The Wilderness Road Opens Kentucky

Daniel Boone escorting settlers through the Cumberland Gap by George Bingham

Daniel Boone escorting settlers through the Cumberland Gap by George Bingham

On March 10, 1775, Daniel Boone and about 30 ax-wielding road cutters (including his brother and son-in-law) set off from the present-day Kingsport, Tennessee traveling north along a portion of the Great Warrior’s Path, heading through Moccasin Gap in the Clinch Mountains. About 20 miles from the Cumberland Gap, Boone and his party rested at Martin’s Station before moving on. On March 24, 1775, Boone’s group was only 15 miles from their final destination of the Kentucky River when they camped for the night. Just before daybreak, a group of Shawnee warriors attacked the sleeping men. Most of the 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.

On March 28, 1775, Judge Richard Henderson followed Boone’s rough trail through the forests and mountains, leaving Kingsport with about 30 horsemen.

At Martin’s Station, some 40-50 additional pioneers joined the group. On their way, they met nearly a hundred refugees fleeing Native American attacks further down the road. Despite the danger, the party continued, and on April 20, 1775, they arrived at what they named Boonesborough in honor of Daniel Boone.


Wilderness Road map

Wilderness Road Map

The Wilderness Road first blazed some 200 miles from Fort Chiswell, Virginia through the Cumberland Gap into central Kentucky, enabled the founding of the first settlements in the Blue Grass State, including Boonesboro, Harrod’s Town, and Benjamin Logan’s. After the outbreak of the Revolutionary War, the rush towards western settlement began, and it would continue throughout the war and beyond. Sometime after it was initially blazed, the path was lengthened, following Native American trails, to reach the Falls of the Ohio River at Louisville, Kentucky. Initially, the Wilderness Road was steep and rough, and could only be traversed on foot or horseback.


Not only was the original trail extremely rough, it was dangerous with attacks from Indians and also outlaws who often hid within the woods just waiting to pounce on weaker pioneers. Animals, too, could often be threatening, such as wolves, panthers, bears, and snakes. Because of these threats, most people traveling along the trail were well armed. Over time, defensive log blockhouses, often called “stations,” were built alongside the road that had portholes in the walls for firing at attackers. Though the Cherokee had negotiated with white settlers for the use of their land, not all were pleased with the land sale. These warriors, along with other tribes, such as the Shawnee and the Chickamauga, with whom no agreements had been made, were resentful of the settlers taking their ancestral hunting lands. The French and Indian War had further stirred up their passions against the white man.

Wilderness Road, Kentucky

Wilderness Road, Kentucky

Despite the adverse conditions, thousands of people used the road. After 1770, a surge of over 400,000 Scots-Irish immigrants arrived in the colonies to escape the poor harvest, high rents and religious intolerance of in their homeland. These immigrants, as well as Germans and other Europeans, kept coming and since most of the lands along the Atlantic Coast were already taken, many pressed westward along the Wilderness Road. Enduring a number of hardships, in the winter of 1778-79, the weather was so cold that the Kentucky River froze to a depth of two feet. Also frozen were many of the settlers livestock and horses and the people were forced to eat their frozen carcasses to survive. In the early 1780s, the Chickamauga, under the leadership of Dragging Canoe, ambushed numerous travelers along the road. In the fall of 1784 alone, they killed more than 100 men, women, and children.

From The Long Island of the Holston River in present-day Kingsport, Tennessee, the Wilderness Road went north through Moccasin Gap of Clinch Mountain, then crossed the Clinch River and made its way over rough terrain, now called the Devils Raceway. The trail then crossed Powell Mountain at Kanes Gap, where it ran southwest through the valley of the Powell River to the Cumberland Gap. Beyond the Cumberland Gap, the road forked, with the southern fork passing over the Cumberland Plateau to Nashville, Tennessee via the Cumberland River. The northern fork split into two parts, with the eastern spur headed into the Bluegrass region of Kentucky to Boonesborough and the western spur running to the Falls of the Ohio River in present-day Louisville. As settlements grew southward, the road stretched all the way to Knoxville, Tennessee, by 1792.

In 1792, Kentucky was admitted to the Union as the 15th state. That very first year, the new Kentucky legislature provided money to upgrade the road and four years later, the improved road was opened for wagon and carriage travel. A postal road also opened in 1792 from Bean Station, Tennessee through Cumberland Gap to Danville, Kentucky. This connection of Kentucky to the East was a great advantage to frontier settlers who considered the postal riders heroes and waited eagerly for the arrival of their mail.

As many as 300,000 settlers traveled along the Wilderness Road from 1775 to 1810. In 1818, when the National Road opened, travelers declined on the Wilderness Road. At about the same time, the first steamboat appeared on the Ohio and Mississippi Rivers. By 1840, use of the Wilderness Road had almost ceased. However, during the Civil War, both the Union Army and the Confederate States Army used the Wilderness Road and fought for control of the Cumberland Gap.

Wilderness Road north of London, Kentucky

Wilderness Road north of London, Kentucky by Kathy Weiser-Alexander.

One segment of the Wilderness Road was among the first roads in the United States to be paved. Later, the old trail would be linked to the famous Dixie Highway that connected Detroit, Michigan to Miami, Florida. This new road brought a new industry, tourism, to the rural areas, filling hotels and restaurants with travelers. Today, many modern highways follow much of its route, Cumberland Gap is a National Park, and portions of the Wilderness Road are included in Wilderness Road State Park in Virginia. Martin’s Station has been reconstructed and can be seen about five miles east of Cumberland Gap in Virginia.


© Kathy Weiser/Legends of America, updated December 2018.

Also See:

Byways & Historic Trails

Cumberland Gap

Daniel Boone

Kentucky Main Page


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