In 1734 he received one of the first grants of 500 acres (2.0 km2) from Lord Fairfax, selling some land to Thomas Shepherd, who founded Shepherdstown.

During the American Revolutionary War, local men began drilling in Shepherdstown, and two companies of riflemen were organized in July 1775 at the request of the Continental Congress.

About this time, Fountain Rock, which was then owned by Confederate Colonel Alexander Boteler, was burned by Federal troops under General David Hunter.

By the late 19th century the area was used as a fairground, with its own siding off the Shenandoah Valley Railroad.

In 1900 William Jennings Bryan, then candidate for President, gave a speech to a crowd estimated at 15,000.