Chester Gap was a mountain pass of strategic importance throughout the Civil War, occupied and traversed numerous times by Union and Confederate forces. Its first significant use came from July 7-18, 1862, when Gen. Nathaniel Bank’s corps of the Union Army of Virginia marched through on the way to a month-long occupation of Rappahannock County. In the months after the Battle of Antietam in the autumn of 1862, Federal and Confederate armies contested control of the Blue Ridge passes, and from October 28 to mid-November intense skirmishing took place in and near Chester Gap as Confederate Gen. D.H. Hill’s division occupied the gap and demonstrated at Thornton Gap before moving to Fredericksburg with Gen. Thomas J. “Stonewall” Jackson later in November. Chester Gap also played a critical role for Confederates during the Gettysburg Campaign in both the advance and retreat, with two-thirds of Gen. Robert E. Lee’s Army of Northern Virginia passing through it and many units camping there. On the night of December 19, 1864, Union Gen. Alfred T.A. Torbert and 5,000 cavalrymen bivouacked there during a raid on Gordonsville intended to disrupt the Virginia Central Railway, but horrible sleet and rain left many soldiers suffering from frostbite and exposure, and the raid failed before the troopers returned to Winchester on December 28.
