The Pilot

The Pilot is a beloved, proudly LGBTQ+-owned Toronto staple, an aviation-themed tavern that's anchored Yorkville since 1944 and moved to its current Cumberland Street home in 1972 (regulars famously helped carry the original Art Deco bar around the corner by hand). Spread across a ground-floor bar and dining room, a private second-floor event space, and the beloved rooftop patio "Flight Deck," it serves laid-back, satisfying pub fare, burgers, sandwiches, and classic dishes, alongside more than a dozen drafts and well-made cocktails. Its rooftop is consistently ranked among the city's best, drawing a loyal following for golden-hour views and Saturday afternoon jazz matinees, and its calendar includes a lively LGBTQ+ drag brunch. A genuine piece of Toronto history that's kept its soul while staying thoroughly modern.