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, layouts (even wonder why there's an upper and lower Gerrard St.?), nor 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.
Rent a Zipcar or hire an Uber and meander 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.

strange streets toronto

Wellesley Cottages
The prettiest cul-de-sac on this list (and perhaps in all of Toronto), Wellesley Cottages is strange for its beauty and history. Entering this place is like walking into a time warp back to 1880s Toronto. This little community near St. James Town is a collection of workers' cottages that have been immaculately preserved, and if you don't know where to look for them, you won't find them.

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.

Edgewood Ave.
This is a private street and one that's just a bit more weird than others like Percy St. or Melbourne Place. The northern extension of Edgewood Avenue north of Eastwood Road climbs up a hill, winds around a series of row houses, and seems like no other place in Toronto, complete with a healthy dose of signs warning that this is private property.

What did I miss? Add your nominations for the strangest streets in Toronto to the comments.

Photo of Craven Road by jer1961 in the blogTO Flickr pool.


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