The earliest known use of the gap was as part of a trail of the
Native Americans. The gap was first referred to as the "Upper Thoroughfare of the Blue Ridge". It was later named "Ashby's Bent" when Thomas Ashby received lands along Goose Creek, and settled
Paris, Virginia, at the eastern entrance to the gap. Later it came to be called Ashby's Gap. In the early 19th century the
Ashby's Gap Turnpike was completed from
Aldie to the crest of the gap where it met up with the Millwod Pike. Those roads in turn became the modern U.S. Route 50 in 1922 when the Commonwealth took possession of them.
Importance during American Civil War During the
American Civil War, Ashby's Gap was often used by the
Confederate Army and
Union Army in the several Shenandoah Valley campaigns. The nearby ridgetop was used by the
Confederate Signal Corps. In July 1861
Brigadier General Thomas J. "Stonewall" Jackson led his
1st Virginia Brigade through Ashby's Gap on his way from
Winchester to Piedmont Station (present day
Delaplane) where they boarded railcars on the
Manassas Gap Railroad and were taken to
Manassas Junction where the
First Battle of Manassas was underway. This marked the first use of railroads for troop movement in a war. In June 1863, Confederate
Major General J.E.B. Stuart's
cavalry held this gap to prevent elements from the Union Army under Major General
Joseph Hooker from interfering with
General Robert E. Lee's army as it marched north toward
Pennsylvania in the
Gettysburg campaign. On July 19, 1864, a small cavalry battle, sometimes referred to as the Battle of Ashby's Gap (part of the larger
Battle of Cool Spring), was fought at the gap when Union cavalry attempted to force passage across the gap and Shenandoah River in an attempt to attack the rear of Confederate
Lieutenant General Jubal Early's army and supply trains as he repositioned himself near
Berryville as part of the
Valley Campaigns of 1864. ==References==