What Queens Quay used to look like in Toronto

It goes without saying that Toronto's waterfront has transformed dramatically over the past century, and what was once a gritty industrial corridor filled with active piers, docks, and factories is now lined with green spaces, condo towers, and plenty of restaurants.

Before the 1920s, the Esplanade was the city's southernmost street, but as Toronto rapidly expanded, a massive infill project pushed the waterfront further down south, allowing Queens Quay to be built as an access road for the inner harbour's ports and slips.

Before we delve into its history, we can't proceed without acknowledging that Queens Quay (not Queen's Quay) is arguably one of the city's most commonly mispronounced streets. Despite its spelling, "quay" is pronounced "key," which is a reference to the street's origins as a waterfront wharf. 

For most of the 20th century, the waterfront area remained focused on trade and industry. Between Yonge Street and Parliament Street, Queens Quay was home to numerous buildings connected to shipping, including the Redpath Sugar Refinery.

It wasn't until the 1970s that the street began its transformation into the neighbourhood we recognize today, with developments like the Toronto Star building, which officially opened in 1971, and the Westin Harbour Castle in 1975.

A lot has changed since the 1920s, so let's take a step back in time to see what Queens Quay used to look like in Toronto.

Photos 

Queens Quay west from Bay Street in 1927. 

Queens Quay looking east from York Street in 1927, showing construction of TTC and CPR tracks. 

Looking north from Queens Quay, showing new alignment of south Bay Street on landfill over former harbour area in 1927.

Redpath Sugar on Queens Quay East looking west in 1970.

Waterfront looking east from Bay Street from above, between 1970 and 1987.

Queens Quay West just west of Spadina Avenue, looking east in 1976.

Maple Leaf Mills on Queens Quay West, looking east from between Rees Street and Spadina Avenue in 1976. 

Queens Quay East looking east to Cherry Street in 1976. 

Queens Quay West at Spadina Avenue, looking west in 1976. 

Queens Quay East at Redpath Sugar, looking east from west of Cooper Street in 1976. 

Queens Quay East, looking east from just west of Freeland Street in 1976. 

West end of Queens Quay West, looking north to Tip Top Tailors in 1978.

Queens Quay, looking west to Bathurst Street, sometime between 1980 and 1998.

Queens Quay, looking east from west of Spadina Avenue, sometime between 1980 and 1998.

Parking lot on Queens Quay east of Yonge Street, looking south, sometime between 1980 and 1998. 

Looking south to waterfront at the foot of Yonge Street, sometime between 1981 and 1984. 

Queens Quay, looking east to Spadina Avenue, sometime between 1984 and 1990. 

Queens Quay, looking west from Jarvis Street, sometime between 1984 and 1990.

Queens Quay looking east from Cooper, sometime between 1984 and 1990.

Foot of Yonge Street at Queens Quay, looking east, showing Captain John's restaurant sometime between 1985 and 1998.

Streetcar on Queens Quay, looking east to Rees Street in 1990. 

A streetcar emerging from the tunnel to Queens Quay, looking east to Bay Street in 1990. 

Building on Queens Quay looking northeast to Spadina Avenue in 1991.