Jenny Wiley Festival

About

Held each October in the heart of downtown Prestonsburg, the Jenny Wiley Festival is running since 1982 and claimed as Kentucky's longest-running, continuous festival. The festival features a mix of carnival rides, arts and crafts from regional artisans, food vendors, parades, car shows, and live music. Over 15,000 people travel from near and far to experience downtown Prestonsburg with its many arts and crafts vendors, local food choices, and free live music.

Details

Type

Festival

Season / Event Date(s)

2nd weekend October 2026

Tags

• craft
• food
• annual