Hupp's Hill played a significant role throughout the Cedar Creek operation. Jubal Early's entire force showed itself here on 13 October in an effort to draw the Federals into battle from their positions north of Cedar Creek. Union positions across Cedar Creek were fired on by Confederate artillery. The Federal First Division, VIII Corps attacked across Cedar Creek and a sharp fight ensued. The Federal brigade commander was killed and his forces lost over 200 men. Conner's Brigade of Kershaw's Confederate Division lost nearly 180 men and Brigadier General James Conner was seriously wounded. This engagement took place mostly between Cedar Creek and the Signal Knob Restaurant on US 11.
Early withdrew to Fisher's Hill the night of 13 October but each day thereafter he sent out a brigade to Hupp's Hill to observe Federal activities. General John B. Gordon came to Hupp's Hill on 17 October in order to begin planning for an attack. He ruled out an attack down the Pike because of the evident frontal strength of the Federal positions.
By 0430 on the morning of 19 October, Wharton's Division had moved up to Hupp's Hill from Fisher's Hill to be in a position to support the main attack farther east. When Wharton heard Kershaw's attack open, he moved forward to Stickley Hill and then to Cedar Creek. At about the same time, the Confederate artillery under Colonel Tom Carter rushed from Fisher's Hill to Hupp's Hill and began firing on Federal positions by about 0515. It moved to positions north of Cedar Creek after 0600.
The I-81 interchange is close to the crest of Stickley Hill where Confederate rear guards vainly tried to establish a second of three defensive lines on the evening of 19 October. Later, George Custer positioned himself on Stickley Hill to direct the movement of his regiments against the retreating Confederates. He was joined there during the pursuit by Colonel Thomas C. Devin of Merritt's Cavalry Division. Captured Confederate materiel was collected on Stickley Hill first before being taken to Belle Grove.
During the Confederate retreat, Bryan's Virginia Battery tried to establish a defensive position on Hupp's Hill. It was aided by a motley group of infantrymen gathered by Major Henry Kyd Douglas, one ofJubal Early's aides. They tried to establish a blockade of fence rails and debris across the Pike (US 11) but soon were overwhelmed by the Federal cavalry.
Late on the night of 19 October, Hupp's Hill was occupied by Federal units from the First Division, XIX Corps. It was relieved the next day by the Second Division, VI Corps. It was this unit which dug the earthworks visible today. They were laid out and their construction supervised by Major Hazard Stevens, the corps adjutant general. This division remained here until 10 November 1864 when Sheridan pulled his entire army back to Winchester.
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