Dundas East Before It Was Dundas East

Dundas is one of the weirdest streets in Toronto. And one of the oldest, too. The guy who founded our city, John Graves Simcoe, ordered it built all the way back in the 1790s. It heads west from Toronto for a couple hundred kilometers — and it also, of course, winds its way through the middle of our city in complete defiance of our grid system.

Part of the reason Dundas doesn't follow the same layout as most of the major thoroughfares in Toronto is because it didn't actually start out as one street at all. The original Dundas — built by Simcoe so troops could move through the province quickly in case of an American invasion — only reached as far east as what's now the intersection of Queen & Ossington. That spot was near the military reserve that once surrounded Fort York. It wasn't until after the First World War that Dundas was extended through Toronto by cobbling together a bunch of smaller streets.

One of those smaller streets was Wilton Avenue. It ran east from Yonge (beginning at the southern end of what's now Yonge & Dundas Square) all the way east to the Don Valley and across it to a spot just beyond Broadview. That's Wilton in the photo above, getting a facelift in the spring of 1912. That spot is just west of Sumach Street — it's completely unrecognizable today, in the middle of Regent Park.

A few blocks to the west of there, between Jarvis and Sherbourne, Wilton took a gentle curve. It was called Wilton Crescent for that bit. And you can still see the curve on Dundas today. It's where Fillmore's Tavern is.

Here it is getting new streetcar tracks in June of 1911:

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Sean Marshall tells a more complete history of Dundas on Spacing here. And Chris Bateman does the same for blogTO over here. You can see what the curve on Dundas looks like today on Google Maps here.

I used one of the city workers in the photo at the top of this post as part of the design in my dream postcard for the artist Kathleen Munn. You can check that out here.