Cragfont is located on the original road from Knoxville and the East coast, The house stood as a grand and prominent landmark for those making their way west. Originally hunting grounds for local native American peoples, 33 year old James and his brother George arrived in 1785 and quickly established a fort on land given for their service in the American Revolution. By 1802, Winchester built his home Cragfont, occupied by his growing family and the enslaved community until 1863. Following the Civil War, the remaining family members sold the home and in 1957, it became a state historic site.