The earliest origins of the Wilderness Road were the traces, or trails, created by the great herds of buffalo that once roamed the region. These trails were later followed by Native American tribes of the area, such as the Cherokee and Shawnee. These first peoples called it the path the Athowominee, which was translated as the “Path of the Armed Ones” or “The Great Warrior’s Path.”
The first recorded English exploration of the Appalachian Mountains was by explorer and fur trader, Abraham Wood, which began around 1650. Later, Wood sent more exploring parties into the mountains and in 1671, the Batts-Fallam expedition reached the Appalachian divide and found the Indian trail known as the Great Warrior’s Path.
Two years later, in 1673, Wood sent James Needham and his assistant, Gabriel Arthur, to the Cherokee capital at Chota, Tennessee. The purpose was to try to make direct contact with the Cherokee for trade, so as to bypass the Ocaneechee “middlemen” traders.
Needham went back to Virginia to procure trade goods, leaving Gabriel Arthur behind to learn the Cherokee language. On the way, Needham got into an argument with his guide, “Indian John,” and was killed by him. In the meantime, Arthur traveled with the Cherokee, throughout the Appalachians. He was probably the first European to visit modern West Virginia and cross the Cumberland Gap. Arthur was later captured by the Shawnee in 1673, but, was released in hopes of promoting trade with the English.
In 1681, Colonel Cadwallader Jones established trade with Indians beyond the Blue Ridge Mountains even though such contact was discouraged by the Crown of England. Small excursions into eastern Kentucky and trading with the Indians continued for the next several decades; but, it wouldn’t be until 1750, that strides were made for real westward expansion.
In 1750, Dr. Thomas Walker, a surveyor, and investor in the Loyal Land Company led a scouting expedition into the area and discovered the Cumberland Gap, which crossed the mountain barrier into present-day southeastern Kentucky. Walker, along with five companions, set out from Albemarle County, Virginia, with the aim of exploring lands further west for potential settlement. The Loyal Land Co., which sponsored the expedition, was seeking an 800,000-acre land grant in the region. After discovering the gap, which Walker originally named “Cave Gap”, the group followed the “Warriors’ Path” for about ten miles northwest to the Cumberland River, which he also discovered and named. Near the river, the party built a log cabin, one of the first in Kentucky. After spending two months vainly exploring the hills of eastern Kentucky in search of the storied Bluegrass region of central Kentucky, the party crossed the mountains north of Cumberland Gap and returned home. In the short-term, the Loyal Land Company settled people in southwest Virginia, but not Kentucky.
Further exploration of the area was sharply curtailed because the wars with the Indians and the French kept the frontier closed. Relative peace came in 1761 with the pacification of the Cherokee following the bloody uprising during which Fort Loudoun was taken and it’s occupants massacred. That same year, long hunter Elisha Wallen led a group of hunters into Southwest Virginia and they roamed the area for eighteen months. News of Wallen’s adventure spread and soon, other wandering long hunters followed. In 1767 Daniel Boone came from the Yadkin Valley of North Carolina and got as far as the Big Sandy River before turning back.
In 1769, Dr. Thomas Walker requested that explorer, Joseph Martin, make additional forays into the region. Martin first began an expedition to Powell’s Valley in return for a promised 21,000-acre land grant from the Loyal Land Company. Martin and his men built the earliest westernmost frontier fort at present-day Rose Hill, Virginia, which was called Martin’s Station.
That same year, Daniel Boone, John Finley, with whom, had served in Braddock’s army during the French & Indian War, and four others made their way along the Wilderness Trail to Kentucky. Just before reaching Cumberland Gap, they came upon Joseph Martin and some 20 other men, building the settlement and fort called Martin’s Station. Boone moved on and would spend two years hunting and trapping in eastern Kentucky. However, Martin and his men would be chased off the land where they had settled by Indians. Six years later, Joseph Martin returned to the area and rebuilt the fort.
In 1773, Daniel Boone sought to lead his family and several others to settle in Kentucky, however, Cherokee Indians attacked the group, and two of the would-be settlers, including Boone’s son James, was killed.
In 1774, Judge Richard Henderson and other prominent North Carolinians established the Transylvania Company, a land speculation company. The men hoped 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 then negotiated with the tribesmen, purchasing over 20,000,000 acres of land between the Cumberland and Kentucky Rivers, for a price of 10,000 pounds worth of trade goods. The purchase included most of eastern Kentucky and a portion of middle Tennessee. Henderson and the Transylvania Company then hired Daniel Boone to blaze a trail through the Cumberland Gap into central Kentucky.