At the outset of the 20th century, St. Clair Avenue was a narrow stretch of road, bordered by stretches of farmland and broken by a series of ravines to the east of Yonge Street.

Thanks to various annexation efforts, the majority of the street fell within the city of the Toronto by 1911, at which point the construction of streetcar track ushered in a development boom that would rapidly change the character of the street. 

Archival photos show just how closely linked St. Clair's history is linked the streetcars. From the old car barns at Wychwood to the passenger safety zones of the the 1920s, to the still-remaining loop at St. Clair Station, the streetcar has been a ubiquitous presence on the west side of the street for just over a century.

Here is what St. Clair Avenue used to look like.

Hunting group on Bathurst north of St. Clair, 1900s

Southwest corner of Yonge and St. Clair, 1911

Northwest corner of St. Clair and Dufferin, 1911

Southwest corner St. Clair and Dufferin, 1911

Northeast corner of Spadina and St. Clair.

St. Clair and Caledonia, 1911

Looking west on St. Clair toward Bathurst, 1911

Looking east along St. Clair at Vaughan, 1912

TTC Car Barns (now Wychwood Barns), 1915

Mt. Pleasant and St. Clair, 1922

Southwest corner of Yonge and St. Clair, 1923

Looking east on St. Clair at Mulock, 1923

St. Clair Bridge under construction, 1924

Oops at St. Clair and Rushton, 1926

Looking east on St. Clair at Oakwood, 1927

Looking east on St. Clair at Rushton, 1928

Looking east on St. Clair at Christie, 1928

Looking east on St. Clair at Wychwood, 1928

Avenue Rd. & St. Clair, 1928

Looking east on St. Clair at Vaughan, 1928

Looking west to Bathurst on St. Clair, 1928

Abattoirs in the distance near Weston Road, 1930

Private property on St. Clair west of Keele, 1933

St. Clair Reservoir, 1934

Canada Packers stockyards, 1940

Granite Club, west of Yonge on St. Clair 1947

Brand new St. Clair Station, 1954

St. Clair Station streetcar entrance, late 1950s

990 St. Clair West, 1957

Spadina and St. Clair, 1958

Stockyards near Keele, 1959

Loblaws property on St. Clair east of Bathurst, 1974

Alternate angle of the Loblaws. 

Yonge and St. Clair, 1980s