With autumn underway in the Crater City, the City of Middlesboro and community partners are preparing for the city's signature winter holiday traditions along Cumberland Avenue.
Holiday Events Lineup
- Small Business Saturday (Nov 28, 2026): Local shops and restaurants along historic Cumberland Avenue offer holiday specials.
- Tinsel Trail on the Avenue (Opening Dec 4, 2026): Community organizations and local businesses decorate live Christmas trees along the Levitt Lawn downtown for families to stroll through all month.
- Middlesboro Annual Christmas Parade & Tree Lighting (Dec 5, 2026): Floats, marching bands, and Santa Claus parade down Cumberland Avenue followed by the official lighting of the city Christmas tree.
- Town of Cumberland Gap Christmas Market & Parade (Dec 12, 2026): Just through the Cumberland Gap Tunnel, historic Cumberland Gap hosts its holiday market and evening parade.
For parade registration details or tree sponsorship information, contact Middlesboro City Hall at (606) 248-5670 or the Bell County Chamber of Commerce at (606) 302-4522.
Buy Maps
