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.

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.

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 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.

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.

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.

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.

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.

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.

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.

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.

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

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.

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.