In the summer of 1864, General-in-Chief Ulysses S. Grant knew that Washington, D.C., remained vulnerable if General Jubal A. Early's army was on the loose in the Shenandoah Valley. In August, Grant named his aggressive cavalry commander, General Philip Sheridan, to command Union forces in the valley. Sheridan’s campaign to rid the valley of Confederates got off to a rough start, nearly falling victim to attacks at Front Royal on August 16 and Summit Point on August 21. As Sheridan slowly moved south up the valley, there were inconclusive skirmishes with Early’s men at Smithfield Crossing on August 29 and Berryville on September 3.

On September 19, Sheridan advanced toward Winchester along the Berryville Pike and met Early’s army east of town. The largest battle ever fought in the Shenandoah Valley raged all afternoon. Early was forced to retreat to Strasburg and took up a defensive position on Fisher’s Hill. On September 21, Sheridan attacked, driving back defenders and forcing Early to retreat again the next day. As Early fell back to Staunton, Sheridan’s men destroyed everything of value to the Confederate army in a 5-day period known as “The Burning.”

Reinforced with cavalry, Early pursued Sheridan as he moved northward. Union cavalry attacked their Confederate counterparts at Tom’s Brook on October 9, and again Early’s defeated troopers retreated south. Early executed a surprise attack against Sheridan’s army at Cedar Creek on October 19. Sheridan’s timely arrival on the battlefield to rally his retreating men saved his army and led to the massive counterattack that nearly destroyed Early’s force. Sheridan’s victories over Early extinguished hopes of Confederate offensives in the Shenandoah Valley, and were important Union victories that helped ensure President Abraham Lincoln's reelection in November.