What Toronto looked like in the 1960s

Toronto in the 1960s was a city caught between what it had always been and what it was quickly becoming. Buildings were going up, old ones were coming down, and the streets were full of the noise and energy of rapid growth. New apartment towers rose over quiet residential blocks, subway lines pushed further into the city, and immigrants arriving from around the world were reshaping entire neighbourhoods. At the same time, familiar storefronts, taverns, theatres, and corner shops kept their hold on daily life — at least for a little while longer.

King Street in the early 1960s was still very much the financial heart of the city. The Prince George Hotel anchored one corner, while the curved facade of the William H. Wright Building — then home to The Globe and Mail — defined the other. The Canadian Bank of Commerce Building loomed in the background, its stone mass typical of the institutional architecture that lined King and Bay Streets.

The Prince George Hotel, originally built as the Rossin Hotel in 1856, stood at the southeast corner of King and York Streets until its demolition in 1969. In its final years it remained a working hotel with entertainment in the Pyramid Room. The Royal York Hotel is visible in the background, its towers still dominating the skyline near Union Station.

Yonge Street in the early 1960s was one of the most densely packed commercial strips in the country. Between Dundas and Gerrard, nearly every address held a tavern, a clothing store, a cinema, or a record shop. Many of these buildings have since been demolished, their facades sometimes retained as thin skins on new developments, but the street life they contained is gone entirely.

At Yonge and Dundas, the Brown Derby Tavern occupied the northeast corner. It claimed Canada’s longest bar — 114 seats — and its basement lounge was decorated in a Gay Nineties theme. A Globe and Mail news ticker ran along the rooftop. Just to the south, the Biltmore Theatre seated 929 people. After it closed in 1986, the building became an informal flea market before eventually being absorbed into the Metropolis complex, now called The Tenor.

A few blocks north of Dundas, the stretch of Yonge near Gould Street was packed with entertainment and retail. Sam the Record Man and A&A Records faced each other across the same block, with Steele’s Tavern wedged between them. Gordon Lightfoot played his early shows at Steele’s. The iconic spinning neon records that would later define Sam’s exterior didn’t appear until 1971. Today the entire block is the Ryerson Student Learning Centre.

The block between Gerrard and a few addresses south contained some of the most visually striking signage on the entire street. The House of Mann featured plank siding and a rooftop carriage. The Bermuda Tavern’s vertical neon sign advertised it as the ‘home of the steer.’ The Edison Hotel at 335 Yonge offered ‘Dancing Nightly.’ Most of these buildings were demolished around 2010.

Further south along Yonge, the Ryrie Building at the corner of Shuter Street housed the Silver Rail Restaurant and Cocktail Bar on its ground floor. The Colonial Tavern, sandwiched between two flagship bank buildings near King, was a key venue in the city’s jazz scene, regularly hosting touring acts from the United States. Above it all, the Imperial Theatre served audiences for decades.

The Spadina Roundhouse and the John Street Roundhouse were two of the most industrial features of the downtown landscape. Both sat just west of the financial core, surrounded by rail lines and freight corridors. The Spadina Roundhouse, operated by Canadian National Railway, was demolished in 1986. The CPR’s John Street Roundhouse survived and is now part of the Steam Whistle Brewery complex.

The TTC was the circulatory system of the city. Streetcars ran along routes that are now bus lines, and the subway system was still young — the University line opened in 1963, replacing the Dupont streetcar east of Christie Loop with the 4 Annette trolley bus. GO Transit launched its commuter rail service in 1967, with trains running out of Scarborough crossing the St. Clair Avenue East grade crossing in the service’s first few months of operation.

Yorkville, by the mid-1960s, had become the centre of Toronto’s counterculture. Coffee houses and folk venues lined the blocks near Avenue Road and Yorkville Avenue. The Purple Onion was one of the most well-known of these venues, drawing performers and audiences from across the city and beyond. The neighbourhood was home to artists, musicians, and activists, and it stood in sharp contrast to the corporate development happening elsewhere downtown.

Little Italy on College Street was another neighbourhood with a strong identity of its own. Bar Italia had already become a fixture by the mid-1960s, its presence reflecting the concentration of Italian immigrants who had settled along College Street between Manning and Clinton. Similar patterns were visible across the city — immigrant communities establishing institutions, businesses, and cultural anchors in specific neighbourhoods.

New City Hall opened in 1965 and immediately changed the look of the downtown core. Designed by Finnish architect Viljo Revell following an international design competition, its two curved towers and saucer-shaped council chamber at Nathan Phillips Square were unlike anything else in the city. The old City Hall — a Romanesque Revival building from 1899 — remained standing just to the east.

The Carlton Tower at the northeast corner of Yonge and College, built in 1960, featured a distinctive patterned concrete screen that wrapped the parking structure above street level. The clock that once sat on the building is long gone. A 73-storey, 250-metre tower has since been proposed for the site. On the waterfront, the city’s port was still an active industrial zone — marine terminals, the Redpath Sugar Refinery, and broad commercial wharves occupied what would later become Harbourfront.

The CNE remained one of the most attended annual events in the city throughout the decade. The 1968 fair featured the Flyer roller coaster, the Alpine Way midway ride, the Wild Mouse, and the ‘Laff in the Dark’ dark ride. Canadian National Railways’ steam locomotive #6213 sat on display beside the Toronto Marine Museum. The Shell Tower provided aerial views over the entire grounds.

Residential streets across Toronto had a quiet, settled look. Rows of brick homes on tree-lined blocks in East York, the Beaches, and the older Annex-area streets showed a city where single-family housing still dominated large portions of the urban fabric. Families built new homes on Pharmacy Avenue just south of Lawrence, children played in wading pools at Withrow Park, and residents skated at outdoor rinks in winter.

The Don Valley ski hill at Lawrence Avenue and the Don Valley Parkway drew skiers from across the city. Rope tows made from thick rope pulled skiers to the top of the hill. It was a modest operation by any measure, but it served a genuine recreational need for Torontonians who didn’t have the means to travel further north.

At Danforth Technical School in 1968, a group of students made local news when they walked out to protest the school’s ban on miniskirts. Students who continued wearing them were threatened with suspension. The story made the papers, with photographs capturing the students on the street — a small but telling moment in a decade when cultural rules were being tested across the city.

Aerial photographs from the late 1960s reveal how much of Toronto’s industrial and rail infrastructure still occupied prime land close to the lake. Fort York sat surrounded by rail lines and yards. Exhibition Stadium was visible from above. The Gardiner Expressway cut east-west through the lakefront. Don Mills, photographed from the air in 1968, showed a planned suburban neighbourhood at full build-out, its curvilinear streets and cul-de-sacs a deliberate contrast to the grid of the older city.

By the end of the decade, Toronto’s skyline was noticeably different from what it had been in 1960. The TD Centre’s first tower was complete. New apartment buildings had gone up across midtown and the inner suburbs. Whole blocks in the older city had been cleared for development. The Riverdale Zoo still operated in the east end, ferries crossed to the islands, the Santa Claus Parade drew crowds every November, and Maple Leaf Gardens remained the undisputed centre of hockey life — but the city around all of it was changing fast.