Ashland Pride Festival

Ashland Pride is a small-town Pride festival in Ashland City Park south of Columbia, organized by Caitlin Cunningham of the Dandy Lion Cafe with volunteers. The day includes a 5K run, a parade on Ash Street, a youth area, vendors, live music, and drag and other stage performances.

Ashland's Pride Festival is a one-day event that has run from 8 a.m. to 3 p.m. in Ashland City Park, starting with the 5K and moving into a parade and an afternoon of activities. The parade travels along Ash Street, and spectators are welcome to step in and join it at any point, whether on foot or on roller skates. Attendees have mentioned that the park's shade makes for a comfortable setting.

Caitlin Cunningham, owner of The Dandy Lion Cafe, both organizes the festival and performs in it, appearing in a showcase by Muse Pole Fitness performers. The stage program has also featured live music and a drag show with a local performer as emcee, who described the day as a chance to show queer joy and let people see there is no need to be afraid to be queer. Lawn games such as cornhole keep the park busy between sets. The Boone County Journal, the local weekly for Ashland and Hartsburg, covered the festival in its fifth year.

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.

Ashland Pride Festival has included parade, festival, 5k and youth events.

The organizer has not announced dates for 2027 yet. In 2026 it was held July 18, 2026. It usually falls mid-July Saturday.