Daniel Boone and 35 axmen blazed a trail called the Wilderness Road from Virginia through the Cumberland Gap and into central Kentucky for the Transylvania Company. When the trail opened in 1775 it became the route of 70,000 settlers who came to Kentucky on foot or horseback before the trail was upgraded to wagon road in 1796. 
Historical BackgroundIn 1774 Judge Richard Henderson, a land speculator of North Carolina, hired Daniel Boone to blaze a trail through the Cumberland Gap into Kentucky. The Wilderness Road started at Bristol, Virginia (splitting off the Great Valley Road) and headed west along the Virginia-Tennessee border to the Cumberland Gap, across the nearby Cumberland River, and then went northwest to Boonesborough, Kentucky. Eventually, a western spur of the road would reach Harrodsburg, and then Louisville, Kentucky on the Falls of the Ohio River. In 1780, a group of men including a man by the name of John Kincaid, were hired by the Virginia Colony to make the trail wide enough for pack animals.
The road crossed difficult mountains, rushing rivers, and ran through Indian lands. Indian raids and white robbers both were significant problems, so many people chose to travel the road in large groups. But the risks were worth taking for the rewards of bountiful hunting grounds, rich farmland, and good salt licks. Until the 1794 Shawnee Indian defeat at Fallen Timbers, for hostile Indian reasons, the Wilderness Road was the preferred route to Kentucky and used by 75 percent of settlers. It also served as an important passage for cattle, pigs, and sheep drives into and out of Kentucky to market.
The Kentucky legislature paid for the footpath to be upgraded to a wagon road starting in 1792. The wagon road was finished in 1796.
Earlier peace with Indians along the Ohio River, and the opening of the National Road in 1818 provided an easier, safe, more level route to the Ohio Valley and Kentucky. With the introduction of steamboats at about the same time, traffic on the Wilderness Road declined until it was nearly abandoned in the 1840s. However, it was used by both Union and Confederate armies during the American Civil War.
The Wilderness Road was important to settlers in Virginia and Tennessee as well as Kentucky. Some settlers used the road before it passed the Cumberland Gap to reach extreme southwest Virginia, and northeast Tennessee. Other pioneers waited to split off from the Wilderness Road until they passed over the Cumberland River. Then they followed the north side of the river over the "Kentucky barrens" toward the fertile lands of Middle Tennessee (Nashville) on a trail that came to be called the Kentucky Road.
- Bristol, Washington, Virginia
- Cumberland Gap at the juncture of Virginia, Tennessee and Kentucky
- Boonesborough, Madison, Kentucky
Later west fork:
Settlers and Records
Scots-Irish and Germans were the first to use the Wilderness Road in large numbers. For partial list of settlers who used the Wilderness Road, see:
- Don Chesnut, "Fort Boonesborough Settlers," available online (accessed 3 August 2010), citing H. Thomas Tudor, "Early Settlers of Fort Boonesborough," Bluegrass Roots 5:1-14.
- Ranck, George W. Boonesborough, Its Founding, Pioneer Struggles, Indian Experiences, Transylvania Days, and Revolutionary Annals. Louisville, Ky.: John P. Morton, 1901. FHL 1033675; digital versions at Google Books; Internet Archive.
- Robert Foster Johnson, Wilderness Road Cemeteries in Kentucky, Tennessee and Virginia. Owensboro, Ky.: McDowell Publications, 1981. FHL 973 V3j
- Daniel Boone Wilderness Trail Association photos and historical articles about significant places, events and people along the 1775 Wilderness Trail corridor and the early American frontier. Emphasis on Virginia.
- U.S. Department of the Interior, National Park Service, Cumberland Gap National Historic Park photos, detailed history of the road and culture of pioneers, also, nature and science of the park.
- Wikipedia contributors, "Wilderness Road" in Wikipedia, The Free Encyclopedia at http://en.wikipedia.org/wiki/Wilderness_Road (accessed August 4, 2010).
- William W. Luckett, "Cumberland Gap National Historic Park," Tennessee Historical Quaterly 23 (December 1964). Digitized online at http://www.nps.gov/history/history/online_books/cuga/luckett/index.htm (accessed 3 August 2010).
- East Tennessee Historical Society, First families of Tennessee: a register of early settlers and their present-day descendants (Knoxville, Tenn.: East Tennessee Historical Society, c2000) [FHL 976.8 H2ff], 7.