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[[Image:Cumberland Gap and Wilderness Road.jpg|center|Cumberland Gap and Wilderness Road.jpg]]The Cumberland Gap is a natural break in the Appalachian Mountain range (through the Allegheny Mountains), first used by hunting and war parties of rival Indian tribes north of the Ohio River and south of the mountains. In 1750, Dr. Thomas Walker discovered this gap, first called Cave Gap but later named Cumberland Gap. During that same year, Christopher Gist crossed the whole of Kentucky to the Miami River. In 1769 Daniel Boone reached the Cumberland Gap and passed into the Blue Grass hunting ground of both the northern and southern Indian tribes. Reports of this fertile region attracted land-hungry pioneers.
<br>Although illegal under the terms of the Proclamation of 1763, Judge Richard Henderson of North Carolina in 1775 organized the Transylvania Company to buy land from the Indians to sell to white settlers. Next, the Transylvania Company sent Daniel Boone and thirty woodsmen to mark off a trail from the eastern settlements through the Cumberland Gap and down the Kentucky River to the Ohio, a route which later took the name Wilderness Road. Boone established Boonesborough, a small fort on the Kentucky River, near the present city of Lexington.
Some historians suggest that the origin of the Wilderness Road was at Fort Chiswell on the Great Valley Road where roads converged from Philadelphia and Richmond. Others claim the Wilderness Road actually began at Sapling Grove (now Bristol, Virginia) which lay at the extreme southern end of the Great Valley Road because it was at that point that the road narrowed, forcing travelers to abandon their wagons. The Wilderness Road moved through the Allegheny Mountains at Cumberland Gap, at what is now the junction of the state boundaries of Kentucky, Tennessee, and Virginia. Heading northwest, it splits at Hazel Patch, with one route to Boonesborough, the other to Frankfort.
In the early years, the Wilderness Road was simply a crude trail. Only pack teams could cross the mountains. Pioneers coming from Pennsylvania, Maryland, Virginia, and the Carolinas before 1796 found it necessary to unload their Conestoga wagons at Sapling Grove and pack their belongings on horses. They lashed huge baskets and bundles of clothing, bed furnishings and household articles upon packhorses. Children perched on top, or rode in front and behind their mothers. The older boys and men who did not have mounts had to trudge along on foot. A caravan of pack horses and people on foot sometimes stretched out as far as three miles along the trail. Professional packhorse men made it a business to hire out to settlers or merchants for transporting supplies through the wilderness. They objected to road improvements, saying it would drive them out of business. Nevertheless, changes came about and swarms of people crossed through the Gap into Kentucky and beyond.
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