Ossington Avenue is a main or arterial street in Toronto, Ontario, Canada, west of downtown.

[3]) The origin of Ossington Avenue[4] lies in John Graves Simcoe's 1793 plan for a western military road from York, the new capital of Upper Canada.

A more northerly route was substituted, and cut by the Queen's Rangers under the direction of Captain George Taylor Denison, completed by 1817.

Its first segment continued west along Queen Street West, crossing Garrison Creek, and running to the eastern edge of Park Lot 25 (purchased not long before by Denison himself); a short 560-metre (1,840 ft) segment then turned north, running between Denison's Park Lot 25 and the neighbouring Park Lot 24 of James Givins; upon meeting an ancient First Nations "desire path" trail following the high ground beneath the western fork of Garrison Creek, the route turned again west along this natural contour, forming the final segment of Dundas Street (and by far the longest, running approximately 70 kilometres (43 mi) west to the town of Dundas, Ontario, along the route of contemporary Dundas Street West).

By 1884, a street named "Ossington Avenue" had been constructed, running north from Dundas to Bloor Street,[8] and by 1890, as far as St. Clair[9] (though the section north of Davenport was eventually renamed to Winona Drive, and contemporary Ossington Avenue ends at Davenport).

[11] In 1968, after assassinating Martin Luther King Jr., James Earl Ray fled to Toronto and lived in a rooming house on Ossington Avenue.

A double murder in a karaoke bar that year sparked neighbourhood action in concert with the police to cut down on crime.

By 2009, the number of bars and restaurants created tension with residents of the surrounding neighbourhood, and licensing controls were imposed to stop the opening of more businesses of the same kind.

From this intersection north to Dundas, Ossington is largely lined with low-rise retail storefronts, typically with apartments on upper floors; other buildings house light industrial uses.