To financially support activities the guild has sponsored the Arts and Crafts booths at the Daniel Boone Pioneer Festival. Guild members started displaying art around the court house square in 1975 and the festival grew from those humble beginnings. Thousands of people come to Winchester Labor Day weekend for the festivities that include music, food, Arts and Crafts on Saturday and Sunday. For the first time in 2021 the Festival was held in Downtown Winchester, and will continue in downtown in 2022.