--- title: "Stay It With Pride: The Ultimate South Eastern Ontario Pride Trail 2026" date: 2026-05-29T12:45:00-04:00 author: "South Eastern Ontario / Sud-Est de l'Ontario" canonical_url: "https://www.southeasternontario.ca/itineraries/stay-it-with-pride-the-ultimate-south-eastern-ontario-pride-trail-2026/" section: Itineraries --- ![](https://www.southeasternontario.ca/images/transforms/_maxWidth2400px/Blog-header-images-RTO-7.png) # Stay It With Pride: The Ultimate South Eastern Ontario Pride Trail 2026 South Eastern Ontario / Sud-Est de l'Ontario This time of year in South Eastern Ontario is all about waterfront patios, road trips, unforgettable nights out, and communities coming together to celebrate love in all its forms. From vibrant downtown parades to drag shows in barns, lakeside Pride parties, and small-town festivals bursting with heart, Pride season here is the perfect excuse to plan a rainbow-filled getaway. Whether you’re chasing every parade on the calendar or curating the perfect Pride weekend with your chosen family, here’s how to experience the very best of Pride across South Eastern Ontario in 2026. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/Blog-header-images-RTO-9.png?transformId=2340&site=default)**Stop #1: Gananoque & Napanee Pride Weekend (May 27–31, 2026)** Pride season kicks off early in South Eastern Ontario with an incredible opening weekend split between the waterfront charm of Gananoque and the community celebrations in Napanee. ***Gananoque Pride Festival*** The [Gananoque Pride Festival](https://ganpridealliance.ca/pride-2026/) returns May 27–31 with nearly a full week of events! Visitors can catch outdoor movie nights at the [1000 Islands Drive-In](https://www.1000islandsdrive-in.com/), live performances during the Royal Pride Variety Show, guided sunset kayaking tours on the St. Lawrence River, outdoor games, yoga sessions, youth programming, and late-night dance parties before the festivities culminate in the Pride Parade and Festival on May 31. The parade winds through downtown Gananoque before the celebration continues in Town Hall Park with vendors, entertainment, and waterfront festivities. While you’re in town, take advantage of Gananoque’s incredible walkability. Grab dinner overlooking the water, explore local shops along King Street, or book a cruise the 1000 Islands with [City Cruises Gananoque](https://www.cityexperiences.com/gananoque/city-cruises/) or [Rockport Boat Line](https://rockportcruises.com/) while you’re there. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/Blog-header-images-RTO-8.png?transformId=2351&site=default)***Napanee Pride Day*** Just under an hour west, [Greater Napanee Pride Day](https://greaternapaneepride.com/pride-day-2026) takes place May 30 with a Pride March beginning at Napanee Conservation Park followed by Pride in the Park festivities featuring live entertainment, vendors, and community programming. The evening wraps with the fan-favourite [Pride in the Country](https://www.instagram.com/p/DYKSd_oF8sp/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==) 19+ event at the Strathcona Paper Centre; a high-energy celebration packed with drag performances and dancing. For accommodations, Napanee makes an excellent overnight stop before continuing eastward through the region’s Pride celebrations. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/Blog-header-images-RTO-10.png?transformId=2354&site=default)**Stop #2: Kemptville, Brockville & Kingston Pride Week** The first two weeks of June are absolutely stacked with Pride events across the Rideau Canal and 1000 Islands corridor, making this the perfect multi-stop road trip week. ***Kemptville Pride (June 5–7, 2026)*** Hosted by[ North Grenville Pride](https://www.ngpride.ca/?utm_source=chatgpt.com), Kemptville’s celebrations blend small-town charm with energetic community events. The weekend begins June 5 with a Progress Pride flag raising ceremony and a nostalgic [90s-00s pre-Pride dance party](https://www.ngpride.ca/event-details/a-very-90s-00s-pre-pride-dance-party) before culminating in the North Grenville Pride Parade on June 7 followed by a massive after party at Kemptville Campus. Between festivities, grab coffee and breakfast at the proudly queer-owned [Bubba & Bugs Coffee Bar](https://www.facebook.com/bubbaandbugscoffee/), browse downtown boutiques, or spend some time paddling the Rideau waterways nearby. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/22-1000-ISLANDS-RIDEAU-WATERWAYS-FOOD-DRINK-BUBBA-BUGS26-1.jpg?transformId=2348&site=default)***Brockville Pride (June 5–6, 2026)*** Just down the highway, [Brockville Pride](https://www.facebook.com/brockvillepride/) packs a lot into one weekend. Festivities include a [Pride Prom](https://brockvilletourism.com/event/pride-prom-under-the-stars/), a [Girls, Gays & Theys Millennial Dance Party](https://brockvilletourism.com/event/brockvilles-girls-gays-theys-millennial-dance-party/), the annual Pride Parade along King Street, a vendor fair in Hardy Park, and an after-party drag show at the Barley Mow. While in Brockville, visitors can also explore the [Brockville Railway Tunnel](https://brockvilletourism.com/things-to-do/brockville-railway-tunnel/) — Canada’s first railway tunnel — or spend time enjoying the city’s beautiful waterfront parks and patios. Stay downtown to maximize walkability between Pride events, restaurants, bars, and attractions. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/Blog-header-images-RTO-11.png?transformId=2357&site=default)***Kingston Pride (June 6–14, 2026)*** [Kingston Pride](https://kingstonpride.ca/) remains one of the largest and most vibrant Pride celebrations in South Eastern Ontario, with more than a week of programming transforming the city into a rainbow-filled celebration. Highlights this year include: - [Rainbow Pride Roller Disco](https://www.eventbrite.com/e/rainbow-pride-roller-disco-tickets-1987630283684?aff=ebdssbdestsearch) - [Sapphic Delights Queer Pride Party](https://www.eventbrite.com/e/sapphic-delights-queer-pride-party-saturday-june-6th-tickets-1988932866745) - Two Spirit Celebration - [Drag in the Park](https://www.facebook.com/events/confederation-park/drag-in-the-park-june-2026/4218865555042990/) - Pride Community Fair - Kingston Pride Parade on Princess Street - [A sunset Pride Fundraising Cruise](https://www.eventbrite.ca/e/19-kingston-pride-fundraising-cruise-tickets-1988717262868) on Kingston’s waterfront - [Pride Recovery Brunch](https://www.rowenawhey.com/event-details/pride-recovery-brunch) to close out the festivities Kingston shines during Pride week thanks to its incredible combination of nightlife, restaurants, patios, waterfront experiences, and arts culture. Spend the day exploring downtown shops and cafés before heading into packed evenings of Pride programming. **Stop #3: Prince Edward County Pride Escape** For travellers looking for a slightly more curated, getaway-style Pride experience, Prince Edward County delivers one of the most unique weekends of the summer, including an immersive weekend-long Prince Edward County Escape hosted by [A Queer Camp](https://aqueercamp.ca/). The County’s Pride celebrations mix drag entertainment, winery experiences, dance parties, brunches, and beach-town energy across multiple communities. Highlights include: - The wildly popular [Oh Hayyyyy! Drag Show](https://www.eventbrite.ca/e/oh-hayyyyy-drag-show-tickets-1985418058860) at the Hayloft Dancehall - [Spice Queens](https://www.eventbrite.ca/e/spice-queens-drag-and-dance-party-extravaganza-tickets-1986768253328) drag and dance extravaganza - [Bitchin’ Bingo](https://www.rowenawhey.com/event-details/bitchin-bingo-at-karlo-estates-2026-06-19-18-00) at Karlo Estates Winery - Picton Pride Parade and Pride in the Park - [Pride After Dark at Base31](https://www.base31.ca/district/events/pride-after-dark) - [Drag Brunch at the Drake Devonshire](https://thedrake.ca/event/drag-brunch-w-miss-moco-2/) - Pride Party at Stock & Row Cidery This stop is ideal for travellers who want to blend Pride celebrations with wine touring, beach visits, boutique accommodations, and culinary experiences. Spend your mornings exploring wineries and sand dunes before heading into drag brunches, Pride parties, and dance floors late into the night. ![](https://www.southeasternontario.ca/images/transforms/_maxWidth1600px/Blog-header-images-RTO-12.png?transformId=2360&site=default)***Other Pride Celebrations Worth Adding to Your Summer*** **Tyendinaga Pride Car Parade - May 31, 2026** Tyendinaga Pride Car Parade kicks off Pride Month with its annual car parade departing from Centennial Park in Deseronto. **Cornwall Pride - July 18, 2026** Cornwall Pride Parade returns to Lamoureux Park with waterfront celebrations, community programming, entertainment, and family-friendly activities throughout the day. From waterfront parades and roller discos to drag brunches, vineyard dance parties, and community festivals, South Eastern Ontario’s Pride celebrations prove you don’t need a big city to find unforgettable experiences and welcoming spaces. So pack the rainbow fits, gather your travel crew, and hit the road: Pride season in South Eastern Ontario is calling. 🌈 READ ALSO - [ ![](https://www.southeasternontario.ca/images/transforms/_maxWidth250px/1000-ISLANDS-RIDEAU-WATERWAYS-RIDEAU-LAKES-ST-PAULS24-medium.jpg) Where to Stay Proud Places: A 2SLGBTQI+-Friendly Guide to Prince Edward County and Kingston ](https://www.southeasternontario.ca/articles/proud-places-a-2slgbtqi-friendly-guide-to-prince-edward-county-and-kingston/)