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Best Toronto Nightlife

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Toronto is an extremely social city. Even on the iciest nights in January, Torontonians troop out to bars, clubs and events—milling on the sidewalk outside for cigarettes, even at zero degrees. After-work hordes flock to downtown bars and patios throughout the city from 5PM, while evening carousers head to the bar at about 8PM. But things really get going by 10PM. Lines for the best Toronto nightclubs start from 10 or 11PM and sociable streets, such as Queen, are lively (and safe) till patrons spill out in the wee hours pretty much every night of the week. 

The Entertainment District is the place to go when you want to mingle with the after-work crowd, toe the dress code line, or wait it out to get into this month’s hottest megaclub. For an eclectic party crowd and the possibility of an invite to a word-of-mouth after-hours party, amble to Kensington Market. West Queen West is home to Canada’s most interesting and most cutting-edge bars. It really is the place to explore the best Toronto bars. Gay and lesbian-popular venues line Church Street in Church Wellesley and are dotted along West Queen West. If you’ve only one night in this social city, head to Ossington Street between Dundas and West Queen West and work your way down—hipster havens, cool dive bars and polished restaurants outnumber fading Laundromats, auto repair shops and karaoke rooms on the once-dodgy stretch. There’s something to suit everyone, from grungy Sweaty Betty’s and the grime chic of the Communist’s Daughter to so-hip-it-hurts Our Home. Explore and you’ll find interesting watering holes tucked in obscure corners throughout the city, premium tequila parlors, vodka dens and a whole host of such drinking and dancing destinations. Last call in bars and clubs is usually 2AM, other than on special occasions such as during the NXNE music festival.  
Crush Wine BarEd Wong

Crush Wine Bar

Neighborhood: Downtown
On a warm summer evening, the neat side patio at Crush is the perfect perch for sampling some of this cozy nook’s 400 vintages and 62 wines and champagnes available by the glass—or swirled into suitable wine flights such as Old World Hidden Gems and Mediterranean Flavours. It’s a little-known secret, but weekdays from 5 to 7PM, the British-inspired bar food menu—where you’ll find Cornish pasties, charcuterie plates and fish and chips—is 50% off. Don’t be put off by the sight of all those diners tucking into fixed price menus, you’re most welcome just to nip in for a glass of wine—or five. Like the wine list, the décor inside is tasteful—a warm, inviting room with sand brick walls and vintage wine posters. It’s a refreshingly unpretentious King Street spot—a welcome, down-to-earth change from many adjacent options.

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The Roosevelt RoomEd Wong

The Roosevelt Room

Neighborhood: Downtown
When we’re feeling especially elegant, we sashay downtown to the Roosevelt Room. The old-school, Hollywood-inspired glamour den was designed by HGTV’s Designer Guys and is a delight of Art Deco flourishes with subtle touches of technology and assured and friendly staff. It’s officially a supper club, which really just translates as rather overpriced food, a lot of pretty people, and amazing surrounds, but sometimes that’s just the ticket. While the décor is strictly 1920s, the DJs’ play list mines the last few decades and suavely swoops from Michael Jackson to Lady Gaga, keeping the crowd on the dance floor from soon after it opens at 10:30PM till 1 or 2AM. Only open on Thursday, Friday and Saturday, the food is French-ish (filet mignon mini-burgers), the dress code is strictly enforced and the crowd occasionally a tad too full of itself, but we keep coming back for the ambience.  

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The Drake LoungeEd Wong

The Drake Lounge

Neighborhood: West End
Polished to a brilliant sheen, the Drake lounge looks out onto busy Queen Street from behind gauzy, gossamer curtains, tables and chairs are studiedly cool—and the celebrities, wannabes and stylistas flock from around the city and around the world to lounge on olive banquettes and be served stiff drinks by staff who could pass as American Apparel models. The Drake lounge scene is brash, brilliant and beautiful.

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The Drake Lounge  
Mill St. Brew PubEd Wong

Mill St. Brew Pub

Neighborhood: Downtown
Friendly, sometimes frenetic, but always fun and friendly, Mill St. Brew Pub is a cavernous tavern with cheerful red-painted brick walls, 18-foot ceilings, traditional bar décor and fantastic views—the vast copper and steel tanks that the beer is brewing in. Situated in what was once the tankhouse for the Gooderham and Worts Distillery from which the district gets its name, the Brew Pub is the social heart of the district and popular with an easy-going jeans and T-shirt crowd. Beer makes its mark on a lengthy food menu, too, on dishes such as the Coffee Porter BBQ Braised Ribs, Organic Lager-marinated butter chicken and Belgian Wit Biere-steamed mussels. Avoid coinciding with the pre-theatre rush if you’re in a hurry or are hungry.

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Mill St. Brew Pub  
The Painted LadyEd Wong

The Painted Lady

Neighborhood: West End
One of the newest drinking destinations to strut its way onto the hip Ossington strip, the Painted Lady swiftly somersaulted her way over the heads of the competition and into the hearts of West End socialites. With bordello chic and a cheeky bar menu that includes now notorious white trash nachos and the succulent North Carolina-esque pulled pork sandwich, the Lady is a trump. The combination of an eclectic crowd and an eclectic entertainment bill that veers from live jazz to raunchy burlesque shows means that no two nights ever feel the same. On a hot or loud night, try and get there before 8 and grab the velvet couch beside the open storefront window—it can get smoky up front, but you’ll appreciate their sassy drinks even more with that cool breeze and when you can hear what your companion is saying.

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