2019 marked the 75th birthday of The Pilot Tavern, an occasion worth celebrating in a joint that's seen a lot of celebrations. The Pilot was born "The Pilot Grill" in 1944 at its original location 800 Yonge Street, just north of Bloor. The name of the bar was a tip of the cap to the heroic RCAF flyers of World War II.

During the Yonge Street era, The Pilot was a clubhouse, meeting place and sacred temple to artists, musicians and writers. The Spadina Eleven hung out here, Austin Clarke was inspired, Julie Christie awed. In those days The Pilot often cashed the artists' cheques from the nearby Issacs Gallery and the Carmen Lamanna Gallery just up the street. Lightfoot performed and Dylan met Robbie Robertson to recruit the Hawks as his back-up band here too.

In 1972 The Pilot moved to its current location at 22 Cumberland Street. Legend has it that a group of Pilot regulars physically carried the original bar top around the corner to its new home. A sense of history and occasion was carried over too.

In the late 70’s, laughs and ideas were shared amongst the likes of Martin Short, John Candy, Catherine O’Hara and other fellow SCTV cast members as they frequented The Pilot’s backroom. After a breakout performance by The Tragically Hip in the summer of 86’ celebrations took place at The Pilot and it was finalized that they would be signed to their first recording contract; the start of their long illustrious career.

1987 brought new, enthusiastic owners made up of Pilot fanatics who had been patronizing the establishment since their high school days at nearby Jarvis Collegiate. They vowed to retain the essence of what made The Pilot a truly great Toronto bar while also introducing some new traditions. In 1993 The Flight Deck opened, a rooftop patio with The Pilot's trademark laid-back vibe and a new ingredient: sunshine. The Pilot's second floor is home to The Stealth Lounge, a romantically dark and inviting event space that hosts parties of all sorts. As we have for the past 3 decades The Pilot still offers live Jazz from some of Canada's finest musicians every Saturday afternoon. Over the years The Pilot has hosted parties and partnered with TIFF, The Jazz Festival, BBDO, Fife House, just to name a few.

The Pilot has stood the test time and continues to stay relevant in an ever changing neighbourhood and city. From humble beginnings to one of the most sought after rooftop patio bars in the city. For The Pilot, business is the consistency and loyalty of our customers that have been coming here for years and we hope to continue that legacy.



Menus Reserve Phone Call Locations
items in bag