This Novellahood is my hood. Ossington is a strip of pure hipster madness, which has its ups and downs (the pretentiousness is real, but so are interesting bar concepts and cool boutiques), but if there’s one thing you can count on here, it’s that you’ll never experience a dull moment in this corner of the city. Spend a day, spend a night, and have a blasty-blast with the help of my personal guide to Dundas and Ossington!
As a connoisseur of mochas, I can attest that Sam James’ mocha is the absolute best in the whole wide city. The recipe (which I won’t disclose here) is so simple, but so genius. TRY IT. Hot or iced. Of course, everything else they make here is perfect, too, from the lattes to the conversation.
This diner has been here for so long I’m pretty sure it qualifies as a historic site. I love this place because it has that classic diner feel without being too gritty, the food is good and nicely priced, and they have MAD drink specials ($4 mimosas, all day, every day!). They’re also open 24 hours, so feel free to come here for a burger in the middle of a drunken night.
If any of my friends ever have a birthday, it is celebrated here. Why? Because Get Well is not only a bar, but it’s also an arcade and has an in-house North of Brooklyn Pizzeria. Most of the vintage arcade games are free to play, so you can challenge yourself to a game of Dig Dug with a drink in one hand and a slice of pepperoni pizza in the other.
Being inside this Canadiana shop feels like chanting Oh Canada and drinking maple syrup while riding a moose that’s wearing a Mountie uniform. Check it out if you want to bring home some cool, all-Canadian stuff.
‘Tis the season for play-watching, and this theatre has all your nostalgia planned out for the summer: buy your tickets to Rocket Man: The Music of Elton John, Always Abba, Buddy: The Buddy Holly Story, Mary Poppins and other gems.
The shop window displays are always so cute, it’s nearly impossible not to step inside this tiny shop. They sell the perfect blend of girly-girl and hip, and the clothes never lack in both imagination and sophistication. Find your next wedding season dress here, or a punchy statement piece for your summer festival-going.
This is a Dundas and Ossington go-to. Even if you’re not a fan of beer, Bellwoods Brewery is always a good time. I personally love this place because on holidays, when the LCBO and Wine Rack are closed, Bellwoods is usually open, and my drinking plans are saved.