$$$$
Cocktail barOssington
Bar Mordecai on Dundas West is a retro Wes-Anderson cocktail room since 2020, World's 50 Best Discovery list with vintage and modern drinks.
OrderThe Mordecai Martini, served with house olives.
TipNo reservations; small room fills early on weekends. Closed Sunday-Tuesday.
$$$$
Cocktail barLittle Italy
Track & Field on College Street is the lawn-games cocktail bar that returned in October 2021, two floors with bocce, shuffleboard and a photo booth.
OrderA round on the bocce court with a tapped cocktail.
TipWalk-ins or Tock reservations for the bocce lanes; 30ft bar runs through the main floor.
$$$$
Cocktail barPintxo barLittle Italy
Bar Raval on College runs vermouth on tap and Spanish bar snacks from a mahogany Art Nouveau counter since 2015, Grant van Gameren's room the Michelin Bib.
OrderA vermouth on the rocks with a slice of jamon iberico.
DrinkVermouth on tap, manzanilla sherry
FoodPintxos and Spanish snacks
TipWalk-ins only. Arrive before 17:30 for an easy stool; the doors open at 13:00 every day of the week.
$$$$
Cocktail barSpeakeasyThe Annex
Civil Liberties on Bloor at Ossington runs a no-menu speakeasy since 2014, bartenders mixing drinks to your taste in an industrial-vibe back room.
OrderTell the bartender three flavours you like and let them mix.
DrinkDealers' choice, bartender-led
FoodBar snacks only
TipNo menu by design. The door at 878 has no signage; ring the bell. Late nights until 02:00.
$$$$
Cocktail barCocktail barKensington Market
Cocktail Bar on Dundas West is Jen Agg's drink room since 2013, the menu split seasonal, bold, citrusy, liquor forward and wild cards, sister to Grey Gardens.
OrderWhatever the bar manager David Greig is excited about that night.
DrinkSeasonal cocktail rotation
FoodSnacks from Grey Gardens sister kitchen
TipClosed Mondays. Snacks from Grey Gardens kitchen run light. Bar seats walk in; tables on Resy.
$$$$
Cocktail barModernist cocktail barQueen West
BarChef on Queen West is Frankie Solarik's modernist cocktail bar since 2008, theatrical drinks with dry ice, smoked glass domes and botanical foams.
OrderThe signature smoked Manhattan presented under a glass dome.
DrinkSmoked Manhattan, Abstract Ice
FoodBar snacks only
TipReservations recommended; cocktails run $25 to $50. Closed Monday.