The Pilot is Yorkville's tavern, open since 1944 and still going. Multi-level, aviation-themed, with several bars, a private event floor and a big rooftop patio. Top 40 most nights, jazz on Saturdays. Here's the honest rundown before you head over.
The sceneWhat it's actually like
The Pilot is one of Toronto's oldest bars and it wears that history well. It opened in Yorkville in 1944 and has been a favourite for locals and visitors ever since. The vibe is relaxed and friendly, the kind of room you come to for a drink, a meal and good company rather than a velvet rope. Vintage aviation memorabilia covers the walls, which gives the whole place a nostalgic, lived-in feel you don't get from a new build.
It's a versatile spot. Ground floor has the lively bar and cozy seating, the second floor is a private event space, and up top there's a large open-air rooftop patio with great views. There are bars on both the ground floor and the patio, so you're never far from a drink. This isn't a bottle-service club, it's a proper tavern that's kept its charm while quietly keeping up with the times.
Quick factsKnow before you go
The Pilot's floors & the jazz matinees
Three levels, each with its own feel. The ground-floor bar, the second-floor private event space, and the rooftop patio up top. The standout is the Saturday afternoon jazz.
Reserve
Reserve a table at The Pilot or walk in
The Pilot takes reservations online and by phone, and they hold space for walk-ins too, so you can just show up. For a group of 10 or more, email the bar ahead to line it up. Drop your details below and we'll pass your request along. Heads up: the bar gets busy after 9pm, and the Saturday jazz matinees are first-come, first-served, so come early for a seat.
Real talk: The Pilot isn't one of our partner rooms, so this isn't the club's official guestlist. We're independent. Leave your info and we'll text you back with the best play for the night, including rooms where we can get you in for real.
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The Pilot Toronto: the full review
Address & location
The Pilot is in Yorkville at 22 Cumberland St (M4W 1J5), right near Yonge and Bloor. Easy to reach by TTC or car, central enough that it's a good place to meet friends before or after anything else downtown.
The room
It's a large, multi-floor bar with plenty of space. Casual, lively and welcoming, with that vintage aviation theme running through the decor. Ground floor for the bar and seating, a private event space on the second floor, and a big rooftop patio up top. Wherever you land, it's comfortable.
Who's there
A real mix. Locals, longtime regulars, after-work groups, and Yorkville visitors. It's not a scene or a dress-to-impress crowd, it's people who come for the room, the drafts and the history. That's the whole appeal.
What's great
- The beer. Over 17 different drafts on tap, so there's always something new to try.
- The patio. A large rooftop patio with good views, plus multiple bars and dining areas across the floors.
- The history. Open since 1944 with the aviation decor to match. It's a piece of Toronto, not a template.
What to know going in
- It gets busy after 9pm. Longer waits and a crowded room once it fills up.
- Jazz seating is first-come. The Saturday jazz matinees fill fast, so arrive early for a good seat.
Move like you know
- Coming for the Saturday jazz matinees? Get there early, it's first-come, first-served, and there's a $10 cover at the door.
- Check the event schedule ahead so you can plan around trivia nights, live music and whatever else is on.
- Got a group of 10 or more? Email the bar in advance to sort your visit.
The music
Music at The Pilot shifts with the event and the time of day. You'll hear a mix of Top 40 and jazz, and the bar hosts live music too, the Saturday jazz matinees being the signature. Whatever you're into, there's usually something playing that fits.
What to wear
Dress code is casual. Come comfortable. That relaxed, no-fuss approach is a big part of why the room feels as welcoming as it does, so don't overthink it.
Cover charge
The Pilot usually has no cover, though some events charge at the door depending on what's on. The Saturday jazz matinees run a $10 cover with seating first-come, first-served, so get there early if jazz is the plan.
Age limit
It's 19 and over. Ontario drinking age, so bring real ID. Keeps the room grown and easy.
Reservations, walk-ins & bottle service
The Pilot takes reservations online and by phone, and they hold space for walk-ins, so you can show up without one. For groups of 10 or more, email the bar ahead to arrange it. There's no booth or bottle service here, that's not what The Pilot is, it's a casual tavern built around good drinks, food and the room itself. Drinks run mid-range: mixed drinks $13 to $55, plus the 17+ drafts.
