The Perfect Getaway: A weekend in Toronto for Pride
Headed to Canada to take part in the Pride Toronto? Follow along on our fun-filled itinerary to create the perfect stay.
By Paul Oswell | May 27, 2022 (Updated May 14, 2026)
Pride Toronto’s 2026 Festival Weekend is one of the largest Pride celebrations in North America. The parade, which takes place at the end of June, has a decades-long history and was borne out of mass protests following 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.
Day 1
Morning
Arrive in Toronto and check in to Hilton Toronto or DoubleTree by Hilton Hotel Toronto Downtown. Both hotels enjoy plum locations in the city and are close to the Pride Toronto Parade route and lots of the local LGBTQ+ nightlife. 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 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 a drag brunch, as well as some nighttime parties. The community bulletin board is a goldmine of information, and there’ll be flyers and posters for events happening across Pride Toronto weekend. If you need to finesse your look for the weekend, then drop into Out on the Street, a clothing store that is a firm village favorite.
Evening
You’ll need some sustenance to fuel your weekend activities, and a great starting place is Frenchy Bar et Brasserie at Hilton Toronto. The contemporary, Parisian-inspired lobby bar and lounge offers French classics with an innovative twist. Also consider Toronto’s 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, which is 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.
Day 2
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. During festival weekend (June 25-28, 2026), 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 take a cab a few minutes away from the village to enjoy a quick lunch from queer-run restaurant O'Grady's on Church or grab a juice from Anti Vice Juicery 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, stage and roaming performance art, and more. In the mood for more entertainment? The StreetFair runs from Friday through Sunday, spanning several blocks on Church Street from Bloor Street to Dundas Street. Peruse over 200 stalls of unique shops, tasty eats, hands-on activities, and more.
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.
Day 3
Morning
For the final day of festival weekend, 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 kicks off at 2 p.m. from the corner of Rosedale Valley Road and Park Road before making its way down Yonge Street and ending at Nathan Philips Square.
Evening
Spend the last evening of Pride Toronto winding down in your cozy hotel or 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.
Planning tips
Take advantage of your hotel’s on-site dining offerings and, if you’ll be out and about, reserve any off-site meals ahead of time because popular brunch and dinner spots fill up fast during Pride.
Plan extra time to get to events due to road closures and packed transit, even if you’re staying close to the events, especially for the Trans March (Friday), Dyke March (Saturday), and the main Pride Parade (Sunday).
Leverage on-site hotel amenities that can make your Pride weekend smoother: pools for mid‑day cooldowns, fitness centers for a quick reset, and room service when you need a break from the crowds.
Toronto weather in June can shift from hot sun to sudden showers. Bring sunscreen, a light layer, and something fun and colorful for the parade route.
Paul Oswell
Paul Oswell is a British award-winning journalist and published travel author based in New Orleans, Louisiana. 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 published by Dorling Kindersley (owned by Penguin), 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.
Explore more places that go all out for Pride
The best cities to celebrate Pride in the US
Celebrate Pride this year at some of the best cities around the United States. Discover New York, Philadelphia, San Francisco and more.
My 9 Things: What I Packed for Dallas Pride
Discover Hilton's social media community manager Dannii Ceniceros nine essential items for the perfect Dallas Pride weekend. Learn what to bring today.
Best places to stay in Washington, D.C. for WorldPride
Celebrate WorldPride in Washington, DC with vibrant events and local attractions. Discover the best activities, things to do, and where to stay.
New York City nightlife: What to do when the sun goes down
Discover the best things to in New York City at night. Explore unique experiences including jazz clubs, Broadway shows, and more. Plan your getaway today.
Read more:
Find travel inspiration