Woodstock, Vermont’s Annual Pride Celebration Returns
If you’d like to avoid the craziness this Pride but still bond with the LGBTQ+ community, consider Pride of Woodstock, Vermont, June 6-8, 2025.
Rooted in community, inclusivity and creativity, Pride of Woodstock, Vermont announces the return of the second annual Pride celebration taking place from June 6 through 8, 2025. Drawing in more than 400 attendees in its debut last year, the festival – designed to celebrate love in all forms – aims to build on the momentum and town’s year-round Pride spirit with another festive-filled weekend including the popular high heel race and local artisan craft fair.
“We’re looking forward to bringing the Pride of Woodstock festival back for a second year, with the addition of new events including costume contest at Pentangle and a play at Artistree. Our inaugural event was filled with so much love and joy, it was clear just how meaningful this celebration was to our community,” says Seton Mcilroy, Pride of Woodstock, Vermont co-chair. “Pride of Woodstock is more than a festival though. It’s a reflection of the inclusive spirit that makes our town so special.”
The celebration will commence with a welcome reception on the front lawn of the historic Woodstock Inn & Resort on June 6 from 5pm – 7pm, where attendees can mix and mingle over cocktails and small appetizers crafted by the Inn’s culinary team. The evening will continue at the Little Theater from 9 p.m. to midnight with music by local DJ B.
On Saturday, June 7, the festivities are marked by several standout events that highlight both collective creativity and community spirit. Beginning at 9:30am, the High Heel Race on Elm Street rolls out the red-carpet for participants as they run, strut, and stroll their way along the one-eighth mile dash through the Village of Woodstock. Prizes will be awarded for race winners, plus those with the best high heels, costumes, and hair. All festival attendees can register to participate ($40 per person), with all proceeds benefiting the local Woodstock Union High School’s Queer-Straight Alliance.
Close by, on the Woodstock Village Green in the center of town, the “Made with Pride” Arts and Crafts Fair will be open from 10am – 3pm, showcasing handmade items from local LGBTQ+ artists and ally maker community. Attendees can peruse the booths of local and regional artisans, including Wild Woogs, known for handcrafted, upcycled fabric sculptures with a whimsical twist; Melissa Tabas, showcasing one-of-a-kind, handmade clothing made of vintage blankets and linens; and Something Wonderful Shop, offering an eclectic mix of gifts from charms and patches to custom candles. Plus, visitors can sip and sample from an array of local vendors such as Ramunto’s Pizza, Ranch Camp Burritos, and Abracadabra Coffee.
Back by popular demand, the Pride of Woodstock Drag Brunch will take place at the Woodstock Inn & Resort that day. Doors open at 11:30 AM, with the 90-minute performance beginning promptly at 12 PM hosted by six captivating performers. The brunch menu, crafted by the resort’s Executive Chef Matthew McClure, will be served buffet-style and include a welcome beverage choice of mimosa, bellini, prosecco, or NA Sparkling Tost.
Additional events and activities range from an afternoon tea dance party with music by DJ Bugie to a Funny with Pride comedy showcase, where comedians such as Will Pupura, Bailey Pope, and Woodstock local Vicki Ferentinos take the stage at the Woodstock Town Hall Theater. Tickets can be purchased online here for $25 per person.
Beyond this annual marquee celebration, Pride of Woodstock 365 offers support and opportunities for community connection, year-round. Each month, the organization and its partners feature programs, activities, and sessions designed to foster a more inclusive, welcoming, and supportive environment. Covering a wide range of topics – from mental health in the LGBTQ+ community to educational workshops and social gatherings – this ongoing series ensures that the spirit of Pride continues in Woodstock, Vermont, all year long.
Sponsors of Pride of Woodstock include Woodstock Inn & Resort, Farmer and the Bell, Ramunto’s Brick & Brew Pizza, Jasper & Prudence, Mascoma Bank, and Green Mountain Foundation. Pride of Woodstock, Vermont is a project of Woodstock Community Trust, a 501c3 organization.
About Pride 365 and Pride of Woodstock
Pride of Woodstock, Vermont is a celebration of love, diversity, and community in the charming New England town of Woodstock, Vermont. More than an annual weekend of events in early June – the organization reflects the town’s commitment to inclusivity with Pride of Woodstock, Vermont 365’s monthly programs that support an accepting presence year-round. Pride of Woodstock, Vermont fosters an environment where everyone feels welcome, supported, and celebrated. Pride of Woodstock, Vermont is a project of Woodstock Community Trust.
About Woodstock, Vermont
Woodstock, Vermont is a year-round destination located on the banks of the Ottauquechee River and at the crossroads of the Vermont Scenic Byway. Tucked in the Green Mountains of Windsor County, Woodstock is home to the only national park in Vermont and three historic covered bridges. The charming main street in the village welcomes you to shop and dine or you can enjoy some of the most colorful seasons and exciting outdoor activities in New England.
