Ashby’s Gap is a wind gap (that is, no stream flows through it) in the Blue Ridge Mountains at the intersection of Farquier County, Loudoun County and Clarke County in Virginia. (39.017983° N, 77.966723° W)

The gap reaches an altitude of 1,027 feet. This is about 500 feet below the main ridgeline and about 700 feet above the Shenandoah River, just to its west.

The gap was a major trail for Native Americans. It was originally known by European colonists as the Upper Thoroughfare of the Blue Ridge. It took its present name from Thomas Ashby, who owned land on the east side of the gap and helped settle Parris, Virginia.

Before the Civil War the Ashby’s Gap Turnpike operated a paved toll road that ran from Aldie to the crest of the Blue Ridge. It was a major route from Virginia’s Piedmont region to the Shenandoah Valley. The turnpike became today’ s U.S. Route 50.

The Confederate Army of the Valley under Joseph Johnston marched through Ashby’s Gap in July of 1861 on the way to board trains at Piedmont Station (known today as Delaplane) on the way to the First Battle of Manassas (Bull Run).

In June of 1863 Confederate cavalry under J.E.B. Stuart held the gap against probing Union forces to cover Lee’s Invasion of Pennsylvania that led up to the Battle of Gettysburg.