Sneak away to Toronto for a much-deserved romantic retreat, squad getaway or friendcation. Here’s how to explore Canada’s largest 2SLGBTQ+ neighbourhood.

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

Here’s a curated itinerary of our favourite go-tos in the gaybourhood. 

Day 1

Shop the Church Street strip

Get started by checking out Church Street’s retail scene. Browsing the shelves of Glad Day Bookshop is a must. Established in 1970, Glad Day is the oldest queer-focused bookstore in the world. Other shops to stop for include: Out On The Street for sex-positive gear and clothing, and Dead Dog Records for classic vinyl and CDs.

Indulge in dinner and drinks

Sit down to margaritas and Mexican food at Casa Mezcal, known for its laid-back rooftop patio vibes. But you can’t go wrong with drag shows and pizza at The Drink!

Explore the local theatre scene

Next, catch a show at Buddies in Bad Times Theatre. 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. 

It’s a great spot for cabaret, comedy and music, too. 

Dance into the night

On weekends, Buddies turns into a nightclub after the final curtain call, with drag queens taking centre stage. Want to extend your night? Head to Crews & Tangos for lively drag performances and upbeat music or Black Eagle if you want to try your luck at Toronto’s original leather and denim cruising bar. 

Day 2

Go brunching

In the mood to start Sunday with queens in sequins? Check out our guide to Toronto drag for local drag brunch options. 

But if you’re looking for something quieter so you can reconnect with your SO or debrief with your pals, Cherie Bistro serves up the classics and more in a welcoming low-key environment.

Get in your steps at Allan Gardens

Work off those créme brûlée pancakes by strolling over to historic Allan Gardens and its famed Conservatory. The indoor botanical garden consists of five Victorian-era greenhouses boasting glorious orchids, bromeliads, cacti and koi fish. 

If you brought your fur baby with you to Toronto, take advantage of the public park’s off-leash dog park.

Treat yourself to a massage

Elmspa is a boutique day spa in the heart of The Village much loved for its massage, body care and facial services. 

The nearby Gesund clinic also offers treatments by Registered Massage Therapists. Gesund shares space with Apothecary, where you’ll find an astonishing array of Canadian-made natural skincare. 

Pro tip: book body treatments in advance to avoid disappointment.

Also see: Toronto Hotels with Next-Level Spas

Enjoy a Sunday feast

Cap your Toronto visit with one final meal in The Village. Black Eagle’s Sunday rooftop patio BBQ is the hottest in the city, running weekly from 3 to 9 p.m., and there is a retro dance party afterward. 

And of course, sushi is always apropos: try mainstay Kawa Sushi, aburi experts Torch Sushi or the tavern-style Kintaro Izakaya