Exclusive, Neighbourhood Guide

Neighbourhood Guide: How to spend a day on Ossington Ave

Via Toronto RentalsVia @pilotcoffee on InstagramVia Porter Re:viewVia Mamakas Taverna

There aren’t many better spots to explore in Toronto than Ossington Avenue. This strip of street has become a mainstay for shopping, food, and drinking since some intense gentrification made it over. Let’s spend a day on Ossington Ave together, shall we?


Part of Trinity- Bellwoods, this street has become a destination in its own right. It’s one of the top stops in the West End, so we’ve picked out a few places you definitely need to stop by.

Firstly, it’s breakfast time! Let’s stop by Pilot Coffee Roasters (117 Ossington Ave) for our fix. We recommend cold brew and avo toast. Also, we recommend taking a minute to appreciate this gorgeous space, which has been featured by Design Lab for their outstanding design!

pilot coffee

Ossington has wicked shopping, so let’s go spend some dollars. Stop by Victoire Boutique (129A Ossington Ave) for chic finds with a vintage feel. Also, definitely top by Reigning Champ (41 Ossington Ave) for minimalistic branded goodies, all made in Canada.

Worked up an appetite trying on 8 different hoodies? Perfect. Let’s head to La Cubana for some snacks. By snacks, we mean cuban sandos and plates that are guaranteed to hit the spot.

la cubana

Now, the afternoon sun is (hopefully) upon you, so let’s spend some time chilling in Trinity Bellwoods Park (790 Queen St W). It’s only a couple blocks away and it’s the perfect place to relax, play frisbee, catch an outdoor movie, or peruse a farmer’s market.

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Dinner time! The best time! Stop by Mamakas Taverna (80 Ossington Ave) for shared meze plates. This seriously fresh Greek food will hit the spot without weighing you down too much for our next pick…


Feeling like some dessert? Well, you’re lookin’ like a snack so we aren’t surprised. Head over to Bang Bang Ice Cream (93A Ossington Ave) to bang bang a cone into your mouth. Their flavours are just the right amount of not boring, and there are TONS! Try banana pudding, London Fog, burnt toffee, or lychee rosewater raspberry.

ice cream

Time for a nightcap? You’re in the right place! Get cozy at The Dakota Tavern (249 Ossington Ave) for three things, as stated by the sign on the front door. “Beer, Music, Whisky.” Say no more!

Feeling full, shopped out, and pleasantly buzzed? That’s the effect a day on Ossington Avenue has on people. Until next time!