The Wilderness Road was a major route of travel for American settlers heading west for several decades in the late 18th and early 19th Centuries.

The Wilderness Road began at the (inland) settlement of Roanoke in Virginia and stretched through the famous Cumberland Gap through the Appalachian Mountains into what is now Lexington, Ky.

One of only three passes through the imposing Appalachian chain, the Cumberland Gap was the product of natural forces during a period of centuries and was used by animals and Native Americans, Cherokee and Shawnee among them, long before English settlers arrived. Native Americans referred to the pathway through the mountains as Athowominee, one English translation of which is "Path of the Armed Ones." As more and more people from England settled in to the North American colonies, they sought more and more opportunities to seek out new lands; in most cases, this meant heading west.

Leading the first known explorers from what is now the United States through the Cumberland Gap was Dr. Thomas Walker a physician who had a knack for finding his way in the wild. Walker had heard stories of the Gap from Native Americans who lived nearby. Walker's party went through the Gap in 1750.

The Cumberland Gap was not much more than a footpath when Walker's party went through it. The V-shaped Gap was certainly not fit for travel by goods-laden wagons.

In 1775, the famed explorer Daniel Boone, who had first gone through the area six years earlier, led a party of woodsmen through the Gap, blazing what came to be called Boone's Road. They were in the employ of the Transylvania Company. Boone and his party of 30 ax-wielding trailblazers left what is now Kingsport, Tenn., on March 10. They went through Moccasin Gap in the Clinch Mountains, crossed the Clinch River and Powell Mountain, and stopped at Martin's Station, a settlement that Joseph Martin had founded in 1769 but had abandoned after an attack by Native Americans. Boone and his party were set on by hostile Native Americans as well, and some of Boone's men died in the attack. The survivors pressed on, navigated the Cumberland Gap, and then arrived in what is now Kentucky, a few weeks after they set out. Boone and his men established a settlement, later named Boonesborough.