Hickey’s Road, first laid off by court order in 1749, followed this general path. Named after John Hickey, a merchant who operated a store at its western limits and peddled his wares along its length, the road stretched more than 100 miles from Halifax County, past Mt. Airy and Chalk Level in Pittsylvania, and into Chatham before proceeding westward to the foothills of the Blue Ridge Mountains. A major thoroughfare home to many stores and ordinaries, the road played a major role in European settlement in Southside Virginia in the 18th and 19th centuries.