Ossington Avenue may now be known for its restaurants and bars today but a decades ago, the west end street was considerably more down on its luck.

We took historic photos of the avenue and its neighbours and matched them with modern-day snapshots. Take a look at the interactive sliders below to see just how much the neighbourhood has changed. All modern day photos are by James Bombales. All historic pictures are from the Toronto’s Public Library’s Digital Archive unless otherwise specified.

129 to 133 Ossington Avenue, 1943

Image: City of Toronto Archives, Series 372, Item 857

Ossington and Queen, Columbia Hotel, 1955

Gates of Trinity College, 1916

Image: City of Toronto Archives, Fonds 1244, Item 1516

128 Ossington Avenue, 1940

Image: City of Toronto Archives, Series 372, Item 745

Ideal Bread Company, 183-193 Dovercourt Road, at Argyle Street, 1923

Image: City of Toronto Archives, Fonds 1034, Item 839

Ossington Avenue and Argyle, looking west, 1958

Image: City of Toronto Archives, Series 372, Item 750

Ossington Avenue at Foxley Street, 1920

Image: City of Toronto Archives, Series 372, Item 878

Ossington at Bloor Street, looking east, 1931


Image: City of Toronto Archives, Series 71, Item 8413

Ossington and Bloor, looking north, 1931

Image: City of Toronto Archives, Series 71, Item 8414

Want to see more? Check our history sliders of Dufferin Street, Midtown Toronto, Roncesvalles, Yorkville and Spadina.

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