South Hill was formerly located on the old Buckhorn Road near the Meherrin River. It was the site of the first chartered school in Mecklenburg County in 1814. When the founder/teacher/minister/postmaster died in 1857, many from the community relocated 3 miles east to the Boydton-Petersburg Plank Toll Road. In 1888, W. W. Buck Harris, a local wheelwright and landowner at Piney Pond and Plank Road, died. At auction, 55 acres of his property were purchased, platted, and parceled for sale by A. E. Batemen and Charles Peck to establish a new South Hill community, which surrounded the Atlantic-Danville Railroad depot. Following this, South Hill became known as the town of highways. With each new highway came significant changes for the town and county.