2012523-ossington-dundas-1920-s0372_ss0058_it0891.jpg

What Ossington Avenue used to look like in Toronto

Ossington Avenue used to have many names. Perhaps most notably (and confusingly) the stretch that now runs between Dundas and Queen West was itself known as Dundas Street until it was renamed in the early 20th century. According to the Toronto Archives, other streets eaten up by Ossington over the years include "Denison Street (By-Law No. 1115, 1881), Lancaster Road (By-Law No. 5470, 1910)... and Dundurn Avenue (Registered Plan T4395, 1924)." At one point Ossington also extended up to St. Clair, though that portion of the street was later renamed Winona Drive.

In addition to this varied nominology, the street has also enjoyed a diverse character over its history. At first a lazy road servicing John Denison's Brookfield estate, which sat at the northwest corner of Lot (now Queen) Street), there wasn't much commercial activity until the mid-19th century, around the time that the original estate was demolished. Although no photos remain from this period, even those taken in the early 20th century show the dominant presence of the Provincial Lunatic Asylum at the southern terminus of the street — which is mirrored today by redevelopment efforts at CAMH.

Ossington didn't extended north of Dundas until Garrison Creek was buried, and even today one can see traces of the former ravine throughout the area. For the most part, the character of this stretch, leading up to Bloor Street, has remained unchanged for the last 70+ years. Some photos of this area in the 1950s look eerily contemporary, though others featuring the presence of old trolley buses give their historicity away.

Although archival documentation of Ossington is decent, what we don't have much of is photos of what the street looked like between the 1960-1990s, arguably one of its most interesting iterations as a primarily industrial area. How wonderful would it be to look at images of what has now become a "trendy strip" back in the mid 1990s when auto garages and warehouses were the norm rather than the last remaining holdouts? If anyone has such photos in his or her possession, I'd love to see/share them.

This collection brings us up to the early 2000s, at which point redevelopment of the street kicks into gear. The change has been so rapid on Ossington that even Google's Streetview imagery from 2008/2009 reveals a very different place. And yet, as is so often the case, an attentive eye for the details reveals certain buildings and geographic features that have been around for 100s of years.

PHOTOS

20101116-GoadOssington.jpg

Lots of re-routing and street name changes would take place in the following years

2012523-ossington-bloor-1911-s0372_ss0058_it0049.jpg

Ossington & Bloor, 1911

2012523-ossington-harbord-1911-s0372_ss0058_it0057.jpg

Ossington & Harbord, 1911

2012523-oss-dupont-1912-f1231_it1370.jpg

Just north of Dupont, pre-rail overpass, 1912

2012523-oss-dupont-1915-f1231_it1358.jpg

Railway overpass finished, 1915

2012523-pond-btw-oss-concord-dewson-s0372_ss0100_it0171.jpg

Signs of Garrison Creek near Dewson, 1915

2012523-college-ossington-1915-s0372_ss0058_it0442.jpg

College & Ossington, 1915

2012523-oss-north-bloor-1915-s0372_ss0058_it0464.jpg

Ossington north of Bloor, 1915 (the current entrance to the TTC station would be at the bottom left of the frame)

2012523-oss-hallam-1915-s0372_ss0058_it0478.jpg

Ossington & Hallam, 1915

2012523-dundas-oss-lking-west-1917-s0372_ss0058_it0678.jpg

Dundas & Ossington looking west, 1917

2012523-oss-north-of-queen-1920-f1231_it0499.jpg

Ossington north of Queen, 1920

2012523-oss-south-dundas-lking-north-1920-f1231_it0501.jpg

Ossington near Rolyat, 1920

2012523-ossington-looking-to-queen-1920-s0372_ss0058_it0877.jpg

Looking towards Queen, 1920

2012523-ossington-foxley-1920-s0372_ss0058_it0878.jpg

Ossington & Foxley, 1920

2012523-oss-harrison-1920-s0372_ss0058_it0881.jpg

Ossington & Harrison, 1920

2012523-oss-shannon-1920-s0372_ss0058_it0882.jpg

Ossington & Snannon, 1920

2012523-oss-queen-1920-s0372_ss0058_it0888.jpg

Ossington near Queen, 1920

2012523-oss-north-to-college-1920-s0372_ss0058_it0892.jpg

Looking north toward College, 1920

2012523-st-clair-oss-1922-s0372_ss0058_it1206.jpg

Ossington & St. Clair (now Winona & St. Clair), 1922

2012523-594-ossington-ave-s0372_ss0058_it1298.jpg

594 Ossington, 1932

2012523-oss-geary-1939-s0372_ss0058_it1522.jpg

Ossington & Geary, 1939

2012523-128-ossington-1940-s0372_ss0033_it0745.jpg

128 Ossington, 1940

2012523-131-ossington-1943-s0372_ss0033_it0857.jpg

131 Ossington, 1943

2012523-67-osington-s0372_ss0033_it0949.jpg

67 Ossington, 1947

2011426-bowes-taxi-1950s-s0381_fl0319_id12641-30.jpg

Near Hepbourne, 1950s

2011513-bus-ossington-1950s.jpg

The Ossington bus in the 1950s

2012523-1054-ossington-1951-s0372_ss0033b_it0222.jpg

1054 Ossington, 1951 (this photo looks like it could have been taken yesterday)

2012523-1058-ossington-1951-s0372_ss0033b_it0224.jpg

1058 Ossington, 1951 (ditto)

2012523-ossington-queen-1958-s0372_ss0100_it0374.jpg

Ossington & Queen, 1958

2012523-oss-argyle-1958-s0372_ss0100_it0751.jpg

Ossington & Argyle, 1958

2012523-227-ossington-s1465_fl0336_it0015.jpg

227 Ossington, 1980s (this is now the Saint Tavern)

2012523-135-ossington-1991.jpg

135 Ossington, 1981 via Patrick Cummins

2012524-Toronto_Flyer_trolley_bus_1987.jpg

The 63, when it was a trolley bus, 1987 (via Wikimedia Commons)

2012523-ossington-warehouse-2001.jpg

131 Ossington, 2011 (this is now the site of O'Born Contemporary) via Kevin Steele

Photos from the Toronto Archives unless otherwise noted


Join the conversation Load comments

Latest in City

The history of Speakers Corner in Toronto

People in Toronto raise money to give man living on sailboat a place to dock for winter

This is how people in Toronto used to get their news in the 1800s and 1900s

This secluded forest in Toronto is perfect for a nature stroll

One of Toronto's most colourful bridges is being demolished

Someone just noticed an amazing hidden detail in Toronto's dog fountain

54 cannabis delivery and curbside pickup options in Toronto

The history of the Sunnylea neighbourhood in Toronto