Regarded as the first gateway to the western frontier, Cumberland Gap was first used by the animals as they migrated from one corner of the continent to another in search of food, then the Native Americans, and later by Dr. Thomas Walker, Daniel Boone and other frontiersmen. The early explorers followed well-worn bison and Indian trails through the narrow opening, and entered into the land of Kentucky, a self-described wilderness that was soon open to the first great wave of westward migration. Throughout, the newcomers had to brave the elements of nature, battle or evade capture from the Indians and cross large bodies of water.
There are over 70 miles of trails at Cumberland Gap National Historical Park, ranging from the Ridge Trail that wanders through the backcountry along the spine of the mountains, to the notorious White Rocks Trail that gains 3,000 feet in elevation. The Hensley Settlement Trail accesses historic Hensley Settlement, while the Pinnacle Trail offers breathtaking views and a steep ascent. The Tri-State Peak Trail leads up to Tri-State Park, where Virginia, Kentucky and Tennessee converge at a single point, while the Wilderness Road Trail recounts the journey that the settlers once took across Cumberland Gap along the former US 25E roadbed that has since been reclaimed.
The 16.5 Hensley Settlement-White Rocks Loop features a one or two-night trip to Hensley Settlement, Sand Cave and White Rocks.
The route through the Cumberland Gap was first brought to the attention of travelers by Dr. Thomas Walker, who had been hired to stake out an 800,000-acre grant beyond the Blue Ridge Mountains in Virginia. In 1750, hired by the Loyal Land Company as a surveyor, he and five others recounted the importance of the gap as there was little option to cross the great divide back then. While there were other openings further up the range, they were blocked by more mountains behind and other natural barriers that made going any further too difficult or impossible. This paled to Cumberland Gap, where after crossing it into Kentucky, the traveler was greeted by the Cumberland River and the “Narrows,” which allowed those to travel out of the rugged mountain system of the south. From there on north, it was relatively smooth sailing.
Walker was followed twenty-five years later when Daniel Boone, a renowned pioneer, crossed the gap with 30 others to mark out the Wilderness Trail. Read more about the history of Cumberland Gap »