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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 (Updated May 30, 2024)

Paul Oswell

Paul Oswell is a British award-winning journalist and published travel author based in New Orleans, Louisiana in the United States. He frequently writes about luxury travel and bespoke experiences around the world. His books include Bucket List North America and The Great American Road Trip, as well as New Orleans' Historic Hotels. He has also been an editor of and contributor to several guidebooks/editions, including New Orleans, Florida, Orlando, Los Angeles, California and the United States. His work has appeared in Conde Nast Traveler, Travel & Leisure (both of which he has written multiple online travel guides for) and The Guardian, as well as dozens of international newspaper and magazine titles, and inflight magazines for major airlines.

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Pride Toronto’s 2024 Festival Weekend takes place from June 28th to June 30th and is one of the largest Pride celebrations in North America. The parade, which takes place on June 30th, 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.


Friday, June 28th

Morning

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.

Afternoon

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.

Evening

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 operates 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 several international pop sensations. You can turn up to cheer on the Trans Pride Rally and March, which also starts at 7 p.m. on the Community Stage, before scoping out the dance parties. Black Eagle, Toronto’s original leather and denim bar, is a safe bet for a lively time.


Saturday, June 29th

Morning

Revive yourself with brunch in the quirky pub-like atmosphere at Hair of the Dog. Aim for a seat on the lovely patio and enjoy chilaquiles or a fried chicken benny as you watch the revelers pass by.

At 2 p.m. on the main stage, get ready for one of the weekend’s highlights: the Drag Ball. Expect glitter-strewn fabulousness from drag queens and kings, as well as celebrity drag superstars.

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 to fuel up for the rest of the festivities.

Afternoon

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 Public School and is a wholesome showing of support for the queer community with face painting, storytelling, a magic show, puppet theater and more.

In the mood for more entertainment? The Wood Street Block Party runs from Friday through Sunday at Wood and Church Streets. A staple of Pride in Toronto, thousands take to the streets to dance and enjoy some of the best DJs in the city.

Evening

As you head into the night, you can keep the drag vibe going at Crews & Tangos, one of the city’s top drag bars offering nightly shows, two dance floors and karaoke.


Sunday, June 30th

Morning

It’s the biggest day of the weekend, so getting up early for a drag brunch is the perfect way to fuel up for the long day ahead. Try the cornflake-crusted French toast at Church St. 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.

Afternoon

If you’re exploring on foot, be sure to replenish your energy levels by packing a refillable water bottle and a few snacks. 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 Nathan Philips 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. More than 100 groups will march this year in support of this inclusive community.

Evening

You can spend the last evening of Pride Toronto by winding down in your cozy hotel or by enjoying 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, a lovely last dinner option is The Diner's Corner, an authentic, queer-owned West Indian spot with great saltfish and jerk salmon. Or you can head a couple of neighborhoods out to Parkdale and try one of the exotic concoctions at The Shameful Tiki Room.

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.

Where's your Pride?

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