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![]() Ossington Avenue in the Queen-Dundas stretch is sizzling hot as Toronto's "it" destination with some of the city's most hipster spaces, bars and restaurants. Sure, venues are intimate but they're HUGE on character! Starting at Dundas and heading south, check out the following digs available for private or semi-private gatherings. Choose one and host, or string them together for a very kicky drink-dine around along a very happening strip: The Lakeview Restaurant Dine at both tables or use them as food-cocktail stations with guests mingling in the generous aisles in between. Or, consider a fun networking round as guests move from booth to booth for ice-breaking conversations and brainstorming. Total capacity is 130 with patio for 30. 1132 Dundas St. W., www.thelakeviewrestaurant.ca
Jezebel Burlesque The adjacent private Boudoir Parlour — high-back banquettes and smoked mirror ceiling — smoulders with exclusive VIP potential for up to 30. Play up the venue’s back alley entrance for themed meet-and-greets. Current total capacity is 90. 227 Ossington Ave., www.jezebeltoronto.com ![]() The Painted Lady Oh what a time awaits at this off-the-wall bordello-esque bar where kitsch meets outrageous fun. Staff often shows up in costume – Sailor Moon recently manned the bar – and the energy verges on Coyote Ugly spontaneity. Dripping chandeliers, exposed brick and jewel-tones complement the richness of a solid mahogany bar and sexy New Orleans-style front parlour that opens to itty-bitty wrought iron patio. Strip out furnishings for additional elbow room. Corner stage at back. Total capacity is 111. 218 Ossington Ave., www.thepaintedlady.ca
Reposado The intimate space (30 maximum) is easily re-configured for stand-up receptions. A salvaged stained-glass cathedral window adds gorgeous behind-the-bar focus and elegant glassware are part of the aesthetic detailing. Find additional privacy in the lovely cantina-style patio oasis out back with room for 36. 136 Ossington Ave., www.reposadobar.com ![]() Rolly’s Garage An open-concept main floor has staging potential, while an upstairs mezzanine offers dj-audio-visual work space. Driveway frontage accommodates spillover till 11 pm. Stand-up capacity is 150. Special occasion permit required. 124 Ossington Ave., www.rollysgarage.com
Watusi Wall art featuring ’60s pop icons (Hello Marilyn!), classic drinks, shared platters and a 1958-’78 audio sparks a cool hang-out-and-settle-in ambience. Semi-private lounge area seats 10 under the lava lamp. Total capacity is 50 sit-down. 110 Ossington Ave., www.watusi.biz ![]() LeVack Block Cross over to the “dark side” — the back room — where black draping, concrete floor and neon art emanates an “underground” vibe. Both spaces are easily configurable to crowd and staging. Total capacity is 222. 88 Ossington Ave., www.levackblock.com ![]() Union Rustic accents marry well in an arty farm mural, barn-board flooring, brick and salvaged wallpaper. A marble-topped horseshoe-shaped bar greets at the entrance giving way to seating (clear-out for stand-up receptions of up to 80) and open kitchen with ringside chef’s table seating for six. Seating capacity 35. 72 Ossington Ave., 416-850-0093 ![]() Lennox Contemporary The street-level front room fits 100. Steps up to back gallery area doubles that number plus provides entry to a funky 40-seat black-box theatre. Leave art up or replace with own visual components. Make a catering connection with Oyster Boy — gallery owner is a partner. 12 Ossington Ave., www.lennoxcontemporary.com
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