The Fauquier Times-Democrat has a nice little article on US 15, which runs north-south parallel to the mountain here.

In the 17th century, native Americans used the trail, calling it the Great Warriors Path. As settlement increased, the road became a traders route for colonial America, known as the Carolina Road, running from New York to North Carolina.

Soldiers fighting in the French and Indian War, the American Revolution, the War of 1812 and the Civil War all traveled on this route. When the British occupied Washington, D.C., during the War of 1812, the Constitution and the Declaration of Independence were kept at Rokeby, an estate near the Carolina Road.