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Drink
Ossington is a tad scuzzy around the edges, though tentacles of hipster hangouts extend northward from gentrifying Queen Street. At the crossroads where gallerygoers mingle with day-pass patients from the Centre for Addiction and Mental Health, Sweaty Betty’s (13 Ossington Ave, 416-535-6861) is a suitable citadel—a dark and brooding bar with a killer jukebox. Add in the swingers who slip into and out of Wicked (1032 Queen St West, 416-669-5582), a storefront sex club, and you get a sense of the clash of clandestine thrills on offer. Welcome to a new kind of Emerald City.
Drinking carries on until 2am and the legal age is just 19, so stamina—and pacing—is key. Order a microbrew pint of Creemore Ale at Crooked Star (202 Ossington Ave, 416-536-7271) and perch on the patio, or sip from the city’s largest selection of tequilas at Reposado Bar & Lounge (136 Ossington Ave, 416-532-6474). The Dakota Tavern (249 Ossington Ave, 416-850-4579) is a subterranean saloon with an alt-country ambience—think barn-board walls and barrel bar stools. The live music is equal parts roots and twang, and gets groovers shaking to local acts like Luke Doucet. Sunday brunch is served at communal tables, with live bluegrass accompanying the flapjacks and eggs.
