Middletown PrideFest 2025: pride march, festival & concert

In the heart of the Connecticut River Valley, Middletown PrideFEST returns on Saturday, June 7, 2025. Don’t let the city’s modest size fool you – Middletown Pride has exploded into Connecticut’s largest Pride Month event, drawing 30,000+ people in 2024 and aiming even higher in 2025. Organized by the City, local LGBTQ Commission, and a coalition of community groups, Middletown PrideFEST is a full-day extravaganza (12 PM – 10 PM) blending a parade, rally, concerts, drag shows, and street fair into one joyous celebration. All are welcome as Middletown proclaims loudly that this inclusive city “has Pride!”

What Happens at a Middletown PrideFEST?

Pride March

Festivities kick off at noon sharp with a Pride March down Main Street. More than just a parade, this is styled as a march for visibility and justice. The route starts at the north end of Main St. (near St. John’s Square) and promenades through downtown, ending near the South Green. Local organizations, schools, companies, and churches will proudly march for equality. Many carry banners declaring support. Floats are fewer than a big-city parade, as Middletown emphasizes marching groups to keep it grassroots.

Each year has a focus; 2025’s emphasis is on at-risk transgender services and protections, given the political climate.

Expect the sidelines to be packed. Families with kids on shoulders, college students (Wesleyan University is here), and folks from across CT all gather to celebrate Pride. Last year, spectators topped 30k, basically doubling Middletown’s population downtown.

The march lasts about 1 to 1.5 hours. It’s more informal than a choreographed parade, participants chant, wave, and even break into dance! Keep an eye out for spontaneous Cupid Shuffle or Electric Slide moments in the street!

Pride Rally

After the march, people convene on the South Green Stage (a big outdoor stage on the city’s South Green). City officials and Pride organizers host the rally, which features speeches by activists and officials highlighting accomplishments and ongoing struggles of the LGBTQ+ community. Given the focus on trans issues in 2025, expect a trans youth speaker and representatives from orgs like CT TransAdvocacy.

The rally blends seriousness with celebration. You might hear spoken word poetry, a short drag performance, or choir singing “True Colors” between speeches.

Festival & Concert

Now the party truly ignites! Main Street is closed off and transforms into an open-air PrideFest. Starting late afternoon, a Showcase Concert on the South Green stage rocks the city till night. The lineup is diverse: local bands, maybe a Broadway singer (CT has a vibrant theater scene), and definitely drag performances that dazzle.

By early evening, headliners come on. Prior PrideFESTs featured acts like Christine O’Leary (comedian) and RuPaul’s Drag Race alums. 2025 specifics not yet announced, but expect big energy.

All along Main St. (which is linear and perfect for a street fest) you’ll find vendor booths and info tables. Over 100 vendors come, from local artisans and LGBTQ+ organizations to corporate sponsors and tons of food trucks. Try everything from fried dough to tacos to Connecticut’s famous pizza sold by a local spot. There’s likely a beer garden area by Eli Cannon’s (a pub) for 21+.

Pride for the Whole Family

Middletown Pride is proudly family-friendly. There’s usually a Kids Corner with face painting, balloon animals, maybe a bounce house. The 2025 edition might feature a Drag Queen Story Hour or craft tent for kids.

They also often have a Youth and Teen Zone with things like open-mic karaoke or dance-offs for the younger crowd.