Here’s your chance to explore Toronto the way your ancestors saw it, one street at a time, on a map web application, called Old Toronto, that was released this week.
Using more than 30,000 historic photos from the City of Toronto Archives, Sidewalk Labs has recreated Old Toronto.
Clicking on a photo on the city map pulls up information about the photo, including (when available) the title, date, condition, and any copyright restrictions.
Search feature
You can search for a specific address, but keep in mind addresses may have changed over time. You can also search by the name of a street, building, such as city hall, or perhaps a business, although that turned out to be hit and mostly miss.
A search of Eatons produced a number of photos that spanned a few decades. A few were of the store. The majority were not. Searching for bank or Royal Bank of Canada produced a lot of photos, but again I couldn’t figure out why the keywords triggered those results. Loblaws also produced a number of bizarre results with nothing in the descriptions to indicate why the keyword found those photos.
Sticking to the street name proves to be the most effective means of finding relevant photos, especially for the impatient researcher.
One of my ancestors, Alexander Brown Young, lived on King Street East near Sumach in the 1920s. Clicking on photos in the area gives me a sense of what the neighbourhood looked like when he lived there. To narrow down the location, I first looked for the address on Google Maps. The Toronto City Directories are also helpful when trying to narrow down where a specific address was located. Use the reverse look-up toward the back of the directory in later years to look up a street. That will tell you where the closest cross-streets are.
Another feature on Old Toronto allows users to share the photos on Facebook and Twitter, or save the link to share with a friend by email. To save the photo to your computer, simply right-click with your mouse on the image and select Save as in the drop-down menu.
Over time, Sidewalk Labs plans to add more images from both the city archives and other repositories. They are also building an aerial button that will enable people to see how the city has changed from a bird’s-eye view, in addition to street view.
Old Toronto is inspired by web applications developed for San Francisco and New York.

I wish I had someone there! That would be so fun.
I found a lot of misplaced photos, but it was great to have a look at old Toronto like this.
I found a few wonky bits too, but it is certainly great fun.
Is this initiative taking photos from the public? I have a good photo of my grandfather standing in front of his tailor shop at 1388 Queen Street in 1905.