Pride Toronto’s 2023 Festival weekend takes place from June 23rd to June 25th and is one of the largest Pride celebrations in North America. The parade, which takes place on June 25th, 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 23rd

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.

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 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 pop sensation Rêve, Saucy Santana, PriXm, Pogi and more. You can turn up to cheer on the Trans Pride Rally and March, which starts at 7 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 24th

Morning

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.

At 11 a.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 and special guests, including Sasha Colby, Anetra, Jimbo, Pythia, Miss Fiercalicous, Kimmy Couture and more.

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.

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 Junior 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 Thursday 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 25th

Morning

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.

Afternoon

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 Nathan Philips Square.

Evening

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 a British award-winning journalist and published travel author based in New Orleans, Louisiana in the United States. 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 guide books/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.