Click here for an interactive map of Toronto’s Archive.

Today, I spent hours time-travelling through the streets of Toronto.

I saw a parade at Yonge and King at the end of the Boer war in 1901, men raising their bowler caps in the air and waving Union Jack flags under three-storey storefronts advertising coal and furs and Union Pacific tickets.

I saw streetcars, horse-drawn wagons and bicycles navigating the same intersection in 1912, with the help of a police officer directing traffic while wearing a bobby helmet.

I saw the streetcar right-of-way on St. Clair as it appeared in the early 1900s, surrounded by grass and gravel in the centre of the road. I saw the aftermath of an explosion in Rosedale, a fire up near Weston Rd. and 401, an accident investigation into a police officer’s death under the “Keele Street Subway” in the Junction. I saw open farm fields in Willowdale in the 1950s.

And bars: the old Pilot Tavern and the Colonial Tavern on Yonge, the separate entrances for “Gentlemen” and “Ladies and Escorts” at a bar in south Riverdale in the 1970s. And bombs, piled up and stored on the sidewalks of Liberty St. during the First World War.

This was the entrancing and often surprising experience of exploring Google’s newly launched “Old Toronto” map of historical photos, made by their Sidewalk Toronto labs and launched last week at oldtoronto.sidewalklabs.com. Overlaid on a Google Street map of Toronto today, dots mark the spots of 30,000 historical photos from the Toronto Archive.

These photos, part of the Toronto Archive’s collection of 1.7 million, are among the 100,000 that have so far been digitized by the city. In a note on the site, Sidewalk Labs promises they will be adding more, and that the project will be open-source, with open data available to developers who want to use it to create other applications or versions of the map.

This is a bit of a side project for Sidewalk Labs in Toronto, who are working with the city to redevelop a section of the waterfront as a new “smart city” — possibly, I’ve seen some speculate, an attempt to earn brownie points with residents who have been expressing concerns about privacy and democratic control over that redevelopment process. Maybe so. But either way, it’s a bit of a gift.

Looking through it is a history lesson, but it feels more like flipping through a shoebox of old family photos. A single dot on the map at a downtown location like Yonge and Queen will reveal dozens of photos, taken at different points, different perspectives. Right now, it has a kind of random feel: other than by location, there’s no organizing principle, and some tiny side streets have many photos while some large stretches of main roads have almost none.

But the mishmash is fun and surprising to flip through: different generations of cars and streetcars and buildings; people on the streets in the fashions of various generations, from black and white to Kodachrome colour to familiar recent digital resolution, all showing shots of places that have changed so much but often feel so familiar.

It ain’t perfect yet, that’s for sure. Many of the shots in Scarborough when I looked were just misplaced on the map — a bunch of them were of the Horticulture Building at Exhibition Place and another bunch were the Church of the Holy Trinity that should be behind the Eaton Centre. The shots have been placed on the map using an automated geocoding process that relies on the descriptions in the captions, and obviously this creates room for error. There’s a function asking people to report errors, and suggest the correct locations. Over time, it should be more accurate.

But at a first exploration, this actually became kind of fun — as disappointing as it was to click a location I know well, hoping to see what it looked like back in history, and instead see photos that obviously came from somewhere else, it also added a bit to the serendipitous feel of the whole exploration.

And serendipity is what the whole experience of the site feels like.

A massive country estate at Yonge and Wilson (1930), the blaring multi-coloured MUNTZ MUNTZ MUNTZ MUNTZ record store sign at Yonge and Dundas (1975), the black-and-white, giant, surprisingly sturdy, bridge at the Toronto islands that may be from 1896.

From childhood memories to distant history and right up to the near-contemporary, some of it mundane, some of it odd, some of it fascinating.

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The photo archives of the city are a treasure. This mapping site offers an interesting new way to explore them. I spent a few hours longer looking around than I planned, strolling through time. Time well spent.

Ed Keenan is a columnist based in Toronto covering urban affairs. Follow him on Twitter: @thekeenanwire

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