Festivals in Middlesboro, KY.
Festivals, Family & Kids Festivals
53rd Berea College Celebration of Traditional Music
October 9 - 11, 2026
Annual Celebration of Traditional Music
(859) 985-3472
Berea College - Berea, KY Or Online at vimeo.com/bereacollegemusic
The 53rd annual Berea College Celebration of Traditional Music will take place on Friday, October 9 through Sunday, October 11, 2026, celebrating home-made music as passed on from person to person in the Appalachian region and the musicians who play it. Concerts, jams, Gospel sing, dance, workshops, Dinner-on-the-Grounds symposium occur at several venues across campus. KidZone Saturday at the Madison County Library in Berea. All events are free to students. Performers include The Brandenberger Family, The Resonant Rogues, Elizabeth LaPrelle and Brian Dolphin, Elizabeth McCorvey, and Lifetime Achievement Awardee Stephen Seifert.
Winterfair!
December 4 - 5, 2026
allpeoplesuu.com/community/connections/wint..
(502) 905-4408
All Peoples UU - Louisville, KY
WinterFair! presents over 70 artists in two church buildings (plus Bold & Cold artists outdoors!). All original handcrafted media including ceramics, wood, mixed media, fiber, photography, sculpture, glass, jewelry. NEW Artists: Two Jury Sessions: Summer Early Bird: deadline 7-1-26 Fall Final Jury: deadline: 8-31-26 See instructions on requirements to Jury on the website listed above. Food, including vegetarian, soups, chili, jumbo hot dogs and homemade desserts. Art raffle supporting a worthy local charity.
Events in Middlesboro, KY — upcoming
October 2 - 3, 2026
Cumberland Mountain Fall Festival
Downtown, Middlesboro, KY
Status: Updated 8/18/2026
This Kentucky Festival will have crafts, fine art and fine craft exhibitors, and 10 food booths. There will be 1 stage with National, Regional and Local talent and the hours will be . This event will also include: antiques, carnival, car show.
