List of diagonal roads in Toronto

Albion Road

Albion Road was created as a private road for French teacher Jean du Petit Pont de la Haye to his estate in the area. Originally called Clairville, it was renamed for the Albion Township just north of the area in what is now Brampton, Ontario. The road is located within Toronto, starting at the intersection of Weston Road and Walsh Avenue (continues eastward as Wilson Avenue) and heads northwest to Albion and Steeles (becoming County Road 50).

The beginning of the road is Walsh Avenue a short connector between Albion Road and Wilson Avenue, The intersection at Weston Road and Walsh Avenue is a ramp with two traffic lights for Albion Road/Walsh Avenue and none for Weston Road.

Albion Road northwest of Highway 27 was formerly Highway 50, but now is Regional Municipality of Peel Road 50, and then Simcoe County Road 50. The end of highway 50 is Ontario Highway 89 by the town of New Tecumseth.

Albion Road is weaved by TTC routes 73C and the southern section is served by route 118.^[1]

Black Creek Drive

Black Creek Drive was originally constructed as a southward extension of Highway 400. However, it was built as an arterial road instead, due to the opposition of extending the Spadina Expressway south of Eglinton Avenue, which in turn led to the cancellation of other expressway extensions in Toronto. The street has few intersection at Lawrence Avenue, Trethewey Drive, Todd Baylis Blvd, Eglinton Avenue and it ends at Weston Road. The street is not served by any TTC routes.^[1]

Danforth Road

Danforth Road is a historically-related arterial street in Toronto, Ontario, Canada. Danforth Road splits off Danforth Avenue west of Warden Avenue, and runs diagonally northeast until south of Lawrence Avenue, where it continues as McCowan Road. McCowan road ends at Baseline Road located in York Region.

Line 2 Bloor–Danforth of the Toronto subway runs just north of Danforth Avenue from the Don River as far as Main Street station, before gradually veering north as it heads east. The route is also served by TTC route 16.^[1]

Kingston Road

Kingston Road is the southernmost major road along the eastern portion of Toronto, specifically in the district of Scarborough. Until 1998, it formed a portion of Highway 2. The name of the street is derived from Kingston, Ontario as the road was the primary route used to travel from Toronto to the settlements east of it situated along the shores of Lake Ontario; in the west end of Kingston, this highway was referred to as the York Road (referring to Toronto) until at least 1908. Due to its diagonal course near the shore of Lake Ontario, the street is the terminus of many arterial roads in eastern Toronto, both east-west and north-south, with a few continuing for a short distance after as minor residential streets. However, Lawrence Avenue continues as a major arterial for a considerable distance beyond it.

Kingston Road is served by Toronto Transportation Commission routes 502/503/22A, 12, 102 and 86/86E/198.^[1]

Rexdale Boulevard

Rexdale Boulevard
Location	Islington Avenue - Highway 427

Rexdale Boulevard is a short, but major east-west but mostly diagonal roadway in Rexdale, a neighbourhood in Toronto, and begins as a spur road off Islington Avenue just north of the 401. This spur originally began in the former village of Weston as a road northwest to what would later become Brampton, Ontario. The current road passes through a mostly light industrial stretch of north Etobicoke. West of Highway 427, Rexdale becomes Derry Road and enters the city of Mississauga, Ontario. Derry is also signed as Peel Regional Road 5, an east–west route that travels the entire length of the city of Mississauga and Peel Region. Derry Road is the northern boundary of Toronto Pearson International Airport. The intersection of Derry and Airport Road was once the site of Malton, itself a part of Mississauga. At the intersection with Mavis Road, the road makes a large jog around the former village of Meadowvale. This jog created a stretch of road called Old Derry Road and can also be seen in a small stretch of Syntex Crescent. Derry Road is named for the "lost village" of Derry West, which was located around the Hurontario and Derry intersection.^[2] Derry West was named after Derry (officially Londonderry) in Northern Ireland and home of many settlers in the area.

West of Highway 407, Derry Road enters Halton Region as Halton Regional Road 7. This stretch of road is mainly rural except for the section between James Snow Parkway and Tremaine Road in Milton. After passing through another rural stretch, the road ends at Milburough Line in the town of Carlisle in Hamilton (formerly in Flamborough before amalgamating with Hamilton in January 2001).

The street is served by TTC route 37A .^[1]

Chaplin Crescent

Chaplin Crescent is served by TTC route 14 Glencairn.^[1]

Chaplin Crescent is a diagonal street located in Toronto, Ontario. The street runs almost entirely just north of the Kay Gardner Beltline Park, a former railway meant to serve the community of Forest Hill. The street has several parks on it: Forest Hill Memorial Park, Larratt Parkette, Robert Batman Parkette, and Oriole Park.^[3] At the southeast end of the street where it crosses Yonge Street, it become Davisville Avenue.^[4]

Dawes Road

Dawes road is a spur of Victoria Park Avenue. The street has a bridge over the Massey Creek. The street between Victoria Park and Pharmacy Avenue is a east–west road running just south of St. Clair Avenue. There is a 50-metre gap between the east-west Dawes Road and the diagonal Dawes Road. Dawes Road is served by TTC route 23.^[1]

Trethewey Drive

Trethewey Drive, formerly named Holmstead Drive, was a private rural road on mine owner W.G. Trethewey's farm. In 1910, the property became the site of Toronto’s first airplane flight, with French ace Count Jacques de Lesseps circling the city. Trethewey Airfield, later renamed De Lesseps Field, hosted de Havilland Canada and the Royal Canadian Air Force before the land was sold for development in 1941.^[5][6] The boroughs of North York and York later assumed control of the road.

The street is served by TTC route 32C (may change when Line 5 Eglinton opens.)^[1]

Vaughan Road

Vaughan Road is aligned northwest-southeast between Bathurst and St. Clair. Note the single streetcar track in the Old Toronto segment.

Vaughan Road is named after the Township (later City) of Vaughan, which in turn was named after Benjamin Vaughan, a British commissioner whose role was to smooth negotiations between Britain and the United States during the drafting of the Treaty of Paris in 1783. The neighbourhood of Oakwood–Vaughan, as well as former high school Vaughan Road Academy, are named after this street. Vaughan Road's contour is the result of it being parallel to the partially buried Castle Frank Brook to the northeast.

Vaughan Road is served by TTC bus route 90,^[1] there are streetcar tracks on the road south of St. Clair to allow 512 St. Clair streetcars to go to the depots located closer to the lakeshore, by the rest of the TTC streetcar system.