Annapolis Pride Returns October 3 with Ryan Cassata Headlining
The family-friendly celebration brings its own brand of acceptance and accessibility to suburban Maryland each year.
“We always say that our Pride, in comparison to other Pride celebrations around us, is definitely more family-friendly, and we are always very mindful of accessibility,” says Jake Trudeau, chair of Annapolis Pride. “It’s just reflective of the area, and fits with what the surrounding community wants from us, too.”
Beyond its family-friendly, accessible Pride celebration, Trudeau says Annapolis has warmly embraced the LGBTQ community. The city earned a perfect score of 100 on the Human Rights Campaign’s Municipal Equality Index, which measures LGBTQ inclusion in municipal laws and policies.
“Our first parade and festival was in 2019 under former Mayor Gavin Buckley,” Trudeau says. “I think he really set the stage and the tone for the acceptance by the city. And we were able to work with the folks at the city and county level, including Buckley and [Anne Arundel] County Executive Steuart Pittman, who have been incredible champions for the community.
“They’ve been joined by Congresswoman Sarah Elfreth and State Delegates Dana Jones and Dylan Behler, so we’ve had great representation from a political standpoint, as well as a supportive community that embraced and uplifted us, and helped make us successful,” he adds.
This year’s Pride takes place on Saturday, October 3, with the parade kicking off at 11 a.m. at Calvert and Bladen Streets. The route follows Northwest Street to Church Circle, then continues down West Street before turning left onto Amos Garrett Boulevard and right onto Constitution Avenue, ending at Maryland Hall.
Annapolis Pride has designated a roped-off viewing area at The Graduate Hotel for people with disabilities or accessibility needs. The parade takes place rain or shine.
The festival runs from noon to 6 p.m. at Bates Athletic Complex on Spa Road. Admission is free. Parking at Navy-Marine Corps Memorial Stadium costs $24 in advance or $30 on the day of the festival.
The festival will feature more than 150 vendors — from community organizations to local businesses — offering swag and information, and a variety of food trucks catering to all tastes, with vegan and vegetarian options available.
A “Kids Zone” will offer arts and crafts, face-painting, and bounce houses. A new “sensory tent” will offer a space away from the stages for anyone feeling overwhelmed or overstimulated. Equipped with fidgets, coloring activities, and tactile elements like sand and putty, the tent will give attendees a place to relax and recalibrate before returning to the festival.
Musicians and entertainers, many from the area, will perform on two stages: the Main Stage, running from noon to 6 p.m., and the Songbird Stage, running from 1-5 p.m. ASL interpreters will be available at the Main Stage for deaf and hard-of-hearing attendees.
Singer-songwriter and transgender activist Ryan Cassata, whose music spans folk punk, blues, and pop punk, will headline the festival and serve as the parade’s grand marshal. He will perform with D.I.Y. Guy, an all-trans guy band, on the Main Stage at 5 p.m.
“We’re really excited about having Ryan perform this year, especially given the political environment,” Trudeau says. “Our theme this year is ‘United in Pride, Together We Thrive.’ I think it’s important, more now than ever, to stand together.”
A “Pride After Party” runs from 6-11 p.m. at The Graduate Hotel, 126 West Street, with headliner DJ Dave O performing from 6:30-8:30 p.m. Shuttles will be available from the festival grounds to the hotel.
“I grew up in a very sheltered, more closed-minded space,” Trudeau says. “Being a part of this event and this community has been life-changing for me. There’s always part of the celebration where I get emotional, because my motto is ‘Be who you needed when you were younger.’ And I think about how my life could have been different if I had seen this [community] support when I was a child. Hopefully, there’s someone out there that I can help by being visible, by being out.”
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