Pineville & Bell County KY Events Calendar
Things to do in Pineville, Middlesboro and the Cumberland Gap area this weekend and beyond.
Pine Mountain State Resort Park Daily Operations
Pine Mountain State Resort Park offers year-round access to hiking trails, golf, and lodge dining, including the historic lodge and scenic mountain views.
Ongoing daily operations
Pine Mountain State Resort Park, Pineville
Rides4Fun Getaway at Pine Mountain State Resort Park
The final day of the Rides4Fun Getaway event featuring outdoor activities and gatherings at the park.
September 28, 2026
Pine Mountain State Resort Park, Pineville
Pine Mountain State Resort Park Hiking and Nature Exploration
Visitors can enjoy year-round access to the park's extensive hiking trails, including the scenic paths near Chained Rock and the Kentucky Ridge State Forest.
Daily throughout September and October 2026
Pine Mountain State Resort Park, Pineville
Levitt Amp Music Series
The final installment of the weekly summer concert series held in downtown Middlesboro, featuring live music performances.
Thursday, October 1, 2026
Downtown Middlesboro, Middlesboro
Sip, Shop, and Savor
An evening event in downtown Pineville featuring local shopping, dining, and community engagement.
October 1, 2026
Main Street Pineville, Pineville
Cumberland Mountain Fall Festival
An annual community celebration featuring arts and crafts, local food vendors, live entertainment, and family-friendly activities in the crisp autumn air.
October 2026
Downtown Middlesboro, Middlesboro
Cumberland Mountain Fall Festival
A community festival held in downtown Middlesboro featuring a music lineup and various festivities.
October 2-3, 2026
Downtown Middlesboro, Middlesboro
Hunter Flynn Concert
A live country music performance held in downtown Middlesboro.
October 2, 2026
Discover Downtown Middlesboro, Middlesboro
SOAR Summit
A regional summit focused on economic development and innovation in the Appalachian region.
October 7, 2026
The Corbin Arena, Corbin
Moonshiners Ball 2026
An annual music and arts festival featuring a diverse lineup of performers in a scenic Kentucky setting.
October 8-11, 2026
Kentucky State Parks, Kentucky
Bell County Pride Festival 2026
An annual pride festival celebrating the community in the Bell County area.
October 10, 2026
Pineville, Pineville
LAUNDRY DAY Presents: The Larger Than LIFE Tour
A live music performance featuring the band LAUNDRY DAY as part of their Larger Than LIFE tour.
Wednesday, October 14, 2026
Barley's Taproom and Pizzeria, Middlesboro
Porchfest 2026
A local music event featuring performances on various porches throughout the community.
October 16-17, 2026
Pineville, Pineville
1st Annual Fall Festival
A community-focused fall festival featuring seasonal activities, local vendors, and family-friendly entertainment.
October 17, 2026
Corbin Community Venue, Corbin
Fire Tower Campout
An overnight camping experience at the fire tower, offering a unique perspective of the park and surrounding landscape.
October 17-18, 2026
Pine Mountain State Resort Park, Pineville
Josiah and the Bonnevilles
A live concert performance by the band Josiah and the Bonnevilles at the historic Bell Theater.
October 17, 2026
Bell Theater, Pineville
Josiah and the Bonneviles at the Bell Theater
A live musical performance by Josiah and the Bonneviles hosted at the historic Bell Theater.
October 17, 2026
Bell Theater, Pineville
Magoo Live Performance
A live music event featuring the artist Magoo at Barley's Taproom and Pizzeria.
Tuesday, October 27, 2026
Barley's Taproom and Pizzeria, Middlesboro
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
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Light Up Pine Mountain
Join the community for the annual tree lighting ceremony, singing, and family fun in downtown Pine Mountain.
November 13, 2026
Downtown Pine Mountain, Pine Mountain
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
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
Tinsel Trail on the Avenue
A festive winter tradition where downtown Middlesboro comes alive with beautifully decorated Christmas trees displayed along the Levitt Lawn.
December 2026
Levitt Park, Middlesboro
Christmas Parade
A beloved local tradition featuring families, local organizations, and marching bands celebrating the holiday season.
December 5, 2026
Downtown Pine Mountain, Pine Mountain