Built entirely within the impact crater of a meteorite, the Kentucky Trail Town of Middlesboro captures the distinct flavors of The Kentucky Wildlands with such attractions as Cumberland Gap National Historic Park, The Coal House (a home built only with bituminous coal) and the 1890 grand Victorian Cumberland Manor Bed & Breakfast. Annual events, such as the Wing Fling Hot Wing Festival and the summertime Levitt Amp Middlesboro Music Series (featuring weekly crater-filling concert performances), add to its charm, along with local favorites like Shades Café & Steakhouse and the A.D. Campbell Co. women’s clothing boutique, one of Middleboro’s oldest and trendiest downtown businesses.
Complete your adventure with a short drive to the Cumberland Gap National Historic Park and enjoy more than 85 miles of hiking trails, including the breathtaking views of the 1,800-foot Pinnacle Overlook (accessible by foot and bike). Visit the nearby Corrigan Wildlife Management Area with more than 54,000 acres of fishing, hiking, hunting, and camping, and the Shillalah Creek Wildlife Management Area, which has its own ample hunting, hiking, camping, and fishing and is home to one of only two Kentucky streams for native brook trout fishing.
Up the road lies Pineville with its historic Main Street, artisan shops and art deco Bell Theater and Playhouse. Nearby Pine Mountain State Resort Park, Kentucky’s historical first state park, features the Chained Rock Trail, waterfalls, Laurel Cove Amphitheater, golfing, charming stone and wood lodge, restaurant, and cottage rentals.
Popular Destinations in the Kentucky Wildlands
Two Places Worth Adding to Your Kentucky Bucket List
The Kentucky Wildlands are home to the majority of certified Kentucky Trail Towns, which connect trail users with beautiful, serene natural environments, such as the Red River Gorge, Cave Run Lake, Breaks Interstate Park, Daniel Boone...