In 1785, when James Winchester first set foot in what would become Sumner County, Tennessee, there was no Cragfont and perhaps there wasn’t even a dream of it...yet.
James and his brother George came to the Western frontier in search of their fortunes. Grizzled and war weary from seven years of service in the American Revolution, the two brothers sought a different kind of adventure. One they surely hoped would reap financial rewards. They began by building a fort on the land now occupied by Cragfont. James liked to call it Fort Tuckahoe, but his fellow frontiersmen and women preferred Winchester’s Fort. Here a few families lived together for protection against raids by Native Americans. James and his brother built a mill, sawmill, distillery and a cabin.
Violence between Native Americans and white settlers was a regular occurrence on the Tennessee frontier as both groups fought to protect their own interests. White settlers believed they had authority to take possession of lands in the west. In the process, indigenous sovereignty was subversively, and often blatantly, disregarded by illegal white settlement. James and George both actively participated in the illegal settlement of native lands. Both were also militia officers that engaged in warfare with native people. Tensions were further exacerbated by ever-increasing racism and anti-indian sentiment. These conflicts were numerous and there were many casualties, both white and Native. In fact, many of these skirmishes took place right here, when Fort Tuckahoe and Croft Mill were attacked multiple times over the years. Several occupants were killed. George was one of the last casualties of this long war. He died in 1794. Colonel William Martin, a contemporary of James and George Winchester, said of George, “he was a superior man in every way to the General.”