Prior to the establishment of the county the area had been used as a hunting preserve by Native Americans, and white encroachment into the area violated existing treaties with the Indians. In the Alpine community the Cherokee inhabitants were referred to as “Nettle Carrier” Indians and were friendly with white explorers. In 1763 a party of Long Hunters explored the area and camped for a time at the current location of Waterloo on Spring Creek and later along the Roaring River. A number of the Long Hunters chose to remain, to the chagrin of the Cherokees. In 1769 one of those frontiersmen, Robert Crockett, was ambushed in the Oak Hill area and killed; he is purported to be the first white man to die in Middle Tennessee.
In 1797 the idealistic and peripatetic Dr. Moses Fisk moved into the county. A recent graduate of Harvard who was licensed to practice law, Fisk wanted to tame the wilderness and pursue the American dream. He established a settlement at Hilham, which is one of the oldest communities in the county. Fisk, thinking Hilham was the geographical center of the entire globe, started four roads radiating out of Hilham in the four major directions of the compass, convinced that all roads would lead to his new Rome in the wilderness. In an era of male dominance, Fisk established a Female Academy–one of the first such schools in the entire South–at Hilham in 1806.
After the American Revolution many veterans received land grants from the federal government and moved into the region. In 1799 Colonel Stephen Copland and his son “Big Jo” left Kingston and established a settlement near Monroe. Copland worked out a hospitable arrangement with the Cherokee chief Nettle Carrier and was allowed to establish a home site. His success encouraged further settlement.
Pickett, Fentress, Putnam, Jackson, and Clay counties.