The following is a list of the east–west expressways and arterial thoroughfares in 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. Roads are listed south to north.

Expressways

Gardiner Expressway

The Frederick G. Gardiner Expressway, known locally as "the Gardiner", is an expressway connecting downtown with the western suburbs. Running close to the shore of Lake Ontario, it now extends from the junction of Highway 427 and the Queen Elizabeth Way (QEW) in the west to the foot of the Don Valley Parkway in the east, just past the mouth of the Don River. East of Dufferin Street, the roadway is elevated, running above Lake Shore Boulevard east of Bathurst Street, making this stretch of Gardiner Expressway unofficially the longest bridge in Ontario. Elevated sections east of the Don River were demolished and integrated into Lake Shore Boulevard.

The highway is named for the first chair of the Metropolitan Toronto Council, Frederick G. Gardiner; the council was dissolved in 1998. The six-lane section east of the Humber River was built in segments from 1955 until 1964 by the Metropolitan Toronto government with provincial highway funds. The ten-lane section west of the Humber River was formerly part of the QEW and is now wholly owned and operated by the municipal government of Toronto.

When the Gardiner was built, it passed through industrial lands, now mostly converted to residential lands. Extensive repairs became necessary in the early 1990s, and since then, the Gardiner has been the subject of several proposals to demolish it or move it underground as part of downtown waterfront revitalization efforts. One elevated section east of the Don River was demolished in 2001, and a study is underway to demolish that part of the elevated section east of Jarvis Street to the Don River.

Highway 401

King's Highway 401, colloquially referred to as the four-oh-one, opened between December 1947 and August 1956, and was known as the Toronto Bypass at that time. Although it has since been enveloped by suburban development, it still serves as the primary east–west through route in Toronto and the surrounding region. East of the Don Valley Parkway, it is also known as the Highway of Heroes, in reference to the funeral processions travelling between CFB Trenton and the Ontario Coroners Office in Downtown Toronto, the latter of which was moved to Hennick Humber Hospital grounds on Wilson Avenue west of Keele Street in 2013. Highway 401 crosses the entirety of Toronto and physically divides the city into a northern third and a southern two-thirds. It is also known as the Macdonald–Cartier Freeway.

Highway 401 is the busiest freeway in North America and among the widest on the continent.

Highway 409

Ontario Highway 409 or Belfield Expressway opened in 1978 to provide access to Toronto Pearson International Airport from westbound Highway 401 at Islington Avenue. The section east of Highway 427 is within Toronto, while the remaining sections west are within the City of Mississauga. The expressway is maintained by the Ministry of Transportation of Ontario and the Greater Toronto Airports Authority. The alternate name is taken from nearby Belfield Road, which begins from the westbound off-ramps for Kipling Avenue.

Arterial roads

Queens Quay

Queens Quay begins west of Bathurst Street at Stadium Road and ends at Lake Shore Boulevard East, where it continues north as Parliament Street. The roadbed is built entirely on infill and is the closest road to Lake Ontario throughout the downtown core. Though once abutted by industrial and transportation uses from end to end, much of its length is now lined with recreational and residential uses. The 509 Harbourfront streetcar line now travels in a dedicated streetcar right-of-way in the median from Bay Street to Bathurst Street. The length east of Yonge Street retains some industrial uses, although this is changing with the development of residential and commercial uses.

In 2015, Waterfront Toronto announced its plans to turn Queens Quay into a grand lakefront boulevard by placing streetcar lanes in the centre, traffic only on the north side and a bicycle and pedestrian focused space on the south side. The plan reduces the number of traffic lanes on Queens Quay to two, to the north side of the streetcar tracks. Additionally, the plan calls for the beautification and extension of the Harbourfront streetcar line along Queens Quay East between Yonge and Cherry streets. The newly modified Queens Quay was completed in 2015 from Bathurst Street to Bay Street.

Lake Shore Boulevard

Lake Shore Boulevard, often incorrectly compounded to Lakeshore Boulevard, is so named because of its course along the Lake Ontario shoreline. Although the road west of Roncesvalles Avenue (which was the eastern terminus of the original Lake Shore Road, which continued as Queen Street) has existed since the 19th century, much of the remainder of the route was created between the 1920s and 1950s. Lake Shore Boulevard east of the Humber River was doubled in width by widening into the right of way of Lake Shore Road, replacing it, which resulted in the demolition of the rail overpass leading to the Queen/Roncesvalles intersection by 1960. Incorporating various streets (that mostly formed the original route of former Highway 2) such as Laburnam Avenue, Starr Avenue and Dominion Street, the route was pushed east to Bathurst Street on January 28, 1924.City of Toronto Bylaw 9884 (1924) From there, it continued as Fleet Street to Cherry Street, incorporating a segment of the latter. Keating Street continued east from a point just south of that intersection to Leslie Street, and a new extension was built to turn north to tie into a short southerly extension of Woodbine Avenue. These three streets were reconstructed to form a continuous roadway, and renamed as part of Lake Shore Boulevard on August 25, 1959.City of Toronto Bylaw ?.

West of downtown, Lake Shore Boulevard is served by TTC streetcar routes 501 Queen and 508 Lake Shore.

Mill Street

Mill Street runs from Parliament Street to Bayview Avenue. Now associated with the heritage Distillery District, Corktown, Toronto and Mill Street Brewery, the road was named in reference to the Toronto Rolling Mills, a rail-making plant founded by Sir Casimir Gzowski in 1857 that was once located at Rolling Mills Road (once called East Street and later Water Street) until 1874 and torn down for use as Grand Trunk Railway railyard (now used by GO Transit). Mill Street Brewery, owned by InBev, is named after this street and continues to maintain a brewery and restaurant on that street in the Distillery District.

Front Street

Front Street is so named because it fronted the Lake Ontario shoreline at the time of the original layout of York. The early street was called Palace Street. In the early years of the 20th century, the Toronto Harbour Commission revitalized the stagnant industrial waterfront. Largely as a result of this process, the shoreline was filled several hundred metres south to Queens Quay.

Front Street begins at Bathurst Street and crosses through downtown Toronto north of the rail viaduct. The road passes the Metro Toronto Convention Centre, the CN Tower and Union Station before eventually merging with Eastern Avenue. A short side street section branches off at the diversion and continues east to Bayview Avenue.

Wellington Street

Wellington Street is a one-way westbound street north of Front Street. Wellington Street begins at Church Street and cuts through downtown Toronto, passing through the Financial District and ends at Strachan Avenue, then continues as Douro Street (once the name for the section from Bathurst Street to Strachan Avenue) until King Street West. Wellington Street is cut off at Clarence Square and vehicles cannot connect with east or west of Spadina Avenue. Wellington Street is likely named after Arthur Wellesley, 1st Duke of Wellington. In maps in the early years of York, the street was called Market Street in reference to the street to the south of Market Square.

The street passes by a number of small urban parkettes:

Berczy Park (named after William Berczy) Pecaut Square – formerly Metro Square and named after David Pecaut Clarence Square Victoria Memorial Square

The 503 Kingston Rd streetcar route runs on a single track between Church Street and York Street.

Eastern Avenue

Eastern Avenue, formerly South Park Street, was named on November 27, 1876.City of Toronto Bylaw 764 (1876) It was connected with Kingston Road in 1998 following the removal of the old Woodbine Racetrack.City of Toronto Bylaw 813-1998 Eastern Avenue begins at a curve along Front Street east of Parliament Street; eastbound traffic on Front is defaulted onto Eastern Avenue, vice versa for westbound traffic on Eastern. The road crosses the Don River, merging with Richmond Street and Adelaide Street and providing access to the Don Valley Parkway. East of Broadview Avenue, it travels parallel to and three blocks south of Queen Street East along the King Street alignment to east of Coxwell Avenue, where it curves northward and meets Queen Street. North of Queen Street, the road becomes Kingston Road.

King Street

King Street was named in honour of King George III by John Graves Simcoe when it was laid out in the original plan of York in 1793. It has had various names over the years. The street travels east from the Queensway, splitting off to the southeast at Queen Street West and Roncesvalles Avenue, to the Don River where it ends at Queen Street East. The central section of King Street has a transit mall named King Street Transit Priority Corridor to accommodate streetcar routes along King Street.

Adelaide Street

Adelaide Street was named after Princess Adelaide of Saxe-Meiningen (wife of King William IV) by Peter Russell, second Lieutenant Governor of Upper Canada, in his 1797 plan of Toronto. The original section of Adelaide Street was only a portion of the present street. In 1844, Little Adelaide Street, Adelaide Street and Newgate Street were amalgamated to form Adelaide Street from Jarvis to Bathurst Street.City of Toronto Bylaw 84 (1844) The street was split into east and west sections in 1884.City of Toronto Bylaw 1526 (1884) In 1926, at the request of property owners, Adelaide Street West was extended from Bathurst Street to Shaw Street, incorporating the entirety of Defoe Street and McDonnell Square.City of Toronto Bylaw 10675 (1926)

The most recent extension came in 1965, when Adelaide Street East was routed eastward onto Duke Street, which crossed between Jarvis Street and Parliament Street.Municipality of Metropolitan Toronto Bylaw 2430 (1965) This was done in advance of the opening of the lower section of the Don Valley Parkway and the eastern section of the Gardiner Expressway. Newgate and Duke Streets were amalgamated into Adelaide Street East and a connecting road was built from Parliament to the Parkway at Eastern Avenue where an on-ramp connects to the northbound Parkway. At the same time, the newly-extended Adelaide was converted to a one-way street in the easterly direction. Between the Eastern Avenue ramp and Bathurst, Adelaide serves as the eastbound member of a one-way pair, together with Richmond Street as the westbound member.

Richmond Street