Brunch is a serious topic in Toronto, so when a new menu hits the city it’s not to be taken lightly! Launching a few weeks ago, in time for Sunday mornings on the sun-filled rooftop, The Pilot introduced their version of the city’s most revered weekend meal: Sunday brunch. The Pilot, known as a bit of an institution in the Bloor-Yorkville area, celebrates its 75th birthday later this year, so as we approach this milestone we thought a brief history was in order. The Bloor-Yorkville area is rich in history with its beginnings as an enclave for the 1960’s music icons and while much has changed since then, what remains is the mix of old and new, leading to the historic charm and modern design of the area. Recently, we chatted with Al Stuart, managing partner of The Pilot, to catch us up on decades past and what has led The Pilot to where it is now.
The Beginning: 1944
Opening in 1944 during World War 2, the restaurant was named in honour of the pilots serving during this time. As legend has it, there was a pilot training base in Toronto and this was a way for the owners to provide a go-to establishment for those in training. Over the years, the name changed a couple of times, a liquor license was acquired, the location switched from 800 Yonge St to 22 Cumberland (in 1972), and a second floor (The Stealth Lounge) and rooftop (The Flight Deck) were added. Yet throughout these changes, what’s remained the same is the feel-good atmosphere welcoming to every age and every walk of life.
The High-School Hockey Friends Takeover: 1987
After visiting the Pilot at 15 years old for the first time, Al and his friends, who grew up around the corner and attended Jarvis Collegiate (the oldest school in Toronto!), often joked that one day they’d own the restaurant. Ten years later they did, and many of the original group of friends are still in on the business together. Pieces of entertaining history remain within the walls, such as the rumour that the original bar was physically carried over to the new location by a few of the regulars. There are also accounts of TIFF stars sneaking in incognito and a wildly amusing tale of Colin Farrell attempting to perform an Irish jig on the tables.
Then & Now:
As Bloor-Yorkville has evolved, so have the efforts of The Pilot. In the early 2000s, there were significantly fewer residents in the area, meaning weekends in the restaurant were fairly empty. These days, The Pilot proves to be a peaceful escape on Saturday and Sunday, removed from the fast-pace of the weekday hustle and bustle while remaining favorably located in Bloor-Yorkville. This was the impetus to introduce Sunday Brunch, a beloved ritual of many Torontonians. The rooftop, which is open seasonally, is the perfect backdrop to a casual Sunday morning. The brunch menu brings in all the essentials from avocado toast, to eggs bennies and Shakshuka. Of course, the other essentials are there as well, in for the form of mimosas with fresh-squeezed juice, French 75’s, or a classic Canadian choice: a Bloody Caesar.
“I love the mix of people who come here … we’re in a really great spot in Bloor-Yorkville which brings in so many types of people. We really saw that during the Raptors playoffs. We see people of all walks of life and backgrounds”
It’s safe to say the team at The Pilot is passionate about its team members (many of whom have been there for 10, 15, and 25 years), the community of Bloor-Yorkville, and its clients. Maintaining its authenticity is important for Al and the team, but so is finding ways to continue to grow with our neighbourhood. After nearly 75 years, The Pilot has managed to keep its charm, its laid-back atmosphere, and its dependability as a go-to community hub, so we’re sure the team will continue its legacy!
You can check out the new brunch menu below, make an online reservation here, or stop by and visit at 22 Cumberland Street. The Pilot also hosts Saturday afternoon jazz (and has for 32 years!).