For people who want to celebrate Pride Month in the Upper Valley, there is a growing array of options. It’s easy to find an inclusive movie screening or bookstore talk, and there are larger annual events, including at Dartmouth College and White River Junction.

But for Woodstock residents, this means traveling at least 20 minutes, a surprising notion considering Woodstock’s tolerance and its enthusiasm for town-wide events such as Wassail Weekend and the Alumni Parade.

That is, until last year, when Gabe DeLeon decided to take matters into his own hands and create Woodstock’s first Pride celebration, slated for this weekend.

“It started as a conversation between friends — we were discussing what we were all going to do for Pride that year, since Woodstock didn’t have its own celebration,” said DeLeon, 60. “I got curious about other Prides in the area and did some research; about a dozen municipalities in Vermont do something every year, even if it’s as basic as a community picnic. It became apparent that there was an opportunity to do something important here, and so Seton (McIlroy) and I started looking into what it would take to put on Woodstock’s first Pride.”

Woodstock’s inaugural celebration of Pride Month will begin Thursday evening, with a 5 p.m. screening of “Codependent Lesbian Space Alien Seeks Same” in the Billings Farm Theater and a 7:30 p.m. screening of “The Birdcage” in Town Hall Theatre, films chosen by the Woodstock Union High School Queer Straight Alliance (QSA), and run through Sunday, June 2.

Events include a Friday night dance party at the Village Inn; Saturday morning High Heel Race on Elm Street followed by a Drag Brunch at the Woodstock Inn.

Chief organizers DeLeon, who works as the assistant to the president at the Woodstock Inn, and Seton McIlroy, 45, who is the chair of the Woodstock Village Board of Trustees, have been hard at work since May 2023 to stimulate a Pride movement in Woodstock.

After taking stock of Woodstock’s public infrastructure to support such an event, including the town’s green spaces and theaters, DeLeon and McIlroy began to gauge support among elected officials, business leaders, organizations and community members, armed with a laundry list of event ideas and spreadsheets.

Once it was clear that there was considerable interest in the community, they started planning.

“It was a little daunting to take on the logistics,” DeLeon said. “We estimated that we would need about $30,000 to pull this off. And I mean, I’ll tell you, it’s a lot of work. We were really going to need to band together with the community.”

Not only does the budget required for a sizable celebration necessitate dedicated fundraising efforts, but negotiating with the town’s tapestry of community leaders and organizations is a job for someone informed on event policies and local politics. DeLeon and McIlroy were well positioned to rise to the occasion.

Despite the amount of work involved in raising money, organizing volunteers and securing permits, DeLeon had plenty of energy to push through.

“It’s my nature to take on challenges. And it’s the right thing to do.” he said. “It’s about celebrating individuality in a welcoming and supportive environment, allies and LGBTQ+ alike.”

And when called upon, the community answered, DeLeon said. After DeLeon and McIlroy made their case to the Woodstock Economic Development Commission (EDC), they were granted $3,000 to fund the High Heel Race. The Woodstock Inn, where DeLeon works, agreed to host three of the Pride events, including welcome cocktails, the drag brunch, and trivia night. The Woodstock History Center and Pentangle Arts contributed equipment. Chief Joe Swanson of the Woodstock Police Department helped to navigate the logistics of following ordinances and closing Elm Street for two hours for the High Heel Race. And the owners of Babes Bar in Bethel, Jesse Plotsky and Owen Daniel-McCarter, agreed to host trivia night.

LGBTQ+ comedians Vicki Ferentinos, ex-owner of Soulfully Good Café, Shawn Hollenbach, Kevin McTaggart and Will Berman will perform stand-up comedy at the Grange Theater on June 1.

“Many other citizens have been extremely involved with getting the word out along the way, donating gifts, and offering their spaces to hold events. It’s genuinely been a community-wide effort, which makes it even more special,” said DeLeon. “We’re also getting a lot of people who want to volunteer and it’s wonderful, we want to keep them coming, because we’ll need them for the weekend. Moving things around, setting tables up, getting crafts together. Right now, although we’re almost there, we’re still a couple thousand dollars short, which means we’re focusing on contacting donors and sponsors.”

Charitable giving is also part of DeLeon and McIlroy’s agenda. The High Heel Race, considered the “crown jewel” of the weekend, provides an opportunity for sponsorship, and some of the proceeds will go to Woodstock High School’s QSA after operations costs.

“It’s going to be like the Kentucky Derby; all about the pageantry. The race itself is over in three to five minutes. It’s really all about what happens before,” said DeLeon.

The race spans 1,000 feet of Elm Street from Pleasant Street to Central Street. Festivities begin at 9:30 a.m. on Saturday, the race starts at 10:30, and by 11, the street will be open again.

An awards ceremony is planned on the Green, with winners selected in six categories: First Place, Second Place, Third Place, Best Hair, Best Shoes and Best Outfit. “Costumes, wigs, makeup, and sparkles are highly recommended,” touts the Pride of Woodstock’s web page, which features a custom logo for the event designed by Doug Blanchard, another in a long list of local contributors.

DeLeon reflected fondly on the year, despite its challenges. “People I knew, I now know better. People I just met that have unexpectedly unbelievable backgrounds have lent their support. But most importantly, we have people that didn’t know each other who are now working together to make this happen. If anything, the community, which I already knew worked well together, is going to be a lot closer after this.”

Looking to the future, DeLeon said that he isn’t sure how things will unfold in future years, adding that it depends how this Pride is received and what turnout is like. He is hopeful, however, that this year’s celebration will open the door for more inclusive spaces.

For more information about tickets and volunteer opportunities go to woodstockvt.com/pride-of-woodstock-vermont.

Caoimhe Markey is a freelance writer. She lives in Woodstock.