The Battle of Guard Hill or Battle of Crooked Run took place on August 16, 1864, in Warren County, Virginia as part of Philip H. Sheridan’s Shenandoah Valley Campaign of the American Civil War. According to Pachan, the Union’s superior numbers and quality leadership routed the Confederate infantry, and the battle proved a watershed event in the Shenandoah Valley campaign.
On the morning of August 16, Confederate troopers scattered the Federal pickets at the Shenandoah River crossing at Front Royal. The troopers pursued them down the Front Royal Pike, eventually coming to Guard Hill, a prominent landmark. There, they were hit by Union Brig. Gen. Thomas C. Devin’s dismounted cavalry brigade and sustained heavy losses. Confederate Brig. Gen. William T. Wofford’s brigade attempted a flanking movement by wading across Crooked Run. There, they were attacked by two New York brigades, who took 300 of them captive. Union Brig. Gen. George A. Custer’s Michigan Brigade rode toward the battle and sustained Devin’s line along Crooked Run until they were forced to withdraw to Cedarville by Confederate artillery now on Guard Hill.