Well before Bayview Avenue became one of Toronto's most prominent north-south corridors, the road was surrounded by acres of farmland, grand estates belonging to wealthy businessmen and financiers, and large stretches of undeveloped land.
Originally laid out as the first concession road east of Yonge Street, the route was surveyed in the late 18th century, and later became known as East York Avenue, as a reference to the boundary it formed between Toronto and the township of East York.
By the early 20th century, the landscape around Bayview was shifting rapidly, as residential neighbourhoods were taking shape and massive estates occupied large swaths of land, many of which overlooked the Don Valley.
One notable property in this area was "Bay View," a 55-acre estate on the east side of Bayview Avenue belonging to meat packer James Stanley McLean (you can probably guess now where the street got its name). Today, the home is known as McLean House, and is situated on the Sunnybrook Hospital campus.
In 1929, the opening of the original high-level Bayview Bridge over the West Don River helped to improve connections across the Don Valley, and three decades later, the Bayview Extension carried the road south from Moore Avenue toward Front Street as part of the major post-WWII road-building projects that reshaped Toronto.
Bayview Avenue has changed drastically over the years, and these photos offer a glimpse at just how different it once looked.

Nearby: Queen Street Viaduct, Queen Street at Don River in 1911. Bayview Avenue runs beneath the viaduct today.
Nearby: Prince Edward Viaduct under construction in 1917. Bayview Avenue passes underneath the bridge today.
Nearby: Prince Edward Viaduct pictured in 1922. Bayview Avenue now runs beneath the historic bridge.
558-564 Bayview Avenue in 1932.
Bayview Avenue and Lawrence Avenue East.
Construction of bridges on Lawrence Avenue East and Bayview Avenue.
Bayview Manor Apartments at 1220 Bayview Ave. in the 1950s.
View of the construction of the new section of the Bayview Bridge, looking north in 1960.
View of the construction of the new section of the Bayview Bridge, looking north in 1960.
The unfinished Hampton Park apartments (known as the Bayview Ghost) pictured in the 1960s. Construction ceased in 1959 and the shell of a building sat abandoned for decades.
View of the east side of the Bayview Bridge, looking south in 1960.
Steeles Avenue East and Bayview Avenue in 1965.
Don Valley Parkway and Bayview Avenue, looking southwest, sometime between 1964 and 1972.
Bayview Avenue looking north from Manor Road in 1980.
Bayview Avenue looking south from Belsize Drive in 1980.
Bayview Avenue looking north from Millwood Road in 1980.
Bayview Avenue looking north from Belsize Drive in 1980.
Bayview Avenue looking north from Soudan in 1980.
Bayview Extension south of Dundas Street, looking north, sometime between 1983 and 1992.
Looking south on Bayview Avenue to the Gardiner Expressway in 1989 or 1990.
Bayview Avenue, looking north to Queen Street in 1991.
City of Toronto Archives