Are You Cool Enough For Ossington?

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There comes a time in every downtowner’s life when they slow down to reflect whether they’re hip enough to start hanging out in Ossington. It happens to be general knowledge that Ossington – (Oss) oozes with cool and therefore anyone who dares to walk the strip must also possess some type of west end cred.

While I can neither confirm nor deny this, I want to clear the air and let you know that Oss is not just for bloggers and people of athleisure.

Ossington is that one pretty girl who often gets judged by her looks but really just wants you to know that she’s more than that. She also has a pretty sweet personality and she’s read like 6 books in 2017.

Here’s a few reasons you should check out Ossington:


Food & Drinks

Cote De Boef 

130 Ossington

Possibly my favorite restaurant in the city – which is interesting because it’s a butcher shop first. Cote de boef supplies the neighbourhood with quality cuts and products by day but come sunset, the shop transforms into the city’s coziest bar a vin!



80 Ossington

Though Oss is pretty far from Greek town, we don’t feel the pinch with Mamakas around. This spot made me love lamb chops and practically bathe in Dodonis feta. Ooh and the smelts – feed your Bumble date some smelts. Unless you don’t like them, then please head to Pizza Pizza.



90 Ossington

Oddseoul is so damn delicious, I don’t even know where to begin! A Korean and American fusion snack bar right smack in the middle of Oss. You need to try some Bulgogi cheese steak, it will get your life sorted out.



88 Ossington

If you’re feeling the bouj a little, just head to Omaw – where they use phrases like “Tasting Menu” and “Foie Gras”. The southern style menu is the trek, they also managed to stock the beverage program with North American ONLY beee and wine as well as some V. nice selection of Bourbon.



Bobbie Sue’s Mac and Cheese

162 Ossington

First of all, I’m getting hungry writing this and seriously contemplating ordering some mac and cheese. I just want you to know that. Bobby Sue’s alone is a MAJOR reason to go to Ossington. Toronto’s only mac and cheese restaurant – more like a shack but if you’re gonna be shackin’ up anywhere, you may ask well do it at Bobby Sue’s and stuff yourself with some good eats!


Bang Bang Ice Cream

93a Ossington

Trends (*cough cough charcoal) come and go but they always come back to Bang Bang. And who can blame them? With ridonculous flavours like Cinnamon toast, Burnt Toffee, London Fog, Matcha – Tiramisu – save the blaming for another day.




Bellwoods Brewery

124 Ossington

Bellwoods is Ossington’s unofficial street patio. A real gem in the summer months but still pretty amazing in winter. The resto/bar is spacious but somehow still feels cozy inside and the bottle shop right next door is all too convenient. The crowd is fun and hip and good looking.  I’ll see you there?


The Dakota Tavern

Or more affectionately called Dakota is where I’ve had the best random nights. My friends and I have stumbled in on weeknights and discovered a number of amazing artists. The Dakota never disappoints. I would also be rude if I don’t tell you about their Bluegrass Brunch. You eat brunch while listening to live Bluegrass bands – it’s simple, it’s loud, it’s fun – just like the crowd.

Baby Huey’s

If you want a dance party, I’ll give you a sweaty fun dance party. Head on over to Baby Huey’s and join the trendy and very tipsy West Queen West crowd. Don’t wear layers here, you’ll get sweaty but what you should wear are your dancing shoes because the back of the house likes down and dirty beats. I’m into it. Bring $5 for cover.

Oak Island

121 Ossington 

I’ve been really into Oak Island’s real Miami Vice vibe lately. It’s a whimsical little spot across the street from Baby Huey’s. Heavy on the whimsy here with drinks like Watermelon Sundae (Vodka, Midori, Strawberry Kiwi soda) and Cream Soda (Dark Rum, Turbinado, Vanilla bean, Herb Soda). Another nod to Ossington’s fun variety.




So there, I think you’ll find that this little guide is enough proof that Ossington is in fact as cool as it gets but so are you! So get westbound and check out this ever evolving strip. You never know what you’ll find – bring a toque, just in case.












Shiela is the original Small Girl and the Founder/Content Editor of Small Girl Medium City. She spent the majority of her "Grown Up" life in Toronto and reluctantly calls it the 6ix. Connect with her on Instagram - @shylo_l and Twitter - @sgmc_to; Definitely say hi when you see her on the mean streets!

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