The Wilderness Road was the principal route used by settlers to reach Kentucky for more than fifty years. In 1775, Daniel Boone blazed a trail for the Transylvania Company from Fort Chiswell in Virginia through the Cumberland Gap into central Kentucky. It was later lengthened, following Native American trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep and rough, and could only be traversed on foot or horseback. Despite the adverse conditions, thousands of people used it. In 1792, the new Kentucky legislature provided money to upgrade the road. In 1796, an improved all-weather road was opened for wagon and carriage travel. The road was abandoned around 1840, although modern highways follow much of its route.
The first European explorers of the southern Appalachian Mountains were Spanish. Hernando de Soto and his troops traversed the region in 1540 and 1541 searching for gold. He was followed by several other Spanish expeditions.
The first recorded English explorations of the mountains were those of Abraham Wood, which began around 1650. Later, Wood sent exploring parties into the mountains. The Batts-Fallam expedition reached the New River Valley in 1671. In 1673, Wood sent Gabriel Arthur and James Needham to the Overhill Cherokee of modern Tennessee. The purpose was to try to make direct contact with the Cherokee for trade, so as to bypass the Ocaneechee "middlemen" traders. The expedition did reach the Overhill Cherokee area, but Needham was killed on the return. Gabriel Arthur was almost killed, but was rescued by being adopted by a Cherokee chief. For his own safety, Arthur was then sent with one of the chief's raiding parties. For about a year, he traveled with the Cherokee, throughout the Appalachians. He was probably the first European to visit modern West Virginia and cross the Cumberland Gap. In 1750, Dr. Thomas Walker, an investor in the Loyal Land Company, with five companions, made a famous exploration through the Cumberland Gap and into eastern Kentucky. The Loyal Land Company settled people in southwest Virginia, but not Kentucky.
In 1774, Richard Henderson, a judge from North Carolina, organized a land speculation company with a number of other prominent North Carolinians called the Transylvania Company. The men hoped to purchase land from the Cherokees on the Kentucky side of the Appalachian Mountains and establish a British proprietary colony. Henderson hired Daniel Boone, an experienced hunter who had explored Kentucky, to blaze a trail through the Cumberland Gap into central Kentucky.
Boone recommended three essentials for a pioneer: “A good gun, a good horse, and a good wife.” He also would need a strong body, a sharp ax and good luck. Another essential was salt. Before 1776, it had to be shipped into the Thirteen Colonies from the West Indies at great expense. It was the only meat preservative available for men on the move and Kentucky had an extra lure with its large salt brine lakes near what is today the community of Boonesborough, Kentucky.. The many "salt licks" of Kentucky are today reflected in the many place names in the state that use the words "lick" or "licking". Starting on March 10, 1775 Boone, along with 35 axmen, cut a trail through the forests and mountains to Kentucky. It was a rough mud trail, hardly more than a path. Although the Transylvania Company had obtained title to Kentucky from the Cherokee and Iroquois, they had not from the Shawnee, who lived and hunted in Kentucky, claimed it, and viewed Boone and other settlers as invaders. On March 24, 1775 Boone and his party were only from their final destination of the Kentucky River when they camped for the night. Just before daybreak a group of Shawnee, slinging tomahawks, attacked the sleeping men. Some of Boone's party were killed and a few were wounded but most were able to escape into the woods. Boone regrouped his men and managed to drive off the hostile Shawnee. The party did, however, lose some of their horses. Here Boone built a temporary open barricade with 6 to high logs
From The Long Island of the Holston River (modern Kingsport, Tennessee), the road went north through Moccasin Gap of Clinch Mountain, then crossed the Clinch River and crossed rough land (called the Devils Raceway) to the North Fork Clinch River. Then it crossed Powell Mountain at Kanes Gap. From there it ran southwest through the valley of the Powell River to the Cumberland Gap.
After passing over the Cumberland Gap the Wilderness 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 went into the Bluegrass region of Kentucky to Boonesborough on the Kentucky River (near Lexington). The western spur ran to the Falls of the Ohio (Louisville). As settlements grew southward, the road stretched all the way to Knoxville, Tennessee, by 1792.
Defensive log blockhouses built alongside the road had portholes in the walls for firing at Native American attackers. They were often called "stations". No one knew exactly when the next attack would happen. The Shawnee came from the north, while the Chickamauaga (Cherokees who rejected the land sale treaty) came from the south. The tribes were resentful of the settlers taking their ancestral hunting lands, and the French and Indian War had further stirred up their passions against the white man.
The Scots-Irish were great fighters. They had lived in Ulster, an English colony in Northern Ireland, for a hundred years before coming to America. They had taken over land previously owned by the Irish and had much experience as fighters in defending their homeland.
There was a great variety of animal life in the wilderness. At night, the pioneers could hear the hoots and screeches of owls, the howls of wolves, and the cries of panthers and wild cats. Sometimes the Native Americans imitated these sounds. Poisonous snakes such as copperheads and rattlesnakes blended into the leaves and undergrowth which were a danger to the pioneers, their horses and cattle.
Judge Richard Henderson had made a treaty with the Cherokee at Sycamore Shoals in 1775, purchasing over 20,000,000 acres (80,000 km²) of land between the Cumberland and Kentucky Rivers. On March 28, 1775, he left Long Island (Kingsport, Tennessee) with about 30 horsemen on grueling trip on the Wilderness Road to Kentucky. At Martin's Station 40 to 50 additional pioneers joined the venture. On their way, they met nearly a hundred refugees fleeing Native American attacks further down the road. Despite the danger, the party kept going toward Kentucky. Since some of the streams were flooded, the pioneers had to swim with their horses. On April 20, they arrived at Boonesborough, a fortified town, named by Judge Henderson in honor of Boone. After 1770, a surge of over 400,000 Scots-Irish immigrants came to this country to escape the poor harvest, high rents and religious intolerance of Ulster. Since the better lands had already been taken, they constantly pressed onward to the western frontier of the foothills of the Carolinas.
Yet the flood of Scots-Irish, German, and others immigrants kept coming. Over 200,000 pioneers came over the Wilderness Road, enduring severe hardships. In the winter of 1778-79, the weather was so cold that the Kentucky River froze to a depth of two feet. The frontier settlements alongside the road struggled to survive. Many of the cattle and hogs froze to death. The settlers had to eat frozen cattle and horses to survive.
Often the Chickamauga, under the leadership of Dragging Canoe, would hide in ambush for weeks between Cumberland Gap and Crab Orchard, a distance of . They would not attack large groups but wait for weaker ones who were not able to defend themselves. More than 100 men, women and children were killed in the fall of 1784 along the Wilderness Road. Many families, even in ice and snow, crossed the creeks and rivers without shoes or stockings; they often had no money and few clothes. They lived off the land by hunting in the woods and by fishing in the streams.
Since they had hardly any money, entire families sometimes walked hundreds of miles after landing in America. They even used cattle as pack animals to carry their heavy loads. Cabins were built and land was cleared of trees and undergrowth so crops could be planted.
Chestnut was the most popular wood since its logs could be used to build cabins and rail fences to protect crops from wild animals. It could easily be split into shingles for roofs to cover cabins and barns. Its bark was used to make medicine and tannic acid for tanning and dyeing. In the fall, its rich nuts were used to fatten razorback hogs for the market and the home. Hemlock was also highly valued for its many uses.
A postal road was opened in 1792 from Bean Station, Tennessee through Cumberland Gap to Danville, Kentucky. This was due largely to the efforts of Governor Isaac Shelby of Kentucky. This connection of Kentucky to the East was a great advantage. Frontier settlers considered the postal riders heroes and waited eagerly for their arrival for news from settlements along the trails as well as getting their mail and newspapers.
Use of the Wilderness Road fell when the National Road was opened in 1818, allowing travel to the Ohio River on level ground from the East. At the same time, the steamboat first appeared on the Ohio and Mississippi Rivers, allowing travel both up and down the rivers. (Hitchcock, 85)
During the American Civil War, both the Union Army and the Confederate States Army used the Road. An early battle (Camp Wildcat), stymied the first attempt by the Confederates to seize control of neutral Kentucky. The Cumberland Gap changed hands four times throughout the war. The southern armies used the road for marches into Virginia. General Ulysses S. Grant came down the road for the Union campaign in Tennessee in 1864. Grant was so taken by the Road that he said, "With two brigades of the Army of the Cumberland I could hold that pass against the army which Napoleon led to Moscow.