Cocktail barWine and cocktail$$$the-annexTue-Sun 17:30-22:30
Dreyfus on Harbord is the Annex's reference cocktail and natural-wine bar since 2018, chef Zach Kolomeir's small-plate kitchen under 50 seats.
Signature drink: Mediterranean spritzes, Beaujolais by the glass
Food: Mediterranean snacks and pasta
Order: A spritz and the cured fish board.
Tip: Closed Mondays. Sister to Bar Mordecai on Dundas West. The chairs at the bar take walk-ins.
Cocktail barCocktail bar$$ossingtonTue-Sun 17:30-02:00
Pinkerton's Snack Bar on Gerrard East is the city's reference snack-and-cocktail dive since 2017, owner Marc Baglio's pan-Asian plates and drinks.
Signature drink: House cocktail rotation
Food: Pan-Asian snack bar
Order: A house cocktail with the bao buns and crispy rice.
Tip: Walk-ins only. Closed Monday. Late nights to 02:00 Friday and Saturday.
Cocktail barDive bar$$ossingtonDaily 16:00-02:00
The Communist's Daughter on Dundas at Ossington is the strip's reference dive bar since 2003, a former Portuguese diner with low ceilings and cheap beer.
Signature drink: Beer and a shot, well drinks
Food: Bar snacks
Order: A pint of local lager with a shot of rye.
Tip: Cash preferred under $10. Late kitchen has frozen pizzas after 22:00.
Cocktail barTiki bar$$$ossingtonWed-Sun 17:00-02:00
Miss Thing's on Queen West in Parkdale runs Polynesian tiki cocktails and Pacific Rim plates since 2013, the painted bamboo interior the strip's reference.
Signature drink: Mai Tai, Tiki classics
Food: Pacific Rim small plates
Order: A classic Mai Tai with the salt-and-pepper squid.
Tip: Closed Monday and Tuesday. Weekend nights take walk-ins after 22:00 only.
MexicanDive bar$little-italyMon-Tue 11:00-03:00, Wed-Thu 11:00-04:00, Fri 11:00-04:30, Sat 09:00-04:30, Sun 09:00-03:00
Sneaky Dee's at College and Bathurst runs the city's reference late-night Tex-Mex kitchen until 04:30 on Friday and Saturday nights since 1987.
Signature drink: Pitcher of cheap lager
Food: Tex-Mex, King's Crown Nachos
Order: The King's Crown Nachos with a pitcher of Stella.
Tip: Cash only at the till; debit card at the bar. Late-night kitchen the city's most reliable after-bar option for nachos.
Cocktail bar$$$little-italyMon-Thu 16:00-01:00, Fri-Sat 16:00-02:00
Bar Pompette on College Street is the aperitif bar above Pompette since 2018, North America's 50 Best Bars ranked #8 in 2026 with a low-ABV cocktail program.
Order: The signature Pompette Spritz or whatever the bar is pouring on draft.
Tip: Reservations through Tock. The downstairs Pompette is the restaurant; bar is upstairs.