Join us for the Levitt AMP Middlesboro Music Series, a free, family-friendly summer concert series that transforms downtown Middlesboro into a vibrant gathering place. Held at Levitt Park (20th & Cumberland Ave), this event brings together music lovers of all ages to enjoy live performances, local food vendors, and the charm of our historic downtown.
Levitt Park, 20th & Cumberland Ave, Middlesboro, KY 40965
2025 dates TBA, music starts at 6:30pm
Middlesboro Main Street
A blanket or lawn chair for comfortable seating.
To find parking and grab a good spot.
A renovated hotel offering free breakfast, high-speed internet, and an outdoor pool. Located at 1252 N 12th Street.
A modern, pet-friendly hotel offering free hot breakfast, high-speedinternet, a fitness center, and spacious rooms with microwaves and refrigerators. Located at 1260 N 12th Street.
Kentucky’s first state park, offering 30rooms with private balconies or patios, an outdoor pool, pet-friendly accommodations, and on-site dining at the Mountain View Restaurant. Located at 1050 State Park Road, Pineville, KY 40977.
Just southeast of downtown, the Cumberland Gap National Historical Park spans the borders of Kentucky, Tennessee, and Virginia, offering scenic beauty and deep historical significance. Visitors can explore over 85 miles of hiking trails, visit the panoramic Pinnacle Overlook, and learn about early Appalachian life at the preserved Hensley Settlement. The park’s visitor center near Middlesboro features exhibits, ranger programs, and access to the iconic Gap Cave and Tri-State Peak.