About Old Fashioned Trading Days in Williamsburg, KY
Old Fashioned Trading Days is the signature annual street festival in Williamsburg, Kentucky, transforming the historic Whitley County Courthouse Square and Main Street into an open-air Appalachian marketplace every September. For over four decades, the three-day celebration has drawn thousands of visitors across southeastern Kentucky for free live music, regional arts and crafts, heritage demonstrations, and festival food.
2026 Recap & 2027 Planning Dates
In 2026, Williamsburg celebrated the 43rd Annual Old Fashioned Trading Days from Thursday, September 10 through Saturday, September 12, 2026 in downtown Williamsburg. Held annually on the Thursday, Friday, and Saturday following Labor Day weekend, the 44th Annual Old Fashioned Trading Days is projected for September 9–11, 2027 (confirm final 2027 stage lineups with the City of Williamsburg as September approaches). Looking for events happening right now? Visit our upcoming Williamsburg events calendar.
What to Expect on Main Street
- Free Live Bluegrass, Gospel & Country Music: Main stage concerts run throughout all three days with zero admission charge.
- Artisan, Craft & Antique Vendors: Well over a hundred booths line Main Street and Courthouse Square offering handmade woodwork, quilts, jewelry, soaps, and Appalachian crafts.
- Classic Southern Festival Food: Funnel cakes, smoked barbecue, pulled pork, roasted corn, Kettle corn, and homemade desserts.
- Car Show, Contests & Family Activities: Antique car and truck shows, school spirit events, and family games.
Visitor Information & Official Contacts
- Location: Whitley County Courthouse Square & Main Street, Downtown Williamsburg, KY 40769 (take I-75 Exit 11 and follow KY-92 E / US-25W into downtown).
- Admission: Free to the public.
- Official Organizer Contact: City of Williamsburg / Old Fashioned Trading Days Committee — (606) 549-6033 or williamsburgky.com.
