The earliest known use was as part of a trail of the Native Americans, and, named for Thomas Ashby, it later became part of a series of roadways, eventually becoming the crossing of the Blue Ridge for U.S. Route 50.
The earliest known use was as part of a trail of the Native Americans. Later it came to be called Ashby's Gap, and eventually became the crossing of the Blue Ridge for Millwood Pike, which is modern U.S. Route 50.