Kingston Road is the southernmost major road along the eastern portion of Toronto, specifically in the districts of East York and Scarborough. Until 1998, it formed a significant 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.
Native American engineer Asa Danforth Jr. was contracted to build a road as a route to connect Toronto (then called York) with the mouth of the Trent River in 1799 at a cost of $90.00 per mile. The road was completed by December 18, 1800, but was poorly maintained thereafter. In 1815 the Kingston Road was surveyed and it followed the line, in many cases, of the former road laid out by Asa Danforth. It was completed in 1817.
The Toronto section runs from Queen Street East, joining with Eastern Avenue, just west of Woodbine Avenue (route to Lake Shore Boulevard) through Scarborough to Toronto's eastern city limits with Durham Region, where it continues as Durham Regional Highway 2.
A small portion of road parallel to Kingston Road is called Old Kingston Road running near the Highland Creek, east of Morningside Avenue. The road reverts to the original route at the junction with the former Highway 2A, (as well as Military Trail). Other old, parallel sections to Highway 2, also called Old Kingston Road, exist in Courtice, Ontario and Pickering Village, Ontario. There is also an old section of the old Danforth Road in Grafton, Ontario.
The initial sections in the Beaches area take the form of a historic urban arterial road with extensive storefronts and pedestrian traffic. The TTC's 502 Downtowner and 503 Kingston Road streetcars run along Kingston Road during the daytime on weekdays (evening, weekend and holiday service is provided by buses). The speed limit in that section is 50 km/h (30 mph). Also, TTC's 12 Kingston Road, 86 Scarborough, and 102 Markham Road run along Kingston Road, east of Victoria Park Avenue.
Until Highway 401 was constructed, Kingston Road was the principal route from Toronto to points east. Accordingly, it became the site of numerous inns and motels, many of which still dot the road, particularly in Scarborough.
Now some of these inns are being demolished to make way for townhouse developments. Kingston Road is a six-lane principal arterial road through most of Scarborough and Durham, with a 60 kilometres per hour (37 mph) speed limit for the most part.
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