The Perfect Getaway: A weekend in Toronto for Pride

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, which has the distinction of being the world’s oldest operational queer-focused bookstore. 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 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 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 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.

At 6 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 Afterparty, which starts at 7 p.m. on the Community Stage, before scoping out the other dance parties. Black Eagle, Toronto’s original leather and denim bar, is a safe bet for a lively time.

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 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, a magic show, puppet theater, 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.

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 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.