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Established in 1944 as "The Pilot Grill", our original location was at 800 Yonge Street, on the west side, just north of Bloor Street. The Pilot's distinct name was meant to be a tribute to the heroic flyers of World War II.
After the war ended in '45, The Pilot became known as an artists' bar and was a favorite hang-out for the Spadina Eleven and a host of artists from nearby Isaac's Gallery and Carmen Lamanna down the street. The Pilot remained a steady presence through the sixties as Yorkville developed into the hub of Toronto's hippie community. 1972 brought the move to our present location at 22 Cumberland Street, just one block north. Legend has it that when the actual move took place, a group of Pilot regulars physically carried the classic Art Deco-style bar around the corner to its new home. The current owners are a group of fanatic Pilot loyalists who bought the bar in 1987. It has been their mission to retain The Pilot's original personality and charm, while introducing new features to keep pace with the times. Our rooftop patio, The Flight Deck, opened in 1993 and is the largest "patio with altitude" in Yorkville. The Pilot's second floor is home to The Stealth Lounge, a sophisticated party space complete with its own bar, café tables, bench seating and a stage with a PA system for a live band or other performers. The Stealth Lounge can be booked for private parties from 30 to 130 people. Over the past two decades, The Pilot has been a well-known home for live jazz in the city. We feature Canada's finest jazz musicians and international artists every Saturday afternoon.
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