Daniel Boone 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 blazed the Wilderness Road through the Cumberland Gap and into Kentucky, in the face of resistance from American Indians, for whom the area was a traditional hunting ground. 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.

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 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.