On the evening of October 8, 1864, Gen. Lunsford L. Lomax reached this position with two brigades of Confederate cavalry commanded by Gen. Bradley T. Johnson and Col. William L. "Mudwall" Jackson, while Gen. Wesley Merritt, commanding Union Gen. Philip Sheridan's 1st Cavalry Division of three brigades, lay in camp about three miles north near the base of Round Hill after a week of burning barns, mills, and haystacks and driving off livestock seized from the local population as Lomax cautiously pursued and harassed them under Union Gen. U.S. Grant's directive to "clean out" the Valley. At about 7 a.m., Merritt sent forward his three brigades as Gen. George A. Custer attacked Gen. Thomas A. Rosser's cavalry division south of Toms Brook on the Back Road, while Merritt placed Col. Charles Russell Lowell's Reserve Brigade on the Valley Pike, Col. James Kidd's 1st Brigade to the extreme west in cooperation with Custer, and Col. Thomas Devin's 2nd Brigade on the high ground between the Valley Pike and the Back Road. As the Federals pushed Confederate skirmishers toward this vicinity, Lomax launched a ferocious charge that drove Lowell's Reserve Brigade back in some confusion but exposed the Confederate left flank, prompting Devin to order the 1st N.Y. Dragoons and the 5th U.S. Cavalry to charge that flank as Lowell regrouped and advanced again. Pressed from the front and left, Lomax made a hasty but orderly withdrawal, then formed a defensive position astride the Valley Pike immediately north of Woodstock, where the Confederates were overwhelmed by a Federal charge and fled in disorder to Mount Jackson; in the running fight later nicknamed "The Woodstock Races," Merritt's troopers captured five of Lomax's six guns, more than 50 prisoners and wagons, many horses, and much other equipage.