Henry Earnest, born in 1732, was already farming the Nolichucky bottomlands when the American Revolution broke out. The family supported the Patriot cause: Earnest's son Felix fought at the Battle of Kings Mountain in 1780, a decisive Patriot victory in the Carolina backcountry. When Greene County was created out of Washington County, North Carolina in 1783, Henry Earnest served as its first tax assessor. His son Henry Earnest Jr. represented the county in the Tennessee state senate from 1811 to 1813 and became a founding board member of Tusculum College when it was chartered in 1818. Tusculum is the oldest college in Tennessee. The Earnests' civic involvement in the founding of nearly every local institution — county government, college, church — meant their farms were never just farms. They were the physical center of how a community organized itself out of frontier into something more settled.

The Earnest Fort House was finished in 1782 or 1783. Its first-story walls are limestone block, thick enough to repel small-arms fire; the upper two stories are logs joined with V-notches. It was added to the National Register in 1978 in its own listing, before being incorporated into the district. The Henry and Peter Earnest House began as a rear wing built by Henry around 1800. In 1820, Peter Earnest added a Federal-style brick front facade, creating the I-house silhouette that Southern farmsteads kept building for the next century. A separate two-story brick smokehouse went up the same year, later repurposed for milk storage when the family experimented with dairying. A Colonial Revival portico was added in the 1920s. The Earnest Bridge Substructure — a stone pier rising from the river just west of the modern TN-351 crossing — was built in 1903 using stones recycled from the 1869 toll bridge that Peter Earnest had originally established in the 1850s to connect the farms to the East Tennessee and Georgia Railroad. Helene's flood destroyed the abutment in September 2024.

When Peter Earnest expanded the family house in 1820, he added a smokehouse and slave quarters to the rear. The National Register documentation names this directly. Enslaved people farmed this land, built these outbuildings, and kept this household running for the decades before the Civil War. East Tennessee was Unionist territory — Greene Countians voted 2,691 to 744 against secession in June 1861 — but Unionism and slaveholding were not mutually exclusive in this part of the South. Some of the most prosperous Unionist families owned enslaved workers, including the Earnests. Acknowledging this is part of reading the property honestly. The brick that Peter Earnest had laid was almost certainly fired and stacked by enslaved hands. The smokehouse where bacon was cured to feed everyone on the farm was operated by people who were not free.

After Emancipation and the war, the Earnest farms survived mostly intact, though the local economy was wrecked. The toll bridge was rebuilt in 1869 and again in 1903. The Broyles family bought the Henry Earnest Jr. properties in 1903 and, in the 1940s, tried to convert the operation to dairy farming to take advantage of a Pet Milk condensing plant in Greeneville. The dairy venture failed — small mountain farms could not match the consolidation pressures of mid-century agriculture — and the Broyles, Elmwood, and Crum farms turned back to tobacco, which is still their chief crop. The Crum Farm, developed in the 1920s, includes a board-and-batten chicken coop whose design may have been based on extension publications from the University of Tennessee. The Jim Earnest Farmstead, a separate property inherited through Felix Earnest's line, centers on a three-story 1880 Folk Victorian house with an Italianate-influenced front bay. These are not preserved museums. They are still farms, still working, still doing what families have done at this river bend for 250 years — though Helene's flooding in 2024 left scars that the community is still measuring.