• Courtesy
• Seton McIlroy and Gabe DeLeon

Vermont's first Pride celebration took place in Burlington in June 1983. Participants faced public vitriol and marched, risking their jobs and personal safety.

Now, four decades later, more than a dozen Vermont towns, from Brattleboro to Newport, hold events for Pride Month each June. This year, Woodstock will join the ranks. Pride of Woodstock, running from Thursday, May 30, to Sunday, June 2, will include a high-heel race; drag brunch; and LGBTQ-themed trivia, movies and comedy shows.

"We have the infrastructure; we have a very progressive community," festival cochair Gabe DeLeon said. "So why not Woodstock?"

Two movie screenings will kick off the fest on Thursday: Codependent Lesbian Space Alien Seeks Same, a 2011 indie comedy, chosen by the Queer Straight Alliance at Woodstock Union High School, about three lesbian space aliens finding love on Earth; and The Birdcage, a 1996 film about a gay Miami drag club owner who pretends to be straight when he meets his daughter-in-law's father, an ultraconservative Republican senator.

On Friday night, the Woodstock Inn will host cocktails and hors d'oeuvres at a welcome reception on the inn's front lawn, followed by a dance party at the Village Inn. Both events are free, with a cash bar.

Moving into the weekend, fest-goers can strut their stuff at a high-heel race on Saturday morning. Participants are encouraged to "run, walk, saunter or sashay" the roughly 1,000-foot course. The top three finishers will win prizes, including a snowboard for the first-place winner. For those planning on wearing stilettos, fear not: There will also be awards for best hair, shoes and outfit.

DeLeon said his husband is leaning toward a more practical chunky heel — though it's "an ill-advised seven inches."

In the afternoon, browse arts and crafts made by 35 local vendors at the Made With Pride fair. There, the Queer Straight Alliance will host an open mic, where participants can sing, recite poetry or act out a skit.

• Courtesy
• Pride brunch

A brunch at the Woodstock Inn on Saturday morning, for $75 per person, will feature three drag performers: Rutland queen Amy Leigh Celestial, along with Saiyohni Gray and Vicky Sparkle-Titz, both of whom are flying in from the Bay Area.

DJ Bugie, another San Francisco-based entertainer, will provide the tunes for Tea Dances at East End Park on Saturday and Sunday afternoons. In New York in the 1950s and '60s, gay singles met up at so-called "tea dances" at a time when serving alcohol to gay people was illegal. (The sober Sunday afternoon dances also allowed attendees to be ready for work on Monday morning.)

"A lot of us Vermonters are early birds," DeLeon said. "So we can get our dancing out of the way, grab a bite and then go to sleep early."

For those who want to stay up, the fun continues at Richardson's Tavern at the Woodstock Inn. Jesse Plotsky and Owen Daniel-McCarter, co-owners of the LGBTQ-friendly Babes Bar in Bethel, will host gay trivia.

Concluding the fest on Sunday, "Funny With Pride" will feature four LGBTQ comedians: Vicki Ferentinos, a top-three finalist in the 2022 Vermont's Funniest Comedian contest; New York City comic Shawn Hollenbach; and New Hampshire comics Kevin McTaggart and Will Berman. Hollenbach created and hosts "Closet Cases," a live show at the Stonewall Inn in NYC — the site of the 1969 riots that launched the modern gay rights movement — where comedians share their coming out and transitioning stories.

Seton McIlroy, co-organizer of the fest and chair of the Woodstock Village Board of Trustees, said she's proud of the message the festival will send to her nonbinary child.

"I want to show them that there is a community and that there are people out there who are just like they are," McIlroy said. "This is something to be celebrated."

Woodstock, the Upper Valley tourist destination with a nostalgic Americana feel, can sometimes be stereotyped as stuffy, she added. She hopes the inaugural festival can challenge those perceptions, she said, and that Pride of Woodstock will become an annual tradition.

Pride and Joy

While Vermont hosts more Pride events than we can list here, read on for six other highlights this May and June. Burlington hosts its annual Pride celebration in September, when students are back in town for the fall semester. For a more comprehensive list, see gayvermont.org.

Montpelier Pride Fest: This six-day Capital City celebration includes a dance party on the Statehouse lawn, a parade, a screening of the documentary Before Stonewall and a queer erotic poetry reading. Wednesday, May 29, through Wednesday, June 5. pridecentervt.org

Essex Pride: In its second year, Essex's fest features a parade, drag story hour with local queens Emoji Nightmare and Katniss Everqueer, and a roller skate disco party. Friday, May 31, and Saturday, June 1. essexvtpride.org

St. Albans Pride Weekend: Catch a fireworks display at the conclusion of this inaugural three-day celebration, featuring a drag show, parade, and family-oriented picnic and barbecue. Friday, June 7, through Sunday, June 9. pridecentervt.org

Bethel Pridefest: Home to Babes Bar, the mecca of Green Mountain State LGBTQ nightlife, this central Vermont town will host trivia night, a "masQUEERade" dance and a drag show with Emoji Nightmare. Thursday, June 27. instagram.com/bethelpridefest

Barre Pride Fest: Packed into a single day, this show of Pride includes a bake sale, bike ride, drag queen story hour and lots of rainbow flag waving. Saturday, June 8. pridecentervt.org

Rutland County Pride Festival: The party kicks off with a "Juneteenth strut" at the Rutland Free Library, followed by a celebration with food, games and drag queen performances. Saturday, June 22. rcpride.org