Woodstock PrideFest

Woodstock PrideFest is a weekend of family-friendly events in the McHenry County seat, run by Woodstock Pride. The main day on the historic Woodstock Square opens with a parade and continues with live entertainment, food trucks, vendors and speakers. Weekend events have included a field day and color run, a chalk art walk and a pub crawl.

Woodstock Pride grew out of its first event, Kid's Pride Fest, after which organizers formed the group and began working with the Woodstock Area Chamber of Commerce and Industry. The first annual PrideFest drew thousands of people to Woodstock, and the group also held National Coming Out Day events, a Transgender Day of Remembrance vigil, and social and educational gatherings.

When the pandemic stopped most events in 2020, the group held a Pride Promenade, an LGBTQIA+ take on a parade of homes. The parade and festival returned to the Woodstock Square in 2021, and the promenade became a tradition. Later the group grew to a seven-person board, held its first Gayla, doubled its membership and became an independent 501(c)(3).

In 2025 Woodstock Pride opened a community center, a year-round space for connection, resources and support for LGBTQ+ people and allies across McHenry County. It also brought the NAMES Project AIDS Memorial Quilt to town for remembrance and education, and PrideFest 2025 drew nearly 10,000 people over the weekend.

Pride events celebrate LGBTQ+ people and mark the Stonewall uprising of June 1969. Most combine a parade or march with a festival of performers, community groups, vendors and food.

Woodstock PrideFest has included parade, festival, color run, pub crawl and chalk art walk.

The organizer has not announced dates for 2027 yet. In 2026 it was held June 12-14, 2026. It usually falls second weekend of June, main festival on Sunday.