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Where to eat and drink in Toronto: Ossington Avenue

November 21, 2019

By Dick Snyder

About 10 years ago or so, Ossington Avenue was a very different place. There were no of-the-moment restaurants and bars, no yoga studios, no gourmet coffee joints, no cool boutiques... not even a vinyl (record) shop. It was just Ossington Avenue back then. Not, as it's known today, the "hip Ossington strip." But we love Ossington today, even though the gas station and tire shop (where I used to get my tires) are both gone. (Sad.) But I'm ok driving a little further for car service. Now I've got my favourite record shop (Rotate This!), my favourite place for buck-a-shuck oysters (Boehmer), one of my favourite wine bars (Paris Paris), one of my favourite pizzerias (Libretto)... you get the picture.

No rose-coloured glasses here! We love what Ossington Avenue has become and we love all the amazing bars and restaurants that have made it their home. Here are a few notables. Some of them are newer, some older, some we visit on our tours, and some we just visit for our own enjoyment.

If you're a visitor to the city or a local, Ossington is always worth a trip. It's ever-changing and ever-evolving. Just don't drive there on a weekend evening. You won't enjoy that one bit. So let's go north to south and check out a few spots... 

Band playing at Dakota Tavern.
Jessica Stuart takes the stage at the Dakota.

The Dakota Tavern

Coolest. The Dakota is a pure rock, rockabilly and country bar. Live music almost all the time. Cheap cover, cheap beer, etc. This is where you'll find top local musicians hanging out even if they aren't performing. Sunday is the best no-bullshit brunch in the city, with bourbon chicken waffles and beer from Junction Craft. And a $9 Ceasar to beat down that hangover. There's even a kids' menu.

Vibe: Basement chic. It's downstairs.


Paris Paris

Not actually on Ossington, but just a minute west along Dundas. Paris Paris has nothing to do with Paris and doesn't look at all Parisienne. But it's open all day and has 1/2 price wine specials in the afternoon (by the bottle) and the steak tartare is one of the best in Toronto.

Vibe: Casual/hip. More on the casual. Woody and bright and open and fun. Easygoing. Here's a hint for the guys: women hang out in wine bars.

Pizzeria Libretto

Good frickin' pizza. Good effin' wines. Nice bar. Great staff. Good for an evening out. An extensive menu of pastas and snacks. You can't go wrong at Libretto.

Vibe: Elegant casual. Is that a thing?


Boehmer Restaurant

Paul Boehmer is the nicest guy. He's also one of Ontario's pioneering farm-to-table chefs. This is a guy with the right attitude. He makes top-notch dishes with local produce and doesn't wave his spoon around declaring that he's the best. Oh, but he is the best, actually, having "reigned supreme" over celebrity chef Susur Lee on Iron Chef Canada this fall. Well, no matter. We loved him before. Boehmer is where we go for pristine Ontario lamb, delicate Nova Scotia scallops, great (great!) steak tartare. And we'll let you in on a little secret: Tuesdays. Why Tuesdays? Buck-a-shuck and $25 lobsters and 1/2 price bottles of wine. All day. Don't tell anyone! Oh, and the cocktail are amazing.

Vibe: Beautiful and elegantly lit, with wooden chandeliers and killer artwork. Wide open space with a great big bar and lots of wood. Comfortable and worth a linger.

The Painted Lady

The Painted Lady is the kind of place you stumble upon and never want to leave. Forget eating. There's no food. But the cocktails are killer, the beer is local and great, and the scene is superbly humanistic. You might have burlesque dancers shimmying across the bar. Or a wicked-ass DJ spinning nothing but Prince and the folks who worshiped him. Or an insane trio of alt-punk. Or death metal. Or Tom Jones. You just don't know.

Vibe: Awesome.


Superpoint Pizza

One of the city's top pizza take-out joints by day, cool Italian pasta restaurant by night. Good, honest food and a nice wine list. Superpoint is run by some of the same people who are behind Paris Paris.

Vibe: Like a nice Italian trattoria.


Meaty Argentinian fare, with lots of grilling and marrow. This place will fill you up. Excellent selection of global wines and very good cocktails.

Vibe: Woody and dark and warm and good.

Cote de Boeuf

Côte de Boeuf

Just enough French attitude here, delivered in a Toronto-esque style. You'll see. Côte de Boeuf is a butcher shop and wine bar, open all day for grocery shopping and drinking (and eating, if you must). Excellent steak tartare. Interesting and smartly chosen wines by the glass or bottle. Very expensive very good meats and poultry for sale.

Vibe: Urban Parisienne. You expect to hear French, but you don't.


The sister to Côte de Beouf. So expect the same, but with ... uh.. huh. No, expect the same, but slightly larger and without meat hanging in the front. The bar is horseshoe-shaped, just like Le Petit Fer à Cheval in the Marais district in Paris. The food is about as good as it gets.

Vibe: Cozy and urban, French-style.

Sweaty Betty's

A legendary dive bar and one of the first of the new wave of business to make Ossington Avenue their home more than 10 years ago. Local beers and no-nonsense cocktails. Always great banter at the bar. Great music too: Sweaty Betty's has a cool jukebox.

Vibe: Cozy and dark, decorated with discarded couches and furniture. Check your chair carefully before you sit.

Discover Ossington with us! Come on a tour. We'll introduce you to the coolest people and places. When you book, tell us you want to discover Ossington and we'll make it so. We can visit anywhere from 3 to 5 places on a tour. Just let us know what you fancy!