Summertime in Toronto is when the city really comes alive. And as it turns out, it’s been that way for quite some time.
Although newer additions like Taco Fest, Caribana, or even grabbing a drink on a rooftop patio are things only enjoyed by more recent Torontonians, other summertime activities like the CNE, spending a day at the beach, or taking a dip in a City pool have been around for decades. And there are the photos to prove it.
Toronto History has an archive of old photos of the city that give us a glimpse into what life was like way back in the day. And as cool as it is, it’ll also leave you wondering how people in the early 1900s survived the summer here in long dresses and full suits.
So get ready to take a step back in time with these 20 vintage photos of summertime in Toronto from the early 1900s to the 19070s.
CNE Midway – 1904

Alexander Galbraith/Toronto History
Cricket at Upper Canada College – 1908

Alexander Galbraith/Toronto History
Parkdale Canoe Club – July 1911

Arthur Goss/Toronto History
Kew Beach – July 1915

Arthur Goss/Toronto History
Boys playing in the falls at Humber River – June 1923

John Boyd/Toronto History
Pillow fight at The Police Games – July 1929

John Boyd/Toronto History
Sunnyside swimming tank – July 1929

Arthur Goss/Toronto History
The Whip at Hanlan’s Point – June 1930

Alfred Pearson/Toronto History
CNE Warrior’s Parade – August 1930

John Boyd/Toronto History
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Northeast corner of Macdonnell and Queen – August 1935

Arthur Goss/Toronto History
Sunnyside wading pool – July 1936

John Boyd/Toronto History
The back of 119 Oak Street – June 1936

Arthur Goss/Toronto History
Davenport Road, looking west from Howland Avenue – July 1953

Howard McDonald/Toronto History
Night dance at the Don Mills Shopping Centre – June 1955

Gilbert Milne/Toronto History
Keeping cool on Painswick and Cairnside crescents – June 1968

J. Stunden/Toronto History
Crowds on the CNE grounds in front of the Horticulture Building – August 1974

Harvey Naylor/Toronto History
Scarborough softball game – August 1975

Peter Mykusz/Toronto History
School-themed float in Canada Day parade – July 1976

Peter Mykusz/Toronto History
Foot race at Birchmount Stadium – July 1977

Toronto History
Overhead view of CNE grounds – August 1972

Harvey Naylor/Toronto History