Raise a glass to these historic Toronto bars

Toronto’s historic bars and taverns have become legends in their own right thanks to their iconic architecture and infamous clientele. Toast the city’s storied past and down a pint or two at some of the city’s oldest watering holes.

Wheat Sheaf Tavern

667 King St W, Toronto, ON M5V 1M9

This longstanding tavern at the southwest corner of King and Bathurst dates back to 1849 (18 years before Confederation) and was once a favourite watering hole for soldiers from the nearby garrison at Fort York. A sloping French-style mansard roof sits atop the handsome redbrick building, which stands in stark contrast to the nearby glass condo towers. Now surrounded by hip eateries and trendy nightclubs, the King Street tavern still keeps its Old World feel with heavy wooden tables and a well-worn jukebox, although there are plenty of modern big screens and tasty chicken wings to appease modern-day clientele.

Pilot Tavern

22 Cumberland St, Toronto, ON M4W 1J5

The name behind this enduring bar pays homage to the heroic RCAF flyers of World War II. The local haunt once served as a meeting place for Yorkville’s creative community of artists, musicians and writers. When the bar relocated from its original Yonge Street site to its current spot on Cumberland, a group of regulars carried the wooden bar by hand to its new home. The sprawling upper level rooftop patio (the Flight Deck) seats 185 people and attracts a mix of tourists, nearby office workers and Bloor Street shoppers.

The Horseshoe Tavern

368 Queen St W, Toronto, ON M5V 2A2

Opened in a former blacksmith shop (hence the “Horseshoe” moniker) this legendary tavern has first opened back in 1947. The bar had dubious reputation back then thanks to some unsavoury regular customers such as famous bank robber Edwin Alonzo. The Queen Street haunt was converted into a live music club in the mid-1950s and has attracted Canadian and international acts like Blue Rodeo, Our Lady Peace, Bryan Adams, Willie Nelson, the Police, The Ramones and many more.

The Black Bull

298 Queen St W, Toronto, ON M5V 2A1

Not just a prime patio space, this Queen West stalwart lays claim as one of the oldest pubs in the city. Founded in 1833 (or perhaps 1838, depending on who you ask), the Black Bull was a popular pit stop for farmers travelling to the city centre from the west. Today, the local landmark attracts long lineups in the summer months thanks to its cheap pub fare and in-demand outdoor seating. The building has undergone numerous renovations over the years but some unique architectural details have been preserved, including the mansard roof and yellow-brick pilasters (flattened pillars) on the exterior.

Gladstone Hotel

1214 Queen St W, Toronto, ON M6J 1J6

This boutique hotel might be known for its contemporary art shows and avant garde rooms, but there’s plenty of history within these walls. The local landmark dates back to 1889 and is the city’s oldest continually operating hotel. The lobby Melody Bar retains a number of Victorian architectural details — such as frescoed faux-marble pillars and dramatic arched windows — and serves up classic vintage cocktails that’ll bring you back in time, if only for the night. After a tipple or two, be sure to take a ride in the hand-operated elevator — one of the last of its kind.

The Fairmont Royal York

100 Front St W, Toronto, ON M5J 1E3

Tucked away inside the historic Fairmont Royal York Hotel, this storied bar is a welcome respite from the hustle and bustle of the downtown core. The intimate space features Edwardian-style drapery, dark wood-paneled walls and sumptuous armchairs. The leather-bound drink list features a wide selection of fine single malt whiskeys and signature cocktails inspired by Canadian literary icons. If you’re not in the mood for booze, opt for Afternoon Tea service and enjoy finger sandwiches and scones served on pretty china plates.

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