Old Photographs of Bicycles in Toronto (1907-1960)

Embark on a nostalgic two-wheeled journey through the historic streets of Toronto with our curated collection of vintage photographs, showcasing the rich bicycling heritage that has peddled its way through the city’s heart. From the early 20th century charm of cyclists gliding across Centre Island in 1908 to the thrilling races at Scarborough Beach Park’s Velodrome circa 1926, these images, sourced from the Toronto archives, breathe life into the evolving culture of cycling captured between 1907 and the 1960s. I wanted to share with our readers some of my favourite images of locations of yesteryear’s bicycling events, the evolution of bicycle designs, and the admirable bicycle corps in their prime, this blog post promises a ride through Toronto’s picturesque past, filled with nostalgia and the timeless spirit of bicycling. Enjoy!

Old Photographs of Bicycles in Toronto (1907-1960)
Boys cycling across Lakeshore Road bridge at Mimico. – [1907?]
Old Photographs of Bicycles in Toronto (1907-1960)Photographs
Female cyclist wheeling bicycle up muddy hill on St. Clair Avenue West. – 1907
Cycling in Rosedale Valley - Vintage Bicycle Photographs
Cycling in Rosedale Valley – between 1900 and 1920
Bill James Jr. and his first Canadian bicycle. - 1907 - Vintage Bicycle Photographs
Bill James Jr. and his first Canadian bicycle. – 1907
Some of the James family. - 1907. A note says this may be 39 Huron Street, but the house isn't the same as in 3522. - Vintage Bicycle Photographs
Some of the James family. – 1907. A note says this may be 39 Huron Street, but the house isn’t the same as in 3522.
Sis, Aunt Alice, Dora, and Frank (on bicycle) James. - 1907 - Vintage Bicycle Photographs
Sis, Aunt Alice, Dora, and Frank (on bicycle) James. – 1907

Old Photographs of Bicycles in Toronto (1907-1960)Cyclists, Centre Island. – 1908

Bill and Joe James in a motorcyle with side car. - [1910?] - Vintage Bicycle Photographs
Bill and Joe James in a motorcyle with side car. – [1910?]
Cycling beside Don River, between Don Mills Road and Leaside . - [ca. 1912] - Vintage Bicycle Photographs
Cycling beside Don River, between Don Mills Road and Leaside . – [ca. 1912]

Bicycle corps, University Avenue. - 1913 - Vintage Bicycle Photographs
Bicycle corps, University Avenue. – 1913

Soldier with family. - [1914?]. A note says that the location is the city limits of Hamilton, where soldiers on a trek were met by their families. (However, the soldier shown has a bicycle.) - Vintage Bicycle Photographs
Soldier with family. – [1914?]. A note says that the location is the city limits of Hamilton, where soldiers on a trek were met by their families. (However, the soldier shown has a bicycle.)
Cycle corps. - [ca. 1915] - Vintage Bicycle Photographs
Cycle corps. – [ca. 1915]
Cycle corps at physical exercises, Humber Valley. - [ca. 1915] - Vintage Bicycle Photographs
Cycle corps at physical exercises, Humber Valley. – [ca. 1915]
Cycle corps. - [ca. 1915] - Vintage Bicycle Photographs
Cycle corps. – [ca. 1915]
Trick cyclists at CNE Grandstand. - [ca. 1920] - Vintage Bicycle Photographs
Trick cyclists at CNE Grandstand. – [ca. 1920]
North Bathurst Street hill. - [ca. 1922] - Vintage Bicycle Photographs
North Bathurst Street hill. – [ca. 1922]

Photo: Alfred J. Pearson - December 6, 1924 - Bay St, showing parking, on east side, Saturday, before noon, (from Temperance St, north) - Vintage Bicycle Photographs
Photo: Alfred J. Pearson – December 6, 1924 – Bay St, showing parking, on east side, Saturday, before noon, (from Temperance St, north)

Dunlop Trophy bicycle race, CNE grounds. - [1924?] - Vintage Bicycle Photographs
Dunlop Trophy bicycle race, CNE grounds. – [1924?]
Bicycle race at Velodrome, Scarborough Beach Park. - [ca. 1926] - Vintage Bicycle Photographs
Bicycle race at Velodrome, Scarborough Beach Park. – [ca. 1926]
Bicycle race paced by motorcycles, CNE. - [ca. 1920] - Vintage Bicycle Photographs
Bicycle race paced by motorcycles, CNE. – [ca. 1920]

Start of bicycle race, CNE . - September 2, 1926. The winner of the one mile race was Bill Elder, third from left. - Vintage Bicycle Photographs
Start of bicycle race, CNE . – September 2, 1926. The winner of the one mile race was Bill Elder, third from left.
Start of first heat of schoolboys' bicycle race, CNE Grandstand. - [ca. 1926] - Vintage Bicycle Photographs
Start of first heat of schoolboys’ bicycle race, CNE Grandstand. – [ca. 1926]
Bicycle racing, Grandstand, CNE - Vintage Bicycle Photographs
Bicycle racing, Grandstand, CNE – (circa 1920 – 1940)
Finish of bicycle race, CNE. - September 2, 1926. The winner of the one mile race was Bill Elder, right. - Vintage Bicycle Photographs
Finish of bicycle race, CNE. – September 2, 1926. The winner of the one mile race was Bill Elder, right.
Cyclists lined up for race, CNE - Vintage Bicycle Photographs
Cyclists lined up for race, CNE between 1920 and 1940
Norm James in Dunlop Trophy bicycle race. - [between 1925 and 1926] - Vintage Bicycle Photographs
Norm James in Dunlop Trophy bicycle race. – [between 1925 and 1926]
Mt. Carmel Church, Reverend Stephen Anad blessing bicycle. - July 28, 1929 - Vintage Bicycle Photographs
Mt. Carmel Church, Reverend Stephen Anad blessing bicycle. – July 28, 1929
High wheel bike. - 1930 - Vintage Bicycle Photographs
High wheel bicycle, a.k.a. Penny-farthing. – 1930
Double high wheel bicycle. - 1934 - Vintage Bicycle Photographs
Double high wheel bicycle. – 1934
Dufferin Street, Eglinton to Wilson. - 1955 - Vintage Bicycle Photographs
Dufferin Street, Eglinton to Wilson. – 1955
Gold-plated racing bicycle presented to Peden, Canadian Sports Hall of Fame - Vintage Bicycle Photographs
Gold-plated racing bicycle presented to Peden, Canadian Sports Hall of Fame
HMCS "Forest Hill" crew host WRENS stationed in Halifax from Forest Hill Village, and other parts of Toronto at a dinner on the ship : Coder James Cramer (1300 Lansdowne Ave.) shows WREN Ruth Arnsby (9 Montclair) one of the bicycles sent by the Village of Forest Hill to the ship 1940-45 - Vintage Bicycle Photographs
HMCS “Forest Hill” crew host WRENS stationed in Halifax from Forest Hill Village, and other parts of Toronto at a dinner on the ship : Coder James Cramer (1300 Lansdowne Ave.) shows WREN Ruth Arnsby (9 Montclair) one of the bicycles sent by the Village of Forest Hill to the ship 1940-45
Mary J. Gilmore and Ordinary Seaman Robert Denyer try out one of the bicycles - HMCS "Forest Hill" crew host WRENS stationed in Halifax from Forest Hill Village, and other parts of Toronto at a dinner on the ship : Coder James Cramer (1300 Lansdowne Ave.) shows WREN Ruth Arnsby (9 Montclair) one of the bicycles sent by the Village of Forest Hill to the ship 1940-45 - Vintage Bicycle Photographs
Mary J. Gilmore and Ordinary Seaman Robert Denyer try out one of the bicycles – HMCS “Forest Hill” crew host WRENS stationed in Halifax from Forest Hill Village, and other parts of Toronto at a dinner on the ship : Coder James Cramer (1300 Lansdowne Ave.) shows WREN Ruth Arnsby (9 Montclair) one of the bicycles sent by the Village of Forest Hill to the ship 1940-45 – old bicycle photos
Peterson Productions filming advertisement for BIA Oil at gas station - Vintage Bicycle Photographs
Peterson Productions filming advertisement for BIA Oil at gas station – between 1950 and 1970

See more vintage photographs on the Toronto Archives website.

 

 

 

 

 

About Joel Levy 2601 Articles
Editor-In-Chief at Toronto Guardian. Photographer and Writer for Toronto Guardian and Joel Levy Photography