The origins of Bloor-Yorkville are firmly rooted in live music. In the 1960s, Bloor-Yorkville was a cultural epicenter for some of Canada’s greatest musical talents, including Joni Mitchell, Neil Young, and Gordon Lightfoot, as well as literary greats Margaret Atwood and Dennis Lee. At that time, our neighbourhood was Canada’s capital of the hippie movement, with the youth of the day frequenting local coffee shops to hang out with and be inspired by the creative talents frequenting the area.
Today, Bloor-Yorkville is home to the TD Toronto Jazz Festival as well as our Summer Music in the Park programming – two events that keep our history with music alive. Additionally, a few of our fantastic bars and restaurants have live music nights where you can enjoy everything from jazz to soul and funk.
Best Live Music in Toronto
The Pilot has a longstanding history with live music. A Bloor-Yorkville staple since 1944, The Pilot hosts Saturday matinee jazz performances! Taking place on the Pilot’s ground floor every Saturday from 3 pm – 5 pm, guests can enjoy live jazz with a small cover charge of $10. Seating is on a first-come, first-served basis, so we suggest stopping by earlier for brunch (reservations are accepted both inside and on the Flight Deck Rooftop,) and then heading downstairs to enjoy the show. Next up is the Karl Silveira Quartet on September 3rd. You can find the entire schedule online here.
22 Cumberland Street
It makes sense that the Italian fine-dining restaurant, Sofia, would add live music to its mix! The restaurant already merges food and art, featuring one-of-a-kind pieces from Taglilatella Galleries, located next door. Guests can dine next to everything from an original Banksy or Andy Warhol piece, and soon alongside Toronto’s top jazz, funk, and soul bands as well. While their new music schedule hasn’t been released, you can take a look at the upcoming bands here. Be sure to keep an eye out for updates!
99 Yorkville Avenue
Founded by Andrew Carter of The Oxley, Middle 8 was designed to be a live music venue as an “ode to Yorkville’s past as a music capital.” While there’s also a large back patio, the music happens downstairs in the cozy bar area, which has a distinct speakeasy feel. Performances take place Thursday through Saturday from 9 pm-midnight, so it’s a great post-dinner destination. There’s an extensive cocktail and wine list, as well as shareable plates for those who are feeling a little snacky.
119 Yorkville Avenue
While not a restaurant or bar, the Heliconian Club is a unique venue in itself. Originally built in 1876, the Heliconian Hall is an example of Carpenter’s Gothic Revival architecture and is one of only a few examples of this style within Southern Ontario. The structure is deemed a National Historic Site and features a simple board and batten exterior, a Victorian rose window, and carved rafters in the vast vaulted ceiling. Their club hosts a Saturday afternoon Concert Series, which is a curated selection of performances selected by members of the club. Tickets are available for non-members and can be purchased online here.
35 Hazelton Avenue
PS. If you’re interested in discovering more unique architecture in the area, be sure to check out our guide to a Historic Walking Tour.