The Wilderness Road was one of two principal routes used by colonial and early national era settlers to reach Kentucky from the East. Although this road goes through the Cumberland Gap into southern Kentucky and northern Tennessee, the other (more northern route) is sometimes called the "Cumberland Road" because it started in Fort Cumberland in Maryland. Despite Kentucky Senator Henry Clay's advocacy of this route early in the 19th century, the northern route was selected for the National Road, connecting near Washington, Pennsylvania into the Ohio Valley of northern Kentucky and Ohio.
In March 1775, land speculator Judge Richard Henderson established the Transylvania Company and hired frontiersman Daniel Boone to blaze the trail from Fort Chiswell in Virginia through the Cumberland Gap, creating a pathway for westward migration. It was later lengthened, following Indian trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep, rough and narrow. It could be traversed only on foot or horseback. By contrast, wagons could travel along the National Road route (originally the Braddock Road blazed by the competing Ohio Company and George Washington circa 1750), particularly after the improvements.
Despite the adverse conditions, thousands of families used the Wilderness Road. 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 (construction on the National Road after Vandalia, Illinois also stopping owing to the Panic of 1837 and early railroad construction), although modern highways follow much of its route.
Early exploration The Appalachian Mountains form a natural barrier to east–west travel. From New York to Georgia there are only five ways to travel to the west, with only three natural interior breaks allowing animal powered travel without great engineering works: the Gaps of the Allegheny in Pennsylvania (the Kittanning Paths), the Cumberland Narrows in northwestern Maryland (host to Nemacolin's Path), and the Cumberland Gap in the four-state region of North Carolina and Virginia on the east side and through the gap, Tennessee and Kentucky.
While late 19th and 20th-century technologies would later bridge the mountain chain in other places, these all required significant civil engineering works to make a road bed past the barrier range geologist classify as the ridge-and-valley Appalachians. Settlers from Pennsylvania tended to migrate south along the Great Wagon Road through the Great Appalachian Valley and Shenandoah Valley.
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.
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 circumvent the Ocaneechee "middlemen" traders.
The expedition reached the Overhill Cherokee area, but Needham was killed on the return trip. Gabriel Arthur was almost killed, but was rescued and 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.
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 1769, Virginia longhunter and explorer Joseph Martin made the first of several forays into the region. Acting as an agent for Dr. Thomas Walker, to whom Martin was connected through family relationships, Martin began an expedition to Powell's Valley in early 1769 in return for a promised land grant from Walker and the Loyal Land Company. Martin and his men built the earliest westernmost frontier fort at present-day Rose Hill, Virginia, a fort dubbed Martin's Station. Later that year Indians chased off Martin and his men, who returned to Albemarle County. Martin returned six years later to rebuild the fort, and a few months later became an agent for Richard Henderson's Transylvania Company, a land speculation enterprise.A Short History of Martin's Station, historicmartinsstation.com
Henderson, a North Carolina judge, organized the Transylvania Company in 1774 with a number of other prominent North Carolinians. 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.
Daniel Boone
Starting on March 10, 1775, Boone, along with 35 axmen, cut a trail from Long Island in Kingsport, Tennessee through the forests and mountains to Kentucky. It was a rough mud trail, hardly more than a path. The Transylvania Company had obtained title to Kentucky from the Cherokee and Iroquois, and even the Shawnee chief Cornstalk, defeated in Dunmore's War, had promised at the Treaty of Camp Charlotte on October 19, 1774, that his tribe would no longer hunt or claim land south of the Ohio River in Kentucky.
Daniel Boone was from Pennsylvania and had migrated south with his family along this road. From an early age, Boone was one of the longhunters who hunted and trapped among the Native American nations along the western frontiers of Virginia, so-called because of the long time they spent away from home on hunts in the wilderness. Boone would sometimes be gone for months and even years before returning home from his hunting expeditions.
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".
The Shawnee 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 lost some of their horses. Here Boone built a temporary open barricade with 6 to high logs.
By the next year, the Shawnee had been joined by the Chickamauga Cherokee in the Cherokee–American wars with the settlers, which lasted until 1794.
Route
The route of the Wilderness Road made a long loop from Virginia southward to Tennessee and then northward to Kentucky, a distance of .
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).Kincaid, p. 77 As settlements grew southward, the road stretched all the way to Knoxville, Tennessee, by 1792.
Western spur
Due to road realignments in many places modern roads do not always follow the old wilderness trails. marker located on Kentucky Route 490, 7 miles north of London, Kentucky
Skaggs Trace The western spur of the Wilderness road was originally known as Skaggs' Trace, marker located on Kentucky Route 490, 7 miles north of London, Kentucky named after the longhunter Henry Skaggs. The trace began just outside Hazel Patch, in present-day Laurel County, a marker is located on Kentucky Route 490, 7 miles north of London, Kentucky and continued to Crab Orchard.
Logan's Trace In 1775, Benjamin Logan's party, that included John Floyd, split with Daniel Boone's party and turned westward on Skaggs Trace. The trail went through the Crab Orchard approximately 10 miles where a Blockhouse was built to protect settlers in the area and named Logan's Fort. From there the trail went to the area that became Danville (1783) originally named Crow's Station in 1774, what would become Springfield (1793), a marker is located on Kentucky Route 490, 7 miles north of London, Kentucky Harrodsburg referred to as Harrod's Town or Oldtown and founded by James Harrod on June 16, 1774, abandoned and resettled in 1775, Bardstown (settled in 1780), Shepherdsville (founded as Bullitt's Lick in 1773), and the Falls of the Ohio.
Robert Emmett McDowell (1914–1975), Kentucky historian and Filson Historical Society member since 1956, claims there are errors in Filson's map. The map shows the trail leaving Louisville through Sullivan's Old Station, Kuvkendahl's Mill, the Fishpools to Bullitt's Lick, then through Bardstown to Danville. McDowell claims that originally the trail went through Harrodsburg not Danville, and Sullivan's Old Station and Kuykendahl's Mill were not on the main road but high water alternate paths. Further claims were made that the Wilderness Trail was improved after General George Rogers Clark landed at the Falls of the Ohio which would facilitate the movement of troops and supplies as well as settlers. a marker is located on Kentucky Route 490, 7 miles north of London, Kentucky
In 1784, Filson, also an historian, wrote The Discovery, Settlement and present State of Kentucke and an Essay towards the Topography, and Natural History of that important Country. Reuben Thomas Durrett indicates there are inaccuracies as well.
Dangers
Because of the threat of Native American attacks, the road was so dangerous that most pioneers traveled well armed. Robbers and criminals also could be found on the road, ready to pounce on weaker pioneers.Kincaid, p. 351 Although the Transylvania Company had purchased the region from the Cherokee, and the Iroquois had ceded it at the Treaty of Fort Stanwix, other tribes, such as the Shawnee, still claimed it and lived there.
Often entire communities and church congregations would move together over the road to new settlements. Hundreds of pioneers were killed by Indian attacks.Kincaid, p. 175
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 Chickamauga (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.Kincaid, p. 116