Pineville & Bell County KY Events Calendar
Things to do in Pineville, Middlesboro and the Cumberland Gap area this weekend and beyond.
First Friday Luncheon
A monthly community luncheon held on the first Friday of the month.
November 6, 2026
Middlesboro City Hall, Middlesboro
November Lunch & Learn
A professional networking and educational event featuring EKU President McFadden.
November 6, 2026
Bell County Chamber of Commerce, Pineville
Annual Christmas Bazaar
An annual holiday market event featuring various vendors and crafts.
November 7, 2026
The Corbin Arena, Corbin
Bell County Board of Health Meeting
A public meeting held by the Bell County Board of Health to discuss local health matters.
Tuesday, November 10, 2026
Bell County Health Department, Pineville
Recipe Exchange
A community gathering to share favorite recipes and culinary tips.
November 12, 2026
Bell County Cooperative Extension Service, Middlesboro
Corbin Arena Worship Gathering
A community worship gathering held at The Corbin Arena.
November 14, 2026
The Corbin Arena, Corbin
Middlesboro 4-H Club at SKCTC
A meeting for the local 4-H club members held at the Southeast Kentucky Community and Technical College.
November 18, 2026
SKCTC, Middlesboro
Bell County Cloverbuds
A youth development program meeting for younger 4-H members.
November 19, 2026
Bell County Cooperative Extension Service, Middlesboro
Tinsel Trail on the Avenue
A festive winter tradition where downtown comes alive with beautifully decorated Christmas trees along the Levitt Lawn, creating a magical holiday stroll for families.
November 20, 2026 - December 31, 2026
Levitt Lawn, Middlesboro
Laugh and Learn
An educational and social program hosted by the Extension office.
November 20, 2026
Bell County Cooperative Extension Service, Middlesboro
Make your own Charcuterie Board and Spatulas Workshop
A hands-on workshop where participants create their own charcuterie boards and spatulas.
November 20, 2026
LMU Center for the Arts, Cumberland Gap
Holiday Gatherings in Pineville
Pineville hosts various seasonal holiday events including tree lightings, parades, and downtown holiday markets throughout the late November and December season.
Late November through December 2026
Downtown Pineville, Pineville
First Friday December: Stay Late to Eat & Shop
Enjoy extended hours at local shops, restaurants, and small businesses while exploring the charm of the Gap.
December 4, 2026
Town Of Cumberland Gap, Cumberland Gap
45th Victorian Christmas
A beloved holiday tradition featuring old-fashioned charm and festive activities in the town of Cumberland Gap.
December 5, 2026
Town Of Cumberland Gap, Cumberland Gap
Middlesboro Christmas Parade & Tree Lighting
Annual nighttime Christmas Parade and Tree Lighting along historic Cumberland Avenue in downtown Middlesboro featuring holiday floats, marching bands, music, and Santa.
Saturday, December 5, 2026
Downtown Middlesboro, Middlesboro
Visions of Christmas Past
A festive afternoon featuring ornament and cookie decorating, hot chocolate, and a visit with Father Christmas.
December 5, 2026
Abraham Lincoln Library and Museum, Harrogate
Cole Chaney & KYOVA with Abbie McAllister
A live music performance featuring Cole Chaney and KYOVA with special guest Abbie McAllister.
December 5, 2026
Local Venue, Pineville
Stained Glass Ornaments Section 2
A creative workshop to make stained glass ornaments.
December 8, 2026
LMU Center for the Arts, Cumberland Gap
Recipe Exchange
A community gathering to share favorite recipes and culinary tips.
December 10, 2026
Bell County Cooperative Extension Service, Middlesboro
Make Your Own Wooden Christmas Tree
A workshop to craft your own wooden Christmas tree decoration.
December 11, 2026
LMU Center for the Arts, Cumberland Gap
Christmas Market and Parade
Celebrate the season with a joyful day full of festive fun, local shopping, and small-town Christmas spirit.
December 12, 2026
Town Of Cumberland Gap, Cumberland Gap
Cumberland Mountain Music Christmas Show
A holiday-themed live music show featuring bluegrass, gospel, and traditional mountain music.
December 12, 2026
Cumberland Gap Convention Center, Cumberland Gap
School Half Day
A scheduled half-day for local schools in the Pineville area.
Friday, December 18, 2026
Local Schools, Pineville
Last Chance Before Christmas
A festive day of holiday shopping and celebration perfect for wrapping up your Christmas list.
December 19, 2026
Town Of Cumberland Gap, Cumberland Gap