Where to quench your thirst along the Ossington strip

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Once upon a time, Ossington was a forgotten street of no particular note. Today the hip west end destination has evolved into one of the city’s most exciting and vibrant corridors. These trendy spots on the strip typify what it means to party on Ossington.

Where to quench your thirst along the Ossington strip
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Bellwoods Brewery

1
124 Ossington Ave, Toronto ON M6J 2Z5

Strip away all the customary trappings and you’re left with this place where the focus is entirely on beer, and a selection that puts Toronto on par with Portland and Seattle in terms of craft status. To get your feet wet in the world of microbrews, go on one of their twice-weekly guided tasting sessions to develop your palate. If you opt out of that, they’ve got a brewpub and bottle shop where you can do your own thing.

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The Dakota Tavern

2
249 Ossington Ave, Toronto ON M6J 3A1

One part glorified basement and one part neighbourhood favourite, the Dakota is one of the best places to sip a pint and take in some fantastic live music. There’s always something going on, whether it’s the midday bluegrass brunch on weekends or the next up-and-comer gracing the spotlight. The Christmas light decorations are more charming than cheesy and the floor-level stage lends a living room atmosphere.

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The Painted Lady

3
218 Ossington Ave, Toronto ON M6J 2Z9

Know what goes well with a pint of beer? A burlesque show, that’s what. There’s always the option of either live music or a DJ (depending on which night you go). The name is inspired by New Orleans’ dive bars and the framed pictures of infamous but anonymous ladies of the night. The down-to-earth easygoing vibe and cheaply-priced drinks make this one of Ossington’s most-loved watering holes.

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Reposado Bar and Lounge

4
136 Ossington Ave, Toronto ON M6J 1R5

Reposado means Spanish for “restful” and it reflects the atmosphere inside, from the cozy candlelit patio to the chill live jazz on select nights. Tequila is by far the most popular drink here with an incredibly diverse selection, but the beer options stand up strongly in their own right. It also goes without saying that you must indulge in tapas as they’ve got mouth-watering options that go with any drink.

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Union Restaurant

5
72 Ossington Ave, Toronto ON M6J 2Y7

This spot manages an upscale-meets-easygoing atmosphere, with a gourmet menu that is locally and seasonally sourced. Local eating is so important here that the Union crew built their own smokehouse in Grey County. If you’re not that hungry, Union has a charming bar area where you can nurse a beverage. Make sure you take a look at the extensive wine list.

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