Dufferin Street starts at Lake Ontario in Toronto, cutting through the city all the way up to York Region towards farm fields and concession roads.

Between Bloor and the waterfront, Dufferin passes through residential neighbourhoods and parts of the city once known as hubs of industry. As part of our series comparing Toronto the Old to Toronto the New, we decided to take a closer look at Dufferin Street, and some of its neighbouring streets, to see just how much this major thoroughfare has changed over the years. All modern photos are by James Bombales.

Queen Street, looking south down Dufferin, 1897

Image: City of Toronto Archives/Fonds 200, Series 376, File 2, Item 10

Gladstone Hotel, Northeast corner Gladstone Avenue and Queen St, 1952

Image: Toronto Public Library Digital Archives

Bombs stored on Liberty Street, looking east from Dufferin Street, 1915

Image: City of Toronto Archives/Fonds 1244, Item 848

Bloor Street West, northeast corner of Bartlett Avenue, 1944

Image: Toronto Public Library Digital Archives

Toronto Public Library Bloor and Gladstone Branch, southwest corner Gladstone Avenue and Bloor, 1913

Image: Toronto Public Library Digital Archives

Dufferin Street, looking north from College Street, before the widening of Dufferin, 1948

Image: City of Toronto Archives/Fonds 200, Series 372, Subseries 58, Item 1813

Lindsey Avenue, looking west from Dufferin Street, showing Mrs. Nottingham buying bananas, 1910

Image: Toronto Public Library Digital Archives

Pete’s Meat Market, Bloor Street West, north side, between Concord and Delaware Ave, 1953

Image: Toronto Public Library Digital Archives

Dundas and Dufferin, looking east, 1951

Image: City of Toronto Archives/Fonds 1231, Item 115

Dufferin Street, before widening, just south of Bloor, looking north, 1948

Image: City of Toronto Archives/Fonds 200, Series 372, Subseries 58, Item 1817

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