Wilderness Road in the context of "U.S. Route 25E"

The Cumberland Gap is a pass in the eastern United States through the long ridge of the Cumberland Mountains, within the Appalachian Mountains and near the tripoint of Kentucky, Virginia, and Tennessee. At an elevation of 1,631 feet (497 m) above sea level, it is famous in American colonial history for its role as a key passageway through the lower central Appalachians.

Long used by Native American nations, the Cumberland Gap was brought to the attention of settlers in 1750 by Thomas Walker, a Virginia physician and explorer. The path was used by a team of frontiersmen led by Daniel Boone, making it accessible to pioneers who used it to journey into the western frontiers of Kentucky and Tennessee. An important part of the Wilderness Road, it is now part of the Cumberland Gap National Historical Park.

Daniel Boone (November 2 [O.S. October 22], 1734 – September 26, 1820) was an American pioneer and frontiersman whose exploits made him one of the first folk heroes of the United States. He became famous for his exploration and settlement of Kentucky, which was then beyond the western borders of the Thirteen Colonies. In 1775, Boone founded the Wilderness Road through the Cumberland Gap and into Kentucky, in the face of resistance from Native Americans. He founded Boonesborough, one of the first English-speaking settlements west of the Appalachian Mountains. By the end of the 18th century, more than 200,000 people had entered Kentucky by following the route marked by Boone.

He served as a militia officer during the Revolutionary War (1775–1783), which in Kentucky was fought primarily between American settlers and British-allied Indians. In 1778, Boone was captured by the Shawnee and was, according to legend, adopted by the Shawnee Chief and given the name "Sheltowee", or Big Turtle. After months of living with the Shawnee, Boone escaped. He was elected to the first of his three terms in the Virginia General Assembly during the war and fought in the Battle of Blue Licks in 1782, one of the last battles of the American Revolution. He worked as a surveyor and merchant after the war, but went deep into debt as a Kentucky land speculator. He resettled in Missouri in 1799, where he spent most of the last two decades of his life, frustrated with legal problems resulting from his land claims.