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Introduction

In 1775, the now-legendary frontiersman Daniel Boone blazed a trail through the Cumberland Gap–a notch in the Appalachian Mountains located near the intersection of Kentucky, Virginia and Tennessee–through the interior of Kentucky and to the Ohio River. Known as the Wilderness Road, the trail would serve as the pathway to the western United States for some 300,000 settlers over the next 35 years. Boone’s pioneering path led to the establishment of the first settlements in Kentucky–including Boonesboro–and to Kentucky’s admission to the Union as the 15th state in 1792.

The earliest origins of the Wilderness Road were the traces, or trails, created by the great herds of buffalo that once roamed the region. Native American tribes such as the Cherokee and Shawnee later used the trails to make attacks on each other. They called the path the Athowominee, variously translated as “Path of the Armed Ones” or “The Great Warrior’s Path.” In 1673, Shawnee warriors captured a young man named Gabriel Arthur. Before his release, Arthur became the first white settler known to have crossed through the Cumberland Gap using part of what would become the Wilderness Road.

In 1750, an expedition led by Dr. Thomas Walker set out from Virginia with the aim of exploring lands further west for potential settlement. Discouraged by the rough terrain in southeastern Kentucky, the group turned back, but Walker’s detailed report of the expedition proved to be an invaluable resource for later expeditions, including Boone’s.

Born in Pennsylvania in 1734, Daniel Boone moved with his family to the North Carolina frontier as a youth. He fought in the French and Indian War, and later served two terms in the Virginia General Assembly. Boone first ventured through the Cumberland Gap on a hunting expedition in 1767. In 1773, he sought to lead his family and several others to settle in Kentucky, but Cherokee Indians attacked the group, and two of the would-be settlers, including Boone’s son James, were killed.

Two years later, a group of wealthy investors spearheaded by Judge Richard Henderson of North Carolina formed the Transylvania Company. Their goal was to colonize the rich lands around the Kentucky River and establish Kentucky as the 14th colony. To that end, they hired Boone, the white man considered to have the most knowledge of the existing trails, to blaze a new trail through the Cumberland Gap. To confront the issue of Native American aggression, Henderson decided to approach the Cherokee directly, and in March 1775 his associates negotiated with the Cherokee to purchase the land between the Cumberland and Kentucky rivers, a total of some 20 million acres, for 10,000 pounds of goods. (Virginia’s colonial governor later nullified the sale.)

On March 10, 1775, Boone and around 30 other ax-wielding road cutters (including his brother and son-in-law) set off from the Long Island of Holston River, a sacred Cherokee treaty site located in present-day Kingsport, Tennessee. From there they traveled north along a portion of the Great Warrior’s Path, heading through Moccasin Gap in the Clinch Mountains. Avoiding Troublesome Creek, which had plagued previous travelers along the route, Boone’s group crossed the Clinch River (near what is now Speers Ferry, Virginia) and followed Stock Creek, crossed Powell Mountain through Kane’s Gap and headed into the Powell River Valley.

About 20 miles from the Cumberland Gap, Boone and his party rested at Martin’s Station, a settlement near what is now Rose Hill, Virginia that had been founded by Joseph Martin in 1769. After a Native American attack, Martin and his fellow settlers had abandoned the region, but they had returned in early 1775 to build a more permanent settlement. Just before reaching their intended settlement site on the Kentucky River in late March, Boone’s group was attacked by some of the Shawnee, who unlike the Cherokee had not ceded their right to Kentucky’s land. Most of Boone’s men were able to escape, though a few were killed or injured. In April, the group arrived on the south side of the Kentucky River, in what is now Madison County, Kentucky.

The opening of the Wilderness Road enabled the founding of the first settlements in Kentucky, including Transylvania Colony–which became Boonesboro–Harrod’s Town and Benjamin Logan’s. After the outbreak of the Revolutionary War that same year, the rush towards western settlement began, and it would continue throughout the war and beyond. As many as 300,000 settlers traveled along the Wilderness Road from 1775 to 1810. In addition to its human traffic, the trail provided a route for farm produce intended for sale in markets closer to the coast, as well as goods and supplies to supply the growing western settlements. In 1792, Kentucky was admitted to the Union as the 15 state.

By 1840, use of the Wilderness Road had declined, as advances in engineering had enabled waterway travel via the Erie Canal and through the rivers of the Ohio Valley. Cumberland Gap later became part of the National Parks System, and portions of the Wilderness Road were included in Wilderness Road State Park.