Ashby's Gap, located on the crest of the Blue Ridge Mountains, was first called "the Upper
Thoroughfare of the Blue Ridge", but after Thomas Ashby received land on Goose Creek at
its junction with Crooked Run (the present site of Delaplane), and later settled near what
is now Paris, it became known as Ashby's Bent, and still later as Ashby's Gap. This Thomas
Ashby was a prominent citizen both there and in Frederick County where he subsequently
lived. His son John Ashby was a noted Indian fighter and bore to the Governor at
Williamsburg the dispatches telling of Braddock's defeat and death.
Ashby's Gap was a strategic focal point for both sides in the
Civil War because of its
proximity to Winchester and the fact that whichever side controlled the Gap also
controlled access to the northern end of the Shenandoah Valley from the east.