Cocktail bar$$$little-italyMon-Thu 16:00-01:00, Fri-Sat 16:00-02:00
Bar Pompette on College Street is the aperitif bar above Pompette since 2018, North America's 50 Best Bars ranked #8 in 2026 with a low-ABV cocktail program.
Order: The signature Pompette Spritz or whatever the bar is pouring on draft.
Tip: Reservations through Tock. The downstairs Pompette is the restaurant; bar is upstairs.
Cocktail bar$$$ossingtonWed 18:00-00:00, Thu 18:00-01:00, Fri-Sat 18:00-02:00
Bar Mordecai on Dundas West is a retro Wes-Anderson cocktail room since 2020, World's 50 Best Discovery list with vintage and modern drinks.
Order: The Mordecai Martini, served with house olives.
Tip: No reservations; small room fills early on weekends. Closed Sunday-Tuesday.
Cocktail bar$$little-italyWed-Thu 17:00-00:00, Fri-Sat 17:00-02:00, Sun 16:00-23:00
Track & Field on College Street is the lawn-games cocktail bar that returned in October 2021, two floors with bocce, shuffleboard and a photo booth.
Order: A round on the bocce court with a tapped cocktail.
Tip: Walk-ins or Tock reservations for the bocce lanes; 30ft bar runs through the main floor.
Cocktail barPintxo bar$$$little-italyDaily 09:00-02:00
Bar Raval on College runs vermouth on tap and Spanish bar snacks from a mahogany Art Nouveau counter since 2015, Grant van Gameren's room the Michelin Bib.
Signature drink: Vermouth on tap, manzanilla sherry
Food: Pintxos and Spanish snacks
Order: A vermouth on the rocks with a slice of jamon iberico.
Tip: Walk-ins only. Arrive before 17:30 for an easy stool. Open from 09:00 for the coffee crowd.
Cocktail barSpeakeasy$$$the-annexDaily 17:00-02:00
Civil Liberties on Bloor at Ossington runs a no-menu speakeasy since 2014, bartenders mixing drinks to your taste in an industrial-vibe back room.
Signature drink: Dealers' choice, bartender-led
Food: Bar snacks only
Order: Tell the bartender three flavours you like and let them mix.
Tip: No menu by design. The door at 878 has no signage; ring the bell. Late nights until 02:00.
Cocktail barCocktail bar$$$kensington-marketTue-Sun 18:00-02:00
Cocktail Bar on Dundas West is Jen Agg's drink room since 2013, the menu split seasonal, bold, citrusy, liquor forward and wild cards, sister to Grey Gardens.
Signature drink: Seasonal cocktail rotation
Food: Snacks from Grey Gardens sister kitchen
Order: Whatever the bar manager David Greig is excited about that night.
Tip: Closed Mondays. Snacks from Grey Gardens kitchen run light. Bar seats walk in; tables on Resy.