craven road toronto

The 5 strangest streets in Toronto

The strangest streets in Toronto are ones you might stumble upon and feel like you were in some different city, temporary lost while still broadly at home. They're not the ones with the weirdest names or necessarily filled with random odd houses, but in terms of general ambiance, this collection will thoroughly defamiliarize you.

Here are my picks for the strangest streets in Toronto.

Craven Rd.

You have a fence on one side, a mess of old and new homes on the other, and just that vibe, that weird vibe that is Toronto at its most odd and wonderful. No one planned this place; it built its character over time. Craven Road might be the most interesting street in Toronto.

strange streets toronto

Redway Rd.

Head down this hidden hill that terminates at an old sewage treatment plant. It's best at night in the fall when cars kicks up the leaves strewn across the road and headlights illuminate the tree canopy. This is one of the hardest hills for cyclists in Toronto.

strange streets toronto

Wellesley Cottages

One of Toronto's prettiest cul-de-sacs, Wellesley Cottages is strange for its beauty and history. Entering the place is like walking into a time warp. This little community near St. James Town is a collection of workers' cottages that have been immaculately preserved. Exploration is discouraged because the lane is private property.

strage streets toronto

Blackburn St.

I love Blackburn St., but it has this profoundly unfinished feel to it. Overlooking the Don Valley and a Toronto Hydro substation, the houses here are a smattering of old cottages and anonymous new structures. The hodgepodge character here is everything that most Toronto streets are not - and the complete opposite of planned developments.

convair driveConvair Dr.

Curling around Pearson Airport, Convair Dr. has a unmistakably mysterious feel to it. Everything feels forbidden here, from the old security gates to the ILS equipment at the side of the road. The road cuts across airport property, but is open to the public. Just don't park here.

Lead photo by

Jeremy Gilbert 


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