The section east of Wears Valley (at 321/73) to Pigeon Forge and beyond is completely unconstructed, and will not occur in the foreseeable future.

Aaron Crowson arrived in Wears Valley from North Carolina in 1792 along with his friend, Peter Percefield.

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.

[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.

[7] 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.

[8] 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.

[9] Sometime after the war, Alfred Line (1831–1897) established a farm at the base of Roundtop Mountain, near the southern half of Wear Cove.

A large oak tree provided shelter for funeral-goers, although cold weather and rain often made apparent the need for a building in which to conduct indoor services.

In 1902, according to local lore, the oak tree was destroyed by lightning, and in response, the residents erected Headrick Chapel on the cemetery's grounds.

The chapel's bell would ring once for every year of the deceased's life, a tradition still observed by the inhabitants of Wears Valley.

In 2005, a group of developers led by Ron Ogle and Jerry Miller sought to build 400 houses on the slopes of Cove Mountain.

This raised concern among many Wears Valley residents over the impact such development might have on Cove Mountain's scenic value.

In 2007, Friends of Wears Valley— a group opposed to the development— unsuccessfully petitioned the Sevier County Regional Planning Commission to block the housing expansion on Cove Mountain.

[11][12] While the 2016 Great Smoky Mountains arson fires mainly affected the nearby towns of Pigeon Forge and Gatlinburg, many cabins did burn down in the northern part of the valley.

After a downed power line ignited the dry foliage in Little Cove Gap, an isolated fire quickly spread, thereby consuming the surrounding structures towards the northern end of Wears Valley.