‘Pride of Woodstock’ receives high heels race permit

By Lauren Dorsey, Staff Writer

At the Woodstock Village Board of Trustees meeting on Tuesday night, the trustees unanimously approved a permit for a high heels race on June 1, and banners on either side of The Green, which will hang from May 27 through June 3. Both permits are part of the festivities planned for the Village’s first-ever Pride of Woodstock, a pride celebration slated for the first weekend of June. Presenting both permit requests, Seton Mcllroy stepped out of her usual role as chair of the trustees and into her shoes as the co-chair of Pride of Woodstock. Mcllroy abstained from voting on either request.

The idea for Pride of Woodstock came about last May when Gabe Deleon, who is also a member of the Village Trustees, began talking with his friends about organizing something to celebrate Pride in 2023. Although by that point, it was too close to June to put on anything elaborate, Deleon quickly realized that there was plenty of support around town to create a formal, annual celebration, so they just needed to get the ball rolling, Deleon said. Together with Mcllroy, Deleon has built a task force of volunteers to begin making a Woodstock Pride celebration a reality. They hope to put on a variety of events, which could include everything from a drag brunch to a trivia night, spread throughout the weekend.

The team chose the first weekend of June for the festival partly because of the relatively limited tourist traffic Woodstock has historically seen that weekend, aside from the Covered Bridges Half Marathon scheduled for Sunday morning. The festival’s overlap with the marathon may even help their setup for the high heels race, as Mcllroy mentioned in the meeting that they may be able to reuse some of the marathon’s barriers.

Mcllroy estimates that the high heels race will take roughly two minutes. “Some people might strut, and if they strut instead of run, it could be a little [longer],” said Mcllroy. The race course, entirely on Elm Street downtown, will be under 1,000 feet, beginning near the intersection of Elm and Pleasant Street and ending just before the intersection of Elm and Central Street at the crosswalk in front of Vermont Flannel. According to the permit, Pride of Woodstock is expecting roughly fifty participants for the event, although Mcllroy wants to ensure, even at this early stage, that everyone feels invited. “I like to think that the high heel race will be the crown jewel of the weekend,” said Mcllroy. “Everybody is welcome to run in the race, men, women, straight, gay, whatever. We’re all here for it. [Anybody] can also come out and cheer on the sidelines.”

The team also plans to set up pickup trucks on each end of the race route, which will act as stages so that presenters can do commentary as racers cross the finish line. McIlroy said they only plan to close Elm Street down for about two hours for the race in the hopes that moving in and out quickly will help reduce the event’s disruption of any other village activity. After the race’s conclusion, they plan to move the festivities to The Green, where they will top off the event with an awards ceremony.