June 6, 7, 8 —WOODSTOCK—Pride of Woodstock returns with its second annual celebration of LGBTQ+ identity, creativity, and inclusion, launching with a welcome reception on the front lawn of the Woodstock Inn & Resort. More than 400 people attended the inaugural event in 2024, and this year’s festival expands its programming with new events, including a costume contest at Pentangle Arts and a theatrical production at Artistree. The reception will feature cocktails and appetizers prepared by the Inn’s culinary team, followed by a DJ dance party with DJ B at the Little Theater, 54 River St., from 9 p.m. to midnight.
Saturday, June 7, marks a full day of festivities starting at 9:30 a.m. with the High Heel Race on Elm St. Participants are invited to run, strut, or stroll a 1/8-mile stretch in bold footwear and themed outfits. Awards will be given to the top finishers and winners in the best costume categories, including hair, heels, and overall style. Registration is $40 per person, with proceeds supporting the Queer-Straight Alliance at Woodstock Union High School.
Also, on Saturday, from 10 a.m. to 3 p.m., the “Made with Pride” Arts and Crafts Fair will be held on the Woodstock Village Green, featuring work by LGBTQ+ artists and allies. Exhibitors include Wild Woogs, offering upcycled fabric sculptures; Melissa Tabas, with handmade garments crafted from vintage materials; and Something Wonderful Shop, showcasing a range of candles, charms, and gift items. Local food and beverage vendors will include Ramunto’s Pizza, Ranch Camp Burritos, and Abracadabra Coffee.
The festival’s popular Drag Brunch returns to the Woodstock Inn & Resort, with doors opening at 11:30 a.m. and the performance beginning at noon. Hosted by six performers, the event features a buffet brunch created by Executive Chef Matthew McClure, accompanied by a welcome drink, with options including mimosas, bellinis, prosecco, and non-alcoholic sparkling beverages.
Additional programming includes an afternoon tea dance with DJ Bugie and a comedy showcase titled “Funny with Pride,” featuring Will Purpura, Bailey Pope, and Woodstock native Vicki Ferentinos. The comedy event takes place at the Woodstock Town Hall Theatre, with tickets available for $25.
Pride of Woodstock is produced by the Woodstock Community Trust, a nonprofit 501(c)(3) organization. The event is part of the broader Pride of Woodstock 365 initiative, which hosts monthly programming year-round on topics such as LGBTQ+ mental health, educational workshops, and social gatherings designed to foster support and inclusivity.
Sponsors of this year’s festival include Woodstock Inn & Resort, Farmer and the Bell, Ramunto’s Brick & Brew Pizza, Jasper & Prudence, Mascoma Bank, and the Green Mountain Foundation.
For more information, visit: prideofwoodstock.org.
Pride of Woodstock returns June 6–8 to celebrate LGBTQ+ identity, creativity, and community featuring, High Heel Race, arts fair, Drag Brunch, comedy, and more across Woodstock venues.
