Explore Toronto’s largest 2SLGBTQ+ neighbourhood with these local-approved picks.

A lot can happen in Church-Wellesley Village on the weekend—and it doesn’t need to be Toronto Pride Month (though that’s not a bad time to visit!). 

Here’s an itinerary of our favourite go-tos in the Village, so you can experience the best of the neighbourhood and maybe discover something new. 

Friday night at Woody’s

Opened in 1989, Woody’s (467 Church St.) has been a major focal point of Village life for decades. And together with its brother bar Sailor (next door), Woody’s has been described as Toronto’s friendliest and most welcoming gay bar—so what better place to introduce yourself to the Village? Cheer on (or try your luck in?) the best chest and best butt contests, Thursday through Saturday—it’s a long-standing local tradition. 

Saturday: Books, Buddies and Black Eagle

Browse Glad Day Bookshop (499 Church St.). Established in 1970, it has a strong claim to being not only Canada’s first queer-focused bookstore, but also the oldest one anywhere. More recently it has added an event space and café with an eclectic menu that changes from time to time but tends toward the hearty (say, vegan bourbon chili, fish stew, biscuits, lasagne). 

For the evening, book a show at Buddies in Bad Times Theatre (12 Alexander St.). Established in 1979, Buddies bills itself as “Toronto’s leading destination for artistically rigorous alternative theatre,” and has been a seminal proving ground for queer playwrights and performers. After the applause, Buddies turns into a nightclub on the weekend, with drag queens taking centre stage. 

After your culture fix, you can either head to Crews & Tangos (508 Church St.) for lively drag performances and upbeat music or Black Eagle (457 Church St.), Toronto’s original (leather and denim) cruising bar. Depending on the night, you could stumble upon a party like Freak Like Me, which sees the Eagle turn out some of the best sounds in the city, welcoming Toronto DJ vanguards like Chippy Nonstop, Karim Olen Ash, and Babygirl. X-rated movies play on the many screens inside the venue, which are turned into gaming stations on Tuesdays for Gaystation night. 

Sunday: Drag Brunch and a Rooftop Barbecue 

If you’re in the mood for a drag brunch to start your Sunday, check out our guide to Toronto drag for options.  

After a day of walking around the neighbourhood and stopping for patio drinks, if the weather’s nice, head back to Black Eagle for its famous Sunday barbecue. From mid-afternoon to 9 p.m., the party takes place at an upstairs patio showcasing the mural artwork of Toronto artist Jay Dampf. Or, if you feel the night is young, loop back to Woody’s for the Smoking Hot Divas show, starting at 11 p.m.

Getting to Church-Wellesley Village

  • Take TTC subway Line 1 Yonge-University to Wellesley Station, then walk east to Church Street
  • Or take the 94 Wellesley bus to Church Street