One of the nation’s most historic routes, the Daniel Boone Wilderness Trail was blazed by the legendary frontiersman in 1775 from Long Island of the Holston at what is now Kingsport, TN, through the Cumberland Gap of Virginia and into Kentucky. It would become the route for hundreds of thousands of settlers of the western frontier.

Long before Columbus settled America, the Wilderness Trail was a major link in the trail systems of the Indians on the North American continent, used for commerce and raids. Gabriel Arthur, a young indentured servant, was first of record to travel the route and see the Cumberland Gap, a natural break in the mountains. Arthur was sent along the trail in 1674 by the Shawnee Indians to secure a trade agreement with settlers. The next recorded man to see the Gap was Dr. Thomas Walker in 1750.

The most daring effort to colonize the rich lands of the Kentucky River area were those of Colonel Richard Henderson, a Superior Court judge of North Carolina. Henderson decided that the best way to secure the area was to deal directly with the Cherokee Indians. He discussed his plan with friends and they formed the Transylvania Company and solicited the assistance of Boone in negotiating with the Indians and blazing the trail. Boone was no stranger to the Kentucky territory, having made several trips through the area. He wanted to make his home in Kentucky and was quick to accept Henderson’s offer.

They found the Cherokee willing to sell the land between the Cumberland and Kentucky rivers for 5 tons of serviceable goods. Final negotiations were held at Sycamore Shoals (now Elizabethton, TN), an ancient Cherokee treaty ground on the southern bank of the Watauga River, about 15 miles southeast of Long Island on the Holston, a sacred area to the Indians. After the agreement, Boone left for Long Island on the Holston to rendezvous with 30 armed and mounted axmen, among them his brother Squire, and son-in-law William Hays.

On March 10, 1775, Boone led his trail blazers from Long Island to blaze the trail through some 200 miles of wilderness northwest through the Cumberland Gap and into Kentucky.

Boone was born in Pennsylvania in 1734. His family ventured into the Yadkin valley of North Carolina in 1750 when Boone was 15. Four years later, he fought in the French and Indian War. A skilled woodsman, crack shot and tireless wayfarer, Boone later served two terms in the Virginia General Assembly, kept a tavern, led wars against the Shawnee Indians and continually moved around to escape what he called the “too crowded” conditions of 18th century Kentucky.

This driving tour follows the Wilderness Trail to Cumberland Gap as closely as possible. This guide is arranged by stops, beginning at the Long Island of the Holston near the historic Netherland Inn.

Friends along the Wilderness Trail

Sycamore Shoals State Park

Sycamore Shoals State Park in Elizabethton, TN – site of the famous Transylvania Purchase


Wilderness Road State Park

Wilderness Road State Park in Ewing, VA – site of Historic Martin’s Station


Martin’s Station

Historic Martin’s Station – An authentic replica of a Frontier fort located at Wilderness Road State Park in Ewing, VA


Cumberland Gap National Historical Park

Cumberland Gap National Historical Park, KY – the Gateway to Kentucke


The Boone Society

The Boone Society is an association dedicated to studying the Boone Family.


Our friend and DBWTA member, Randell Jones has been working on this interactive map for several months and has offered its use to groups who are working up and down the Boone Historic Corridor to preserve the original pathway that Boone blazed in 1775. We appreciate the opportunity to support Randell’s work and to offer this interactive map for our readers’ use.

Randell is a highly acclaimed author, lecturer, and storyteller from North Carolina. Linking to the map will not only give you a sense of Boone’s movements between the Yadkin Valley of North Carolina to Fort Boonesborough in Kentucky, it will also give you access to extensive information about Randell’s many books dealing with the early frontier in North Carolina, Southwestern Virginia, Tennessee, Kentucky, and beyond as the Westward Movement progressed. We know you will enjoy learning about his many publications, and we appreciate being able to offer our readers access to this excellent interactive map.

Beginning on March 10, Curtis Penix, an avid hiker from Monroe, Michigan plans to walk in the footsteps of his 5X great grandfather, Joshua Penix, who arrived at Fort Boonesborough in 1779. Curtis plans a 16-day hike along Boone Trace, as did his grandfather, beginning at Kingsport, TN on March 10 and terminating at Fort Boonesborough March 26.

He will walk the entire route, carry his own food and sleep under the stars. Others have traveled the general route of the Trace; but, Penix will hike the Trace using the primitive trails as much as possible. The Boone Trace was the first road ever blazed into Kentucky.

Penix says “I thought it would be interesting to travel the road my ancestor had traveled. Even though this road helped to carry 300,000 pioneers into the land we now know as Kentucky, it does not exist today as a singular route. Much of the old path has been paved over as residential streets or 2 lane highway. The portions which followed creeks were abandoned for wider roadways and left to grow over. Much has been tilled under for agriculture. Most of the original Boone Trace has been lost the way an artist would paint over the original painting on a canvas. In order to walk with Joshua, I need to peel back the layers of new paint to reveal the original masterpiece that Boone and his men created.”