The Wilderness Road Opens Kentucky
The story of Kentucky’s settlement is inextricably linked to a rugged, winding pathway carved through the formidable Appalachian Mountains: The Wilderness Road. This crucial artery, the primary route for westward expansion for over half a century, facilitated the movement of settlers from the established East Coast into the fertile lands of Kentucky. Its origins trace back to the natural world, shaped by the migrations of buffalo and later utilized by Native American tribes, before being forged into a usable passage by frontiersmen like the legendary Daniel Boone.
The genesis of the Wilderness Road lies in the ancient trails etched into the landscape by massive herds of buffalo. These powerful creatures instinctively sought the easiest routes through the mountainous terrain, creating pathways that followed natural contours and water sources. Following in their wake came the Native American tribes, including the Cherokee and Shawnee, who adopted and expanded these trails for hunting, trade, and warfare. They knew it as the Athowominee, a name imbued with meaning, translating to "Path of the Armed Ones" or "The Great Warrior’s Path," a testament to its strategic importance and the conflicts that often surrounded it.
The exploration of the Appalachian Mountains by English colonists began in earnest around 1650 with Abraham Wood, an explorer and fur trader. Recognizing the potential for trade and expansion, Wood dispatched numerous expeditions into the uncharted territories. A pivotal moment arrived in 1671 when the Batts-Fallam expedition successfully traversed the Appalachian divide, encountering and documenting the well-worn Indian trail known as the Great Warrior’s Path. This marked a significant step towards understanding and ultimately utilizing this natural corridor.
Driven by the desire to establish direct trade relations with the Cherokee and circumvent the Ocaneechee traders who acted as middlemen, Abraham Wood sent James Needham and his assistant, Gabriel Arthur, to the Cherokee capital of Chota, Tennessee, in 1673. This mission was fraught with peril. Needham’s journey back to Virginia to acquire trade goods ended tragically when he was killed by his guide, "Indian John." Arthur, however, remained with the Cherokee, immersing himself in their culture and language.
Arthur’s time with the Cherokee led him on journeys throughout the Appalachian region. He is believed to be the first European to set foot in present-day West Virginia and, more importantly, to cross the Cumberland Gap, a natural break in the mountain chain that would become the linchpin of the Wilderness Road. Though later captured by the Shawnee in 1673, he was eventually released to promote trade between the tribe and the English.
Despite the Crown of England’s discouragement of contact with Native Americans beyond the Blue Ridge Mountains, Colonel Cadwallader Jones established trade with them in 1681. Small-scale excursions into eastern Kentucky and trade with indigenous populations continued for several decades. However, it wasn’t until 1750 that significant strides towards westward expansion began to take shape.
Dr. Thomas Walker, a surveyor and investor in the Loyal Land Company, spearheaded a scouting expedition in 1750 that would prove instrumental in opening Kentucky. His discovery of the Cumberland Gap, initially named "Cave Gap," provided a crucial passage through the imposing mountain barrier into what is now southeastern Kentucky. Walker, accompanied by five companions, embarked from Albemarle County, Virginia, with the explicit purpose of exploring lands further west for potential settlement. The Loyal Land Company, the expedition’s sponsor, had its sights set on securing an 800,000-acre land grant in the region.
Following their discovery of the Cumberland Gap, Walker and his party ventured about ten miles northwest, following the "Warriors’ Path" to the Cumberland River, which he also named. Near the river, they erected a log cabin, one of the earliest structures built by Europeans in Kentucky. For two months, the expedition explored the hills of eastern Kentucky, hoping to find the legendary Bluegrass region of central Kentucky. Ultimately unsuccessful in this endeavor, the party crossed the mountains north of Cumberland Gap and returned home. Although the Loyal Land Company didn’t immediately establish settlements in Kentucky, it did settle people in southwest Virginia.
The outbreak of wars with Native Americans and the French severely hampered further exploration of the area, effectively closing the frontier. A period of relative peace emerged in 1761 following the pacification of the Cherokee, which followed a bloody uprising during which Fort Loudoun was captured and its occupants massacred. In that same year, the long hunter Elisha Wallen led a group of hunters into Southwest Virginia, roaming the area for 18 months. News of Wallen’s adventure spread, and other long hunters soon followed. In 1767, Daniel Boone arrived from the Yadkin Valley of North Carolina, reaching the Big Sandy River before turning back.
In 1769, Dr. Thomas Walker commissioned explorer Joseph Martin to make further forays into the region. Martin launched an expedition to Powell’s Valley in exchange for a promised 21,000-acre land grant from the Loyal Land Company. Martin and his men constructed Martin’s Station, the westernmost frontier fort of its time, near present-day Rose Hill, Virginia.
That same year, Daniel Boone, accompanied by John Finley, with whom he had served in Braddock’s army during the French & Indian War, and four others, traveled along the Wilderness Road to Kentucky. Just before reaching Cumberland Gap, they encountered Joseph Martin and about 20 men building Martin’s Station. Boone continued onward, spending two years hunting and trapping in eastern Kentucky. However, Martin and his men were soon driven off the land by Native Americans. Joseph Martin returned to the area six years later and rebuilt the fort.
In 1773, Daniel Boone attempted to lead his family and several others to settle in Kentucky. However, the group was attacked by Cherokee Indians, resulting in the deaths of two settlers, including Boone’s son James.
Judge Richard Henderson and other prominent North Carolinians established the Transylvania land speculation company in 1774. Their aim was to purchase land from the Cherokee on the Kentucky side of the Appalachian Mountains and establish a 14th colony. In February 1775, Henderson arrived at Sycamore Shoals, the ancient treaty grounds of the Cherokee. He negotiated with the tribesmen, purchasing over 20,000,000 acres of land between the Cumberland and Kentucky Rivers for 10,000 pounds of trade goods. The purchase encompassed most of eastern Kentucky and a portion of middle Tennessee. Henderson and the Transylvania Company hired Daniel Boone to blaze a trail through the Cumberland Gap into central Kentucky.
On March 10, 1775, Daniel Boone, along with approximately 30 ax-wielding road cutters, including his brother and son-in-law, departed from present-day Kingsport, Tennessee. They traveled 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 continuing their journey. On March 24, 1775, Boone’s group, now only 15 miles from their final destination on the Kentucky River, camped for the night. Just before daybreak, a group of Shawnee warriors attacked the sleeping men. While most escaped, some were killed or injured. In April, the group finally arrived on the south side of the Kentucky River in 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.
Some 40-50 additional pioneers joined the group at Martin’s Station. En route, they encountered nearly a hundred refugees fleeing Native American attacks further down the road. Undeterred by the danger, the party continued, arriving on April 20, 1775, at what they named Boonesborough in honor of Daniel Boone.
The Wilderness Road, initially stretching some 200 miles from Fort Chiswell, Virginia, through the Cumberland Gap into central Kentucky, paved the way for the founding of the first settlements in the Blue Grass State, including Boonesboro, Harrod’s Town, and Benjamin Logan’s. With the outbreak of the Revolutionary War, the surge toward Western settlement accelerated, continuing throughout the war and beyond. Over time, the path was extended, following Native American trails to reach the Falls of the Ohio River at Louisville, Kentucky. Initially, the Wilderness Road was steep, rough, and suitable only for foot or horseback travel.
The original trail was not only extremely rough but also fraught with danger. Attacks from Native Americans and outlaws, who often lurked within the woods, were a constant threat to the vulnerable pioneers. Animals such as wolves, panthers, bears, and snakes added to the peril. As a result, most travelers along the Wilderness Road were well-armed. Over time, defensive log blockhouses, often called "stations," were constructed along the road, featuring 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 and other tribes, such as the Shawnee and the Chickamauga, with whom no agreements had been made, resented the settlers taking their ancestral hunting lands. The French and Indian War had further fueled their animosity towards the white man.
Despite the adverse conditions, thousands of people used the road. After 1770, over 400,000 Scots-Irish immigrants arrived in the colonies, seeking refuge from their homeland’s poor harvests, high rents, and religious intolerance. These immigrants, along with Germans and other Europeans, continued to arrive, and with most of the lands along the Atlantic Coast already claimed, many pressed westward along the Wilderness Road. Enduring severe hardships, the winter of 1778-79 brought weather so cold that the Kentucky River froze to a depth of two feet. Many settlers’ livestock and horses also froze, forcing the people to consume their frozen carcasses for survival. 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 the 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. The southern fork passed over the Cumberland Plateau to Nashville, Tennessee, via the Cumberland River. The northern fork split into two parts: the eastern spur headed into the Bluegrass region of Kentucky to Boonesborough, and the western spur ran to the Falls of the Ohio River in present-day Louisville. As settlements grew southward, the road stretched to Knoxville, Tennessee, by 1792.
In 1792, Kentucky was admitted to the Union as the 15th state. That same year, the new Kentucky legislature allocated funds to upgrade the road. Four years later, the improved road was opened for wagon and carriage travel. A postal road 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.
An estimated 300,000 settlers traveled the Wilderness Road between 1775 and 1810. With the opening of the National Road in 1818, traffic on the Wilderness Road declined. Around the same time, the first steamboat appeared on the Ohio and Mississippi Rivers. By 1840, the use of the Wilderness Road had nearly ceased. However, during the Civil War, both the Union and Confederate armies utilized the Wilderness Road and fought for control of the Cumberland Gap.
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, connecting Detroit, Michigan, to Miami, Florida. This new road brought industry and tourism to 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.