Cumberland Gap National Historical Park
Southeastern Kentucky stretches into the Cumberland Mountains, with the Cumberland Gap serving as the most major route across the hills. Native Americans exploited this 760-foot-deep cut through the range as a trade route, which was found by pioneers going west in the mid-18th century.
More than 200,000 white settlers crossed the Cumberland Mountains to the west when the renowned Daniel Boone drove his Wilderness Trail into Kentucky in 1775. In Middleboro, the Visitor Center has a small interactive museum and rangers on staff to answer questions. You may also take a shuttle excursion from the visitor center to the Hensley Settlement, a well-preserved old country settlement. The park also provides guided hiking excursions of Gap Cave, with a popular hike to Pinnacle Overview, which gives spectacular views of the hills and the Gap from an altitude of 2460 feet.
Address: 91 Bartlett Park Road, Middlesboro, Kentucky
Website: http://www.nps.gov/cuga/index.htm