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 for artists, musicians and writers. This iconic restaurant made its mark in Bloor-Yorkville for nearly 75 years with its Flight Deck rooftop, eclectic menu, and live jazz nights. Back in the day artists, writers & musicians hung out at the spot. During the Yonge Street era, The Pilot was a clubhouse, and meeting place for artists, musicians and writers.
The restaurant has been around the city streets of Toronto since it opened in 1944 at its original location on Yonge Street. It’s a catchy clever name The Pilot, and was a tribute to those who fought in World War II. After the war, it became a favourite hang-out for local artists, and the bar remained popular through Yorkville’s transition to a hippie community. It was in 1972 that the Pilot moved to its present location – 22 Cumberland Street, in the heart of Yorkville. According to legend, some of the Pilot’s regular customers carried the original bar to the new location. 
<<BELOW – a new version of The Pilot>.     In 1987, the current owners took possession of the popular spot, and have kept it true to its original charm. They introduced to the “Flight Deck”, one of the largest rooftop patios Toronto has to offer. They have also introduced the “Stealth Lounge”, a more sophisticated party space, that can be rented out for parties ranging in size from 30 to 130 people. The Stealth Lounge offers its’ own bar, complete with comfy lounge seating. The food selection is average, but the food itself is quite good. I have never personally had any problems with food or service. And for being in one of the trendiest neighbourhoods in TORONTO, it is very unpretentious.