Round Hill was incorporated on February 5, 1900. From 1874 to 1900, the settlement had been the terminus of a Washington and Ohio rail line that ultimately became the Washington and Old Dominion Railroad. The railway allowed agricultural products to be brought into Washington, D.C., and allowed the residents of the District to escape to the surrounding countryside for holidays. Many of the town's older residences were originally boarding houses, inns, and taverns where people would go upon arrival. The town was considered a convenient destination as it lies close to the Shenandoah River (7 miles / 11.3 km distant), the Shenandoah National Park (30 miles / 48 km), the Appalachian Trail (4 miles / 6.4 km), Harpers Ferry (15 miles / 24 km), the Chesapeake and Ohio Canal Tow Path (used currently as a bike trail) (12 miles / 19 km), and the paved Washington & Old Dominion Railroad Trail (3 miles / 4.8 km).