The Jenny Wiley Festival is Prestonsburg’s signature fall celebration, held each October in the heart of downtown. Since 1982, it has brought together families, friends, and visitors for four days of community spirit, entertainment, and fun. The festival features a lively mix of carnival rides, arts and crafts from regional artisans, food vendors, parades, car shows, and plenty of live music and performances. Beloved traditions, like the arrival of the “Pumpkin Man” with his award-winning giant pumpkins, add to the charm and hometown feel. Drawing thousands each year, the Jenny Wiley Festival is a vibrant showcase of local culture and creativity—an event that truly offers something for all ages.