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The Perfect Getaway: A weekend in Toronto for Pride

Headed to Canada to take part in the Pride Parade? Follow along on our fun-filled itinerary to create the perfect stay in Toronto. | By Paul Oswell | May 27, 2022

Pride Toronto’s 2022 Festival weekend takes place from June 24th to 26th and is one of the largest Pride celebrations in North America. The parade has a decades-long history and was borne out of mass protests following aggressive police raids in the early 1980s. It’s now a huge, colorful and inclusive celebration of local LGBTQ culture, with myriad parties and parades happening in and around the city. Here’s how to create a perfect getaway if you’re planning to visit over this incredibly fun weekend:

  • Take Pride: Where and how to enjoy the main events of Pride Toronto 2022

  • Fuel up: Support queer-run and LGBTQ-focused places to eat and drink

  • Clue in: Discover the history of the city’s queer community and see its cultural touchstones

Friday, June 24th


Arrive in Toronto and check into Hilton Toronto or the DoubleTree by Hilton Hotel Toronto Downtown. Both properties enjoy plum locations in the city and are close to the Pride Toronto Parade route and lots of the local LGBTQ+ nightlife.

You should spend your first morning exploring Church-Wellesley Village, a neighborhood that the city’s LGBTQ+ community have made their own. You can hop onto the subway right outside Hilton Toronto at Osgoode Station and take Line 1 straight to the Wellesley stop. DoubleTree by Hilton Hotel Toronto Downtown is even closer and is walkable in 20 minutes, or just two stops on the subway from the adjacent Dundas Station.


A natural hub is the wonderful Glad Day Bookshop, which has the distinction of being the world’s oldest operational queer-focused bookstore.

Glad Day Bookshop

A beloved institution for more than 50 years, Glad Day Bookshop is a safe space for activism and a friendly spot for socializing. It even hosts one of the most fabulous drag brunches in town, as well as some surprisingly feisty nighttime parties. The community bulletin board is a goldmine of information, and there’ll be lots of flyers and posters for events happening across Pride Toronto weekend.

If you need to finesse your look for the weekend, then drop into Grapefruit, a clothing and decor concept store that also uses its voice to support the LGBTQ community by creating a warm, welcoming environment for all. Out on the Street is another queer-focused clothing store that is a firm village favorite.


You’ll need some sustenance to fuel your weekend’s activities, and a great starting place is the legendary Woody’s, which has been open since 1989 and is among the city’s best-loved queer bars. It’s likely to be crowded, but Woody’s also operate a sister bar, Sailor, that is right next door. Expect saucy competitions and lively DJ sets all weekend. For dinner, queer-friendly Kinka Izakaya is a casual Japanese restaurant with a wonderful selection of shareable sushi plates and noodle dishes.

At 7 p.m., the opening ceremonies take place on the main stage with the first of the Festival Weekend’s acts, including Grace Hamilton, AKA Spice, also known as ‘The Queen of Dancehall.’ You can turn up to cheer on the Trans March, which starts at 8 p.m. on the corner of Church and Hayden streets, before scoping out the dance parties. The Black Eagle, Toronto’s original leather and denim bar, also on Church Street, is a safe bet for a lively time.

Saturday, June 25th


Revive yourself with breakfast or brunch at Smith on Church Street, an elegant, queer-owned spot. Aim for a seat on its lovely patio and enjoy brisket hash and lemon curd doughnuts as you watch the revelers pass by. Afterward, you should have time to cheer on the runners of the Pride and Remembrance Run, which raises money every year for LGBTQ charities.

Pride Toronto is in full flow by this time, and a couple of fun daytime events are worth your attention. Family Pride runs all day at Church Street Junior Public School and is a wholesome showing of support for the queer community.


At 1 p.m. on the main stage, one of the weekend’s highlights, the Drag Ball, takes place. Expect glitter-strewn fabulousness from drag queens and kings, with surprise guests from “Drag Race Canada.”

Duck out of the crowds and walk or take a cab a few blocks from the village to enjoy a quick lunch from the plant-based Mexican menu at queer-run restaurant La Bartola, or grab a juice from Anti Vice Juicery before lining up to cheer on the Dyke Rally & Dyke March.

Lavender Menace

There’s bound to be some femme-forward hedonism at Lavender Menace, a lesbian-owned bar that combines Southern comfort food (cheddar grit cakes, anyone?) with delicious, whimsically named cocktails such as the gin and rose-flavored signature drink, “Votes For Women!”

In the mood for more entertainment? The Green Space Festival runs from Thursday through Sunday at Barbara Hall Park. Every day is a different theme and they line up the city’s best musicians, DJs and drag performers, all in a buzzing alfresco space.


As you head into the night, you can keep the drag vibe going at Nightowl, a dynamic music venue that also serves up tasty charcuterie boards with vegetarian options or look for parties with lively music offerings courtesy of top Toronto DJs.

Sunday, June 26th


It’s the biggest day of the weekend, so try and get up early for a drag brunch, to fuel up for the long day ahead. Try the cod fish croquettes at Church Street Garage, where The Imperial Court of Toronto holds its regally campy proceedings.

You can also take some quiet time to learn about the city’s queer community. A self-guided tour using apps such as Queerstory will lead you around the cultural and historical spots that tell the story of LGBTQ folk in Toronto. You can even access mini-documentaries and archival footage through the app as you walk.


It might be a long afternoon, so don’t forget to pack a refillable water bottle and plenty of sunscreen. If you’ve been exploring on foot, it’s a good idea to replenish your energy levels. For some on-the-go deliciousness, try the grilled chicken or lemongrass tofu sandwiches from Banh Mi Boys. If everywhere is jam packed, a few blocks outside of the Gay Village are places such as Sin & Redemption, which serves casual pub food, and you can even try poutine —French fries topped with cheese curds and gravy — considered a Canadian delicacy.

The focus of the whole weekend, the main Pride Parade processes at 2 p.m. from the corner of Church and Bloor streets all the way down Yonge Street before ending at Yonge-Dundas Square.

Pride parade

The sheer diversity of the city’s LGBTQ community is on display here, with stunning costumes, sound systems and special celebrity guests all joyfully saluting the best of the city’s queer culture. This year’s International Grand Marshall is Lady Phyll, a celebrated British activist and public speaker, and Pride Toronto’s chosen charity this year is the Black Coalition for AIDS Prevention, which works to educate and respond to the threat of HIV and AIDS in the city’s Black, African and Caribbean communities.


The last evening of Pride Toronto can be either a winding down or one last night of partying. There will be plenty of last hurrahs taking place at bars around the village — try the patio at Boutique Bar or the dance floors at Crews & Tangos.

If you feel like taking things down a notch, though, then head a couple of neighborhoods out to Parkdale and try one of the exotic concoctions at The Shameful Tiki Room. More locally, a lovely last dinner option is The Diner’s Corner, an authentic, queer-owned West Indian spot with great saltfish and jerk salmon.

Whatever your tastes or interests, you’ll find Pride Toronto’s Festival Weekend an inclusive and inspiring time, where diversity and self-expression are celebrated with colorful gusto, and the city itself provides an ideal backdrop.

Paul Oswell is an award-winning travel writer, and has been reporting from all seven continents for over twenty years. He is based in New Orleans and is the author of “The Bucket List North America: 1,000 Adventures Big and Small.”

Where's your Pride?

Catch some of the nation's biggest Pride festivities with this calendar of activities.

Find a Pride Weekend Near YouView Hilton's Pride Landing Page