Alexandra Palace Apartments, No. 184-188 University Avenue (erected 1909), 1919. Source: City of Toronto Archives.

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.
Alexandra Apartments, University Avenue, west side, between Elm & Orde Streets, 1954. Source: Toronto Public Library.

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).

Looking north from top of Eaton’s factory, c 1910. Source: City of Toronto Archives. Annotations by Bob Georgiou.

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).

T. Eaton Company factory from Louisa Street, 1910. Source: City of Toronto Archives.
The Eaton’s store, the Eaton’s Annex, mail order facilities and factories in Toronto, at Yonge and Queen Streets, in 1920. Source: Wikimedia Commons.

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.

T. Eaton factory from Louisa Street, c 1920. Note the addition of the north tower (1920). Source: City of Toronto Archives.

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.

A modern view of the area formerly known as The Ward, 2021. The sites of The Alexandra Apartments and Eaton’s factory are circled. Source: Google Maps.