At Heel Boy, we’re all about celebrating love, identity, and community year-round—but there’s something undeniably magical about Pride season. To keep the momentum going, we’re shining a spotlight on some of the amazing Pride events happening in our home cities of Kingston and Toronto. Whether you’re marching loud and proud, dancing ‘til sunset, or just soaking in the joy from the sidelines, there’s something for everyone—and these events are too good to miss.

🌈 Kingston Pride: Small City, Big Energy

Kingston is turning up the volume this Pride Month—and we’re here for it. From high-energy parades to waterfront drag shows and nostalgic throwback nights, the city’s Pride lineup is packed with celebration, creativity, and community spirit.

June 14 – Parade Day + All the Festivities

Start your day with the Community Fair at Confederation Park (10AM–5PM)—think local makers, live music, community booths, and good vibes all around. Then at 12pm, it's time to hit the streets! The Pride Parade kicks off at the Memorial Centre and makes its way down Princess Street to Ontario Street in a colourful, joy-filled march that welcomes all ages. Pro tip: this is your moment to break out the glitter, rainbow fits, and best footwear!!!

Bring the family to Rainbow Storytime (1–1:30PM) with KFPL, and cap off the evening with a free all-ages drag show (7–10PM) at the waterfront Visitor Information Centre. Hosted by the one and only Rowena Whey, the show features Perla from Canada’s Drag Race Season 5 alongside a dazzling lineup of local talent. Sunset + sequins = a perfect Kingston night.

June 15 – Recovery, but Make it Glam

Keep the celebration going with Rowena Whey’s Pride Recovery Brunch at The Wharf and Feather. You’ll get a delicious brunch and top-tier entertainment from Problemmathew and Tyffanie Morgan—a fabulous way to recharge while still soaking up the Pride atmosphere. Get your tickets here!

June 18 – 90s Drag + Costume Contest at The Grad Club
Channel your inner Spice Girl (or grunge king) for the “Now! That’s What I Call Drag” 90s Night. Hosted by Yuni Verse and supporting Trans Family Kingston, this 19+ event brings together iconic drag looks and a costume contest where your best 90s lewk could snag a prize. A throwback night for a cause? Yes, please.

June 19 – Movies in the Square

Round out the week with a free outdoor screening of Heightened Scrutiny, a powerful documentary about trans rights and legal activism, presented by ReelOut and Kingston Pride in Springer Market Square. A great way to reflect, connect, and continue the conversation.

🌈 Toronto: The Heart of Pride

Toronto doesn’t just celebrate Pride—it owns it. From iconic parades and city-wide parties to family-friendly events and immersive cultural moments, Pride Month here is a full-on experience. Whether you’re a longtime local or just visiting for the festivities, here’s what’s lighting up the city in June.

June 14 – Drag Storytime at the Zoo

Yes, you read that right—Toronto Zoo is serving storytime realness! From 2–3PM, little ones (and big kids at heart) can enjoy fun, inclusive storytelling hosted by fabulous drag performers under the Wildlife Marquee. It’s family-friendly, heartwarming, and 100% fabulous. Zoo admission gets you in!

June 19 – Pride Pool Party at Cabana Pool Bar

Pack your best poolside lewk and head to Cabana for one of the splashiest Pride events in the city. Running from 6–11PM, this lakeside bash features RuPaul’s Drag Race star Lexi Love, DJs, dancing, and serious summer vibes. Sunscreen + sequins highly recommended.

June 20 – Night at the Aqueerium

Get ready to dance under the sea! Ripley’s Aquarium transforms into a Pride-themed party zone from 8PM–12AM with DJs, drag, and drinks among the jellyfish. It’s a surreal (and totally Instagrammable) experience unlike anything else in the city.

June 26–29 – Pride Festival Weekend + Parade Day

This is the heart of Pride Toronto. For four unforgettable days, the Church-Wellesley Village comes alive with music, drag, art, and community—culminating in the legendary Pride Parade on Sunday, June 29. The parade kicks off at 2 p.m., starting at Bloor Street East and Church Street, and winds its way down to Nathan Phillips Square. Expect packed stages, incredible performances, and powerful moments of connection all weekend long. Whether you're marching or cheering from the sidelines, it's a celebration you won't want to miss.

💫 Brand Spotlight: Intentionally Blank

One of our favourite brands on the shelves—Intentionally Blank—isn’t just about great shoes (though trust us, the shoes are really great). It’s a queer-owned, human-forward lifestyle brand that’s all about helping you express your style without limits.

We love how their designs strike the perfect balance between playful and minimal, statement-making and wearable. Whether it’s a bold sandal or a sleek everyday heel, every pair is made with intention (pun fully intended). It’s fashion that doesn’t follow rules, and we’re proud to carry a brand that celebrates identity, expression, and individuality—every step of the way.