Wilderness Road

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 (more northern route) 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.

In 1775, Daniel Boone blazed a trail for the Transylvania Company from Fort Chiswell in Virginia through the Cumberland Gap. It was later lengthened, following Indian trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep, rough and narrow. It could be traversed only on foot or horseback. By contrast, wagons could travel along the National Road route (originally the Braddock Road blazed by the competing Ohio Company and George Washington circa 1750), particularly after the improvements.

Despite the adverse conditions, thousands of families used the Wilderness Road. In 1792, the new Kentucky legislature provided money to upgrade the road. In 1796, an improved all-weather road was opened for wagon and carriage travel. The road was abandoned around 1840 (construction on the National Road after Vandalia, Illinois also stopping owing to the Panic of 1837 and early railroad construction), although modern highways follow much of its route.

The Appalachian Mountains form a natural barrier to east–west travel. From New York to Georgia there are only five ways to travel to the west, with only three natural interior breaks allowing animal powered travel without great engineering works: the Gaps of the Allegheny, the Kittanning Paths in Pennsylvania, the Cumberland Narrows in northwestern Maryland (host to Nemacolin's Path), and the Cumberland Gap in the four-state region of North Carolina and Virginia on the east side and through the gap, Tennessee and Kentucky.

While late 19th and 20th-century technologies would later bridge the mountain chain in other places, these all required significant civil engineering works to make a road bed past the barrier range geologist classify as the ridge-and-valley Appalachians. Settlers from Pennsylvania tended to migrate south along the Great Wagon Road through the Great Appalachian Valley and Shenandoah Valley.^{[citation needed]}

The first European explorers of the southern Appalachian Mountains were Spanish. Hernando de Soto and his troops traversed the region in 1540 and 1541 searching for gold.

The first recorded English explorations of the mountains were those of Abraham Wood, which began around 1650. Later, Wood sent exploring parties into the mountains. The Batts-Fallam expedition reached the New River Valley in 1671. In 1673, Wood sent Gabriel Arthur and James Needham to the Overhill Cherokee of modern Tennessee. The purpose was to try to make direct contact with the Cherokee for trade, so as to circumvent the Ocaneechee "middlemen" traders.

The expedition reached the Overhill Cherokee area, but Needham was killed on the return trip. Gabriel Arthur was almost killed, but was rescued and adopted by a Cherokee chief. For his own safety, Arthur was then sent with one of the chief's raiding parties. For about a year, he traveled with the Cherokee throughout the Appalachians. He was probably the first European to visit modern West Virginia.