Rare Vintage Postcards Capturing Toronto in the Late 1850s

These rare vintage postcards offer a fascinating glimpse into Toronto around 1858-1859, a period of rapid growth and transformation. The images capture the city’s early streets, public buildings, waterfront, and daily life at a time when Toronto was emerging as an important urban center in Canada.

With their historical detail and quiet atmosphere, these early views preserve a valuable visual record of the city more than 160 years ago, revealing both its modest beginnings and its developing character.

King Street, Toronto, Ontario, circa 1858-59

Masonic Hall Buildings, Toronto, Ontario, circa 1858-59

Mechanics Institute and St. James Parochial School, Toronto, Ontario, circa 1858-59

Normal School Buildings, Toronto, Ontario, circa 1858-59

Provincial Exhibition Building, Toronto, Ontario, circa 1858-59

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How NOT to Drive in Toronto

When cars first appeared in Toronto in the early 1900s, there were few regulations and very limited driver education. Most drivers had no formal training—they just bought a car and hit the road. Predictably, accidents became more common as more people tried to figure out how to drive in real time.

Traffic laws were either minimal or completely ignored. Speed limits were set ridiculously low—around 8 to 10 mph in city areas—but drivers regularly broke them. Pedestrians and horse-drawn vehicles still dominated the roads, which meant constant clashes between the old and new modes of transportation.

Streetcars ruled many of the main routes in Toronto, and early car drivers had to deal with tracks, frequent stops, and passengers hopping on and off. Many didn’t handle it well—cars would try to weave around streetcars and end up smashing into them or the curbs. Streetcar vs. automobile collisions became a regular event.

Here’s a selection of 20 vintage images of bad driving in Toronto from the early 20th century. All photos from from the City of Toronto Archives collection.

Damaged automobile, Ontario Street, ca. 1909

Crowd looking over fence at wrecked automobile in ditch, south side of Dupont, east of Christie, ca. 1910

Electric car accident at Glen Road Bridge, 1912

Crowd looking at electric automobile in accident on Glen Road Bridge, 1912

Automobile on muddy Morley Avenue, 1912

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The First Miss Toronto Contest, 1926

The Miss Toronto beauty pageant mural is located on the building at 1249 Queen St W, home to The Rhino Bar & Grill, in the Parkdale neighborhood of Toronto.

Jean Ford Tolmie was crowned the winner after competing against over 65 hopefuls in the contest’s inaugural year. The 1926 pageant was held at Sunnyside Bathing Pavilion in front of a crowd of 30,000, where Jean was crowned with flowers. The pageant was later moved to Exhibition Stadium & Grandstand in the mid-1930s.

The pageant became a focal point for discussions about modern and traditional Toronto womanhood, as seen in the essay “Is the Flapper a Menace?,” or “Miss Toronto, Delight, and the Making of the Modern Toronto Girl.” The pageant was abolished in 1991.

The August 26, 1926 edition of the Toronto Daily Star featured this ad.

40 Fascinating Photos of the Toronto Transit Commission in the 1980s

The Toronto Transit Commission (TTC) is the public transport agency that operates bus, subway, streetcar, and paratransit services in Toronto, Ontario, Canada, some of which run into the Peel Region and York Region. It is the oldest and largest of the urban transit service providers in the Greater Toronto Area, with numerous connections to systems serving its surrounding municipalities.

Established as the Toronto Transportation Commission in 1921, the TTC owns and operates four rapid transit lines with 75 stations, over 150 bus routes, and 9 streetcar lines. In 2022, the system had a ridership of 577,941,400, or about 2,104,200 per weekday as of the fourth quarter of 2022.

The TTC is the most heavily used urban mass transit system in Canada. These fascinating photos were taken by Kevin Mueller that show the Toronto Transit Commission in the 1980s.

Toronto TTC, Humber Loop, August 1983

Toronto TTC CLRV 4069 Exibition, August 1983

Toronto TTC PCC 4500, Bathurst St. Bridge, August 1983

Toronto TTC PCC interior, August 1983

Toronto TTC PCC on St. Clair, August 1983

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Bob Dylan’s “Blood on the Tracks”: The Story of the 20-Year-Old Who Accidentally Shot an Iconic Album Cover

Paul Till has never met Dylan, but he did shoot the profile image that appears on the cover of Dylan’s perhaps most beloved album: Blood On The Tracks. More impressively, he was only 20.

Blood on the Tracks album cover.

“I was 20 years old at the time, and had been doing photography for about three years and had been using a darkroom for a year and a half or so. I loved the darkroom and learning and using various darkroom techniques. I was also a big Bob Dylan fan, and so when the 1974 tour was announced, there was a mail-in “first-come first-served” process for getting tickets to his show at the Maple Leaf Gardens in Toronto. I took my letter down to actual post office where their post office box was and ended up with quite good tickets. I was directly stage right a few seats from being obstructed by loudspeakers. I was relatively close to the stage, but not really close. I photographed the 2nd of Bob Dylan’s two concerts in - I think it was - January of 1974. I’d never photographed a concert before.

“The camera I was using was a screw-mount Leica III which dated back to the 1930s. It was my dad’s, he’d bought in London in 1945. I had a fast normal lens for it, but not a telephoto, so I borrowed a Canon 135 f3.5 lens from the father of a friend of my sister. Anyhow, I shot about a roll and half of 35mm Tri X - the standard 400 ASA film of the time - and tried to figure out the exposure. I pushed the film to about 1600ASA (ASA is the same as ISO. but that’s what it was called then). I don’t recall if I did the darkroom work to make the cover image in the Fall or Winter of 1974.

“At the time, I was doing a lot of darkroom manipulation of photographs as well as hand-coloring them. I was very familiar with Bob Dylan’s music and I felt that the combination of darkroom technique and hand coloring echoed the old/new dichotomy of much of his work, as well as the notion that it echoed the (sometimes slapdash) off-handed power of his words and music.

“Here’s how it was actually made: The negative was enlarged in the darkroom onto another piece of film in such a way that just Dylan’s head was on it. This would normally result in a positive image on the film which, if you printed it onto a piece of photo paper, would give you a negative print. However, I solarized this piece of film (that is, re-exposed it to light) as it was being developed. This partially reversed the image and also gave it the distinctive line between what was dark to start with and what has made dark by the solarization. Technically, this technique is actually called “the Sabbatier effect”, and the lines are called “Mackie lines”. This resulted in a quite dark and low-contrast piece of film to make a print from. I had to use the very high-contrast grade 6 Agfa Brovira paper to get a print with enough contrast.”

The original photo which the Blood on the Tracks album art is based on.

Later that year, Till decided on a whim to send Dylan his photos. “I looked up his address in Who’s Who at the library,” Till said, and proceeded to mail a few images. “I thought maybe I’ll get a letter from him saying thanks or something.” Instead, he received a letter from Dylan’s art director, Ron Coro. “They said, your picture has been selected for use on the album cover,” Till recalled. He received just $300 in payment. “But the Canadian dollar was worth more then. So I came up with a little less than $300.”

Not much of a payday from having your name credited on one of the greatest damn breakup albums of all time, but the experience did change Till’s life for the better. At the time, he’d been mulling over career options and wanting to write poetry. After his photo graced Blood On The Tracks, “I thought, you know what? Maybe I should be a photographer. You can’t make any money writing poetry.”

Till has no idea where the original print is. He’s convinced Columbia may have lost it. And he still hasn’t met Dylan, but a friend of his went backstage at a later show and mentioned the image to Dylan. According to this friend, Dylan responded kindly: “Tell him it was a good picture!”

30 Fascinating Then and Now Photos Capture Yonge Street, Toronto in 1954 and 2014

Yonge Street is a major arterial route in the Canadian province of Ontario connecting the shores of Lake Ontario in Toronto to Lake Simcoe, a gateway to the Upper Great Lakes.

Yonge Street, Toronto in 1954 and 2014

Once the southernmost leg of provincial Highway 11, linking the provincial capital with northern Ontario, Yonge Street has been referred to as “Main Street Ontario” and (including the Bradford-to-Barrie extension) is 86 kilometers (53 mi) long.

In Toronto and York Region, Yonge Street is the north-south baseline from which street numbering is reckoned east and west. The eastern branch of the subway Line 1 Yonge–University serves nearly the entire length of the street in Toronto; it serves as the spine of the Toronto subway system, linking to suburban commuter systems such as the Viva Blue BRT.

Yonge Street is a commercial main thoroughfare rather than a ceremonial one, with the Downtown Yonge shopping and entertainment district containing landmarks such as the Eaton Centre and Yonge-Dundas Square.

These fascinating photos from Howard of Yonge Street, Toronto in 1954 and 2014 that show how this street has changed for 60 years.

 83 Yonge Street, Toronto, 1954-2014

85-87 Yonge Street, Toronto, 1954-2014

207 Yonge Street, Toronto, 1954-2014

243 Yonge Street, Toronto, 1954-2014

271 Yonge Street, Toronto, 1954-2014

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Cycling in Toronto in the Early 20th Century

The omnipresence of the bicycle and bike culture in 1890s Toronto far surpasses anything we know today. But remarkably, the political issues associated with cycling are almost unchanged.

In the 1890s Toronotonians were preoccupied with the question of ‘scorchers’: those riders who traveled too quickly, ignored rules of the road, and endangered pedestrians. Similarly, there was a concerted effort to improve the quality of the city’s streets for cyclists. The ‘Good Roads Campaign’ argued that city council needed to set aside more money to pave roads for the benefit of the bike rider. Though, unlike today, their priority was to make suburban roads more bike-friendly to allow for people to leave the city easily on weekends.

Finally, cyclists successfully courted political power. Candidates for both the mayoralty and council made a point of wooing the biking lobby, often showing up at meetings of cyclists to expound upon their respective platforms. If there was an important question in Toronto, the bike unions were sure to be involved somehow.

By the end of World War II, however, the cycling heyday was over. Cycling as something like a movement, or aspect of civic consciousness, or popular sport, didn’t really return until the 1980s, and gain serious momentum in the 2000s.

Cycling club in Toronto, 1900

A leisurely ride Jarvis Street, 1903

Bay Street, 1907

Boys cycling across Lakeshore Road bridge at Mimico, 1907

Walking it up the hill to St. Clair, 1907

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40 Amazing Vintage Photographs That Show What Toronto Looked Like in the 1900s

Toronto in the 1900s didn’t much resemble the city we know today. Not only was the skyline virtually undeveloped—the tallest structures were the Temple Building at 10 storeys and the Trader’s Bank Building at 15 storeys—but the Bloor Viaduct was yet to link the east and west sides of the city.

In the 1900s, Toronto had a population of approximately 210,000 people, horses and carriages were still common on city streets, and the city suffered one of the worst fires in its history, losing almost all of the main commercial district (bounded by Bay, Wellington, Yonge, and Front Streets).

Here’s what Toronto looked like through the 1900s:

King Street, 1900

Board of Trade Building, 1900

Cycling club, 1900

Weston Train Station, 1900

Eaton’s factory interior, 1901

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The Bloor Viaduct During Construction Through Amazing Photos

The Prince Edward Viaduct System, commonly referred to as the Bloor Viaduct, is the name of a truss arch bridge system in Toronto, Ontario, Canada, connecting Bloor Street East, on the west side of the system, with Danforth Avenue on the east.

The Bloor Viaduct during construction

The system includes the Rosedale Valley phase (a smaller structure, referred to as the Rosedale Valley Bridge, carrying Bloor Street over the Rosedale Ravine) and the Sherbourne Phase, an embankment built to extend Bloor Street East to the Rosedale Ravine from Sherbourne Street. The Don Valley phase of the system, the most recognizable, spans the Don River Valley, crossing over (from west to east) the Bayview Avenue Extension, the Don River, and the Don Valley Parkway.

The roadway has five lanes (three eastbound and two westbound) with a bicycle lane in each direction. The subway level connects Broadview Station in the east with Castle Frank and Sherbourne Stations to the west.

This selection of pictures, taken during the construction of the Bloor Street East viaduct (1915-1917), comprises some of the images in the Canadian Historical Picture Collection, housed in the Special Collections department at Toronto Reference Library.

Pier D. Training... First Construction...

Break in Sheeting. East End N2. Pier D

Don in Flood

Don Sec. East Approach

Don Sec. Pier B. Forms

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22 Incredible Photos Show the Aftermath of the Great Fire of Toronto in 1904

It was a miserably cold night, with bitter gusts of wind and a light snow even though it was the middle of April. And about an hour after sunset, things would get even worse. No one is entirely sure what caused the blaze. It might have been faulty wiring. Or a stove. But around 8 o’clock on that terrible night of April 19, 1904, a constable walking his beat in downtown Toronto spotted the first flames rising out of a necktie factory on Wellington Street just west of Bay (where the black towers of the Toronto-Dominion Centre stand now). As the officer rushed to sound the alarm, the flames spread quickly.

The aftermath of the Great Fire of Toronto (1904)

Within an hour, every firefighter in the city was desperately trying to contain the blaze. But they were losing the battle. Violent gusts of wind blew the water from their hoses off course. The spray froze in mid-air, coating everything with ice. Thick tangles of newly-installed telegraph, telephone and electrical wires made it impossible for ladders to reach the flames. Textile factories, book-sellers, paper supply companies and chemical manufacturers crowded the core of the city — they provided the perfect fuel. The firefighters were being blinded by smoke. The fire chief broke his leg, falling from a ladder. The April snow was joined by a constant rain of burning wood, broken glass, and ash.

The flames tore through the heart of the city, moving south from Wellington all the way down to the Esplanade and east toward Yonge. Twenty acres of downtown Toronto — more than a hundred buildings — were on fire. You could see the glow of the flames for miles in every direction.

Mayor Urquhart sent urgent telegrams to other cities asking for help. And all through the night they came: firemen from Hamilton, London, Peterborough, Niagara Falls and Buffalo joining the fight. Within a few hours, there were two hundred and fifty of them pouring millions of litres of water on the flames. At the Evening Telegram offices on Bay Street, employees spent hours spraying water out the windows to save the building. At the Queen Hotel (which stood about where the Royal York does now), guests and employees organized bucket brigades, hung water-soaked blankets out of the windows and beat off the flames, saving the hotel and helping to stop the fire's advance before it could cross Yonge Street.

Finally, not long before sunrise, nearly nine hours after it had started, the fire was out. One hundred and twenty-five businesses had been destroyed. Five thousand people were put out of work. More than ten million dollars worth of damage had been caused. Somehow, amazingly, no one had died.

The ruins smouldered for two more weeks, with smaller fires popping up and reigniting from time to time. The charred husks of the damaged buildings were dynamited and the rubble cleared out of the way. That’s when the Great Fire claimed its only life.

Looking south from south of King St. West, between Yonge St. & York St.

Bay St., east side, between Wellington & Melinda Steets, showing shop of H. F. Sharpe & Co., photographic goods

Bay St., east side, looking south from north of Wellington St. West

Bay Street looking north from just north of Front Street

Front and Yonge, with what's now the Hockey Hall of Fame on the right

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