Many Toronto streets do one thing really well, but Ossington does it all, making it the perfect avenue to spend an entire day wandering through (bonus: it’s also one of the coolest streets on the planet). The sweet spot is the Ossington strip between Queen St W and Dundas St W, where you’ll find tons of indie shops and trendy restaurants door-to-door. Here’s an offbeat guide on how to spend a perfect day on Ossington Ave.
Head over first thing in the morning. Skip the car and take the 501 Queen or 505 Dundas streetcar, or ride the 63 Ossington bus from Ossington Station and start your exploration near Queen St, then wander north as the day unfolds.
Begin your day at a minimalist caffeine stop. Rooms Coffee (135 Ossington Ave) is a local fave for sipping and lingering before the street gets busy. If you like your espresso with a side of classic charm, head to I Deal Coffee & Wine (162 Ossington Ave). The space is super cozy, with vintage chairs and church pews, making it the perfect spot for people-watching.
Ossington is built for browsing, so you can easily pop in and out of some of the most amazing indie storefronts while supporting local businesses. Explore hidden clothing gems like Lost & Found (12 Ossington Ave) for elevated menswear and high-end basics, Reigning Champ (41 Ossington Ave) for premium sweats, Annie Aime (42 Ossington Ave) for top French brands like Saint James and Jack Gomme, and I Miss You Vintage (63 Ossington Ave) for designer consignment.
For the most perfect Pilates-maxxing outfits, head to Permission (127 Ossington Ave), then stop by Kotn (148 Ossington Ave) for ethically and sustainably made basics.
Of course, your Ossington soiree won’t be complete without a pit stop at the legendary Uncle Studios (46 Ossington Ave). The space was founded in 2019 by local Toronto creator Allegra Shaw and her friend Shirin Soltani, and blends minimalist fashion with ’70s nostalgia (and the prices are super-friendly). Bonus: the space has a true analog photo booth parked inside! For $10, you’ll get a classic four-pose strip developed the old-school way (so you can browse the racks while you wait for your pics to develop).
If you want a classic Ossington lunch, head to the Michelin-recommended Pho Tien Thanh (57 Ossington Ave) for authentic Vietnamese dishes. The menu is at least 90 items long, but a hot bowl of pho hits the spot here (bonus: the space has candy-floss pink walls that are super charming). Or visit Union (72 Ossington Ave) for an afternoon drink and Canadian-French fare made from local ingredients.
On warmer days, ease onto a patio with a beer in hand at Bellwoods Brewery (124 Ossington Ave), or go agave-forward at Reposado (136 Ossington Ave) for tequilas, Mexican tapas and live music!
Before a proper sit-down dinner, roam through a few more indie shops. For old-school vinyl, Rotate This (186 Ossington Ave) sells new and classic releases of vinyl records and CDs, while Hobbiesville (9 Ossington Ave) has the best trading cards and anime-related items. Telegramme Prints & Custom Framing (194 Ossington Ave) is the place for impulse-buy posters and limited edition art prints (like this floater-frame quilt made of a bunch of pairs of pants, with the oil on canvas part sewn onto it). And the shop offers much more than posters and framing, it also hosts rotating exhibitions! A few stops away, Memento Film Lab (216 Ossington Ave) has a dedicated gallery space and hosts regular community events featuring local photographers.
For a late-afternoon caffeine jolt, visit the (soon-to-open) Japanese matcha darling The Matcha Tokyo: it’s locked in 139 Ossington Ave as its first North American location!
And because you’ll likely need a sweet treat before dinner, head to Bang Bang Ice Cream & Bakery (93A Ossington Ave). The shop has the most inventive ice cream sandwiches on house-made cookies, cups, cones and in to-go tubs! Try flavours like Burnt Toffee Fior di Latte, topped with sponge toffee and saucy burnt sugar, or go all out and get two tasty flavours scooped into a warm rolled egg waffle.
For dinner, this is where the street really starts showing off. Depending on your vibe, head to Soos (94 Ossington Ave) for modern Malaysian street food, Neon Tiger (108 Ossington) for Pan Asian and Indian dishes or La Banane (227 Ossington Ave) for stylish, French-influenced cuisine. Azhar Kitchen & Bar (96 Ossington Ave) is all about Middle Eastern influences with local ingredients, all prepped in a state-of-the-art wood-fired oven (on Mondays, don’t skip the $10 martinis), and then check out Fallen Feather (217 Ossington Ave) if you’re aiming for one last cocktail that turns into two or three.
Bar Libretto (221 Ossington Ave) is a must-see! The original Pizzeria Libretto space has shifted toward the neighbourhood’s late-night crowd: there’s now a twice-daily happy hour (from 4 to 6 pm for the early crowd and again from 9 to 11 pm), weekend DJs and a rotating lineup of guest bartenders from across the city!
If you’d prefer to grab a meal to-go, head to The Golden Dragon (214 Ossington Ave). It’s being hailed as the most authentic Irish-Chinese spot in Canada and one of the best spots in the city for a proper spice bag.
For late-night crowds, end the night at Bowie (180R Ossington Ave). It sits beneath a laundromat (with a back-alley entrance), but serves the most delicious cocktails and snacks until 2 am. Or head to The Painted Lady (218 Ossington Ave.) for a burlesque show in a cheeky saloon!
After exploring Ossington, spend a perfect day in this unexpected neighbourhood that was recently named Toronto’s ‘coolest’.
