The following is a list of the north–south expressways and arterial thoroughfares in the city of Toronto, Ontario, Canada. The city is organized in a grid pattern dating back to the plan laid out by Augustus Jones between 1793 and 1797. Most streets are aligned in the north–south or east–west direction, based on the shoreline of Lake Ontario. In other words, major north–south roads are generally perpendicular to the Lake Ontario shoreline and major east–west roads are generally parallel to the lake's shoreline. The Toronto road system is also influenced by its topography as some roads are aligned with the old Lake Iroquois shoreline, or the deep valleys. Minor streets with documented history or etymology are listed in a separate section.
Expressways
Allen Road
William R. Allen Road, known more commonly as Allen Road, the Allen Expressway and The Allen, is a short expressway that travels from Eglinton Avenue West in the south to Kennard Avenue in the north. The portion south of Sheppard Avenue is the completed section of the proposed Spadina Expressway. Allen Road is named after Metro Toronto Chairman William R. Allen and maintained by the City of Toronto. Landmarks along the road include the Lawrence Allen Centre (formerly Lawrence Square Shopping Centre), the Yorkdale Shopping Centre and Downsview Park (formerly CFB Downsview).
Don Valley Parkway
The Don Valley Parkway (DVP) is a controlled-access six-lane expressway in Toronto connecting the Gardiner Expressway in downtown Toronto with Highway 401. North of Highway 401, the expressway continues as Highway 404 to Newmarket. The parkway runs through the parklands of the Don River valley, after which it is named. It is patrolled by the Toronto Police Service, has a maximum speed limit of and is in length.
The parkway was the second expressway to be built by Metropolitan Toronto (Metro). Planning for it began in 1954, the year of Metro's formation; the first section opened in 1961 and the entire route was completed by the end of 1966. South of Bloor Street, the expressway was constructed over existing roadways. North of Bloor Street, the expressway was built on a new alignment through the valley, requiring the removal of several hills, the rerouting of the Don River and the clearing of green space. North of Eglinton Avenue, the expressway follows the former Woodbine Avenue right-of-way north to Highway 401.
The parkway operates well beyond its intended capacity of 60,000 vehicles per day and is known for its daily traffic jams; some sections carry an average of 100,000 vehicles a day. Planned as part of a larger expressway network within Toronto, it was one of the few expressways built before the public opposition that cancelled many of the others.
Highway 404
King's Highway 404 is a provincially maintained extension to the Don Valley Parkway, north of the junction with Highway 401. Highway 404 was opened from Sheppard Avenue East to Steeles Avenue East in 1979 and extended north of the Metro Toronto limits shortly thereafter, first to Davis Drive in Newmarket and eventually to Woodbine Avenue just south of Ravenshoe Road in East Gwillimbury.
Highway 427
Most of King's Highway 427 travels within Toronto from Browns Line to Steeles Avenue, but it has been extended beyond current city limits to Major Mackenzie Drive. It was initially constructed to Highway 401 from 1953 to 1956 as the Toronto Bypass, then extended to Pearson Airport as the Airport Expressway from 1964 to 1971, and finally designated as Highway 427 in 1972. The section to Steeles Avenue West was completed in 1984.
Arterial roads
Avenue Road
There are several stories relating to the origin of Avenue Road. The most popular legend retells that of an early surveying team travelling west along what is now Bloor Street. Upon reaching the location of the intersection with Avenue Road today, the lead surveyor, a Scotsman, pointed north and proclaimed "Let's 'ave a new road here". But this is almost certainly apocryphal; the street was probably named for its tree-lined character.
Avenue Road is also a short residential street () that runs from Edgar Avenue north to Weldrick Road connecting the communities of Richvale and Yongehurst in Richmond Hill, Ontario. Although the Toronto section can align with the Richmond Hill sections if connected, the latter is a newer street not officially part of the historic Toronto roadway, unlike the disconnected York Region portions of its counterparts Kipling Avenue, Leslie Street and Woodbine Avenue. It is a part of the decommissioned Ontario Highway 11A.