September 19, 1864
Lieutenant General Jubal Early's Shenandoah Valley Campaign began in June of 1864. Until the Third Battle of Winchester on September 19, he more than fulfilled General Lee's hopes that the great success of 1862 could be repeated in 1864.
Early's opponent, General Philip Sheridan, assumed command of the Army of the Shenandoah on August 7, 1864. By September 19 its strength was just under 40,000 men. Sheridan's mission, entrusted to him by General Grant and President Lincoln, was to end Lee's diversionary campaign by driving Early from the Valley and destroying what would prove to be the Valley's last wartime harvest and all military or civilian assets that benefited the Confederacy.
Historians have compared the Valley Campaign of 1864 with Jackson's in 1862. Both campaigns climaxed in battles at Winchester. The essential difference was in General Lee's ability to reinforce his Valley lieutenants at the crucial moment of their campaigns. In May 1862 he could, but in September 1864, he could not. In fact on September 14, 1864, Anderson's infantry division and an artillery battalion departed the Valley for Lee's army at Petersburg, leaving just 15,200 men to oppose Sheridan.
Sheridan learned of the departure of these troops from information furnished by a resident of Winchester. More importantly, he learned from his own cavalry patrols north of Winchester that Early had finally made an error: immediately following Anderson's departure from the Valley, Early unwisely divided his forces. Leaving only General Ramseur's small division east of Winchester, guarding the Berryville Pike. Early moved three remaining divisions north, in the direction of the main line of the B & O Railroad at Martinsburg. Sheridan immediately prepared to attack. Sheridan's plan was to destroy Ramseur's division east of Winchester while crossing most of his cavalry over the Opequon downstream (north) of his Berryville Pike crossing. While his cavalry congregated at Stephenson's Depot near the Valley Pike, his infantry would face north and defeat each of Early's divisions as they hastened back to save Ramseur.
The battle that raged from dawn to dusk on September 19 was the biggest and bloodiest of the battles in the Shenandoah Valley. Sheridan's plan miscarried. Ramseur's division eluded destruction, falling back on Winchester. Rhodes' and Gordon's divisions reinforced him quickly. In fact, Confederate counterattacks near the Berryville Pike came close to shattering Sheridan's far larger force. In mid-afternoon, an audacious plan to turn Early's left, then anchored at the Hackwood Farm east of here, narrowly failed; the battle seemed to be a bloody stalemate. Sheridan had one card left to play - his cavalry, concentrated around Stephenson's Depot. There were few Confederate forces in Fort Collier, now the anchor of the last Confederate line of battle. The open fields, bisected by the Martinsburg Pike and stretching from Stephenson to Fort Collier, were idea terrain for large cavalry operations. After a long and bloody day of fighting, with the sun setting in a reddening sky, six Federal cavalry brigades began the advance up to the Martinsburg Pike toward Fort Collier. The battle hung in the balance.