If you see a pedestrian strolling down Liberty Street today, they could be on their way to a condo or office stacked in one of the repurposed brick warehouses still lining the road.

Just over 100 years ago they might have been taking their first steps towards freedom following a prison sentence; the narrow street that Liberty Village shares its name with was once home to a pair of correctional facilities.

Much like CityPlace, another neighbourhood that has shed its industrial roots, residential development has left its mark on Liberty Village, the west-end Toronto community bounded by King Street West to the north, Strachan Avenue to the east, the Gardiner Expressway to the south, and Dufferin Street to the west.

As part of our ongoing then-and-now-series, which also includes Mimico and Riverdale, we’ve compared present day Liberty Village shots by James Bombales with historic photos of the area.

Strachan Avenue bridge looking north, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 51, Item 15

Liberty St., looking w. from Strachan Avenue, 1926

Toronto Central Prison remains, 1953

Central Prison Land, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 58, Item 35

Liberty Street looking east from Atlantic, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 37, Item 22

Liberty Street looking east from west of Jefferson, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 37, Item 21

South-east corner of Liberty and Mowat, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 51, Item 4

Liberty Street looking east from Dufferin, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 37, Item 19

King Street looking east from Dufferin, circa 1990

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 37, Item 29

King Street West looking east across Atlantic Avenue, 1983

Historical photo: City of Toronto Archives, Fonds 1526, File 74, Item 45

Inglis lands and sign near Strachan, looking west to Liberty Village, 1980s

Historical photo: City of Toronto Archives, Fonds 200, Series 1465, File 59, Item 14

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