Thanks in large part to Daniel Boone's explorations, pioneers were able to cross the Cumberland Gap as they traveled the Wilderness Road to the West. Today, Cumberland Gap is one of the largest national historical parks in the country, with territory in Virginia, Kentucky and Tennessee. (The headquarters is in Middlesboro, Kentucky.) The park, which is in the far southwest corner of Virginia, offers interpretive exhibits, hiking, camping, picnicking and backcountry outings (permits required). Cumberland Gap is highly recommended for its historical importance and its scenic beauty.
If you have time, hike along the Ridge Trail on Brush Mountain to the Hensley Settlement. This community of farmsteads prospered in near isolation for almost 50 years. (You can also take a shuttle to Hensley Settlement, but the hike is beautiful if you're up for it.)
If you're looking for a place to stop on your way to the Cumberland Gap, consider Abingdon, home of the famous Barter Theatre. It was founded during the Depression by a group of actors who staged performances in exchange for food. Such famous actors and writers as Gregory Peck, Hume Cronyn and Tennessee Williams filled their bellies courtesy of the Barter. The Virginia Creeper Trail is a 34-mi/55-km hiking, biking and equestrian trail that follows an old railroad bed. You can take it southeast to the small village of Damascus, near the Tennessee border. The Appalachian Trail that runs from Georgia to Maine also passes through this area. West of Abingdon on Highway 58 (the best route to Cumberland Gap from Interstate 81) is Big Stone Gap, where you can see the historical drama The Trail of the Lonesome Pine.
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