Wears Valley is named after Samuel Wear (1753–1817), a Revolutionary War veteran who erected a fort near the entrance to the valley in what is now Pigeon Forge. The original name of the valley was "Crowson Cove," after its first settler, Aaron Crowson (1774–1849). While no one is sure why its name changed, the valley was using its current name by 1900.
Crowson arrived in Wears Valley from North Carolina in 1792 along with his friend, Peter Percefield. This was during a period of elevated strife between the Cherokee and the fast-encroaching Euro-American settlers. Wear's Fort was attacked in 1793, with Wear leading a punitive march against the Cherokee village of Tallassee shortly thereafter. In May 1794, Percefield was killed in a Cherokee attack. Crowson rode to Wear's Fort to get help, but the Cherokee had fled by the time he returned. Several settlers marched onward to Great Tellico to the west, where they killed four Cherokee while they slept. Percefield was buried on a hill in the eastern half of Wear Cove, in what is now Crowson Cemetery. Later that year, Crowson received a land grant for this plot of land.
Along with Crowson, other early settlers in Wears Valley included a Revolutionary War veteran named William Headrick (1744–1839), who arrived in 1821, and John Ogle (1788–1841), a War of 1812 veteran and son of the first settlers in Gatlinburg. Another War of 1812 veteran, Peter Brickey (1769–1856), arrived in 1808. Brickey operated a large farm and distillery in the valley until his death in 1856. The log house he built shortly after his arrival still stands in Smith Hollow (between Wears Valley and Townsend) and is listed on the National Register of Historic Places.
Like many other farms in Wears Valley, the Brickey farm was ravaged by the U.S. Civil War. Isaac Trotter, who operated the iron forge at Pigeon Forge reported a Cherokee raid in Wear Cove in 1864.[6] Earlier in the war, a Union army passed through the valley en route to dislodge the troops of Will Thomas who were entrenched in Gatlinburg. William C. Pickens, a resident of Wears Valley, was one of the so-called bridge-burners, a band of pro-Union guerillas who attempted to destroy several railroad bridges across East Tennessee in November 1861. Pickens led the failed attack on the Strawberry Plains bridge, and was badly wounded in the attack. Pro-Union newspaper editor William "Parson" Brownlow, wanted by Confederate authorities for complicity in the bridge burnings, hid out in Wears Valley at the home of Valentine Mattox in November 1861.
Sometime after the war, Alfred Line (1831–1897) established a farm at the base of Roundtop Mountain, near the southern half of Wear Cove. Line Spring, a clear mountain spring which flows down from the slopes of Roundtop, gave its name to a small recreational area that developed in this part of the cove. In the 1880s and 1890s, mineral-rich mountain springs were thought to have health-restoring qualities, and provided an early form of tourism for the mountain regions. In 1910, D.B. Lawson, the son of a circuit rider who had purchased the Line farm, constructed the Line Spring Hotel. The hotel boosted the valley's economy by providing a market for local farmers.