Third Winchester was one of the largest battles fought in the Shenandoah Valley and resulted in the wounding and deaths of several important generals on both sides. Federal use of spies provided vital information that led to success in the battle. The battle was an example of well-executed use of a cavalry charge to turn a fixed position. Because of its size, intensity, and result, many historians consider Third Winchester the most important conflict of the Shenandoah Valley.
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After Confederate Gen. Joseph Kershaw’s division left Winchester to rejoin Gen. Lee’s army on the Richmond-Petersburg line, Early renewed his raids on the B&O Railroad at Martinsburg, badly separating his four remaining infantry divisions between Martinsburg and Winchester. On September 19, with the aid of intelligence from a civilian spy in Winchester, Gen. Sheridan advanced towards Winchester through the narrow Berryville Canyon.
Sheridan’s slow movement through the canyon gave Early time to concentrate his forces to meet the initial Federal attacks. The battle continued for several hours with very heavy casualties on both sides. The Confederate line was gradually driven back toward the town but the Confederate troops remained in good order. About mid-afternoon, Federal Gen. George Crook’s VIII Corps along with several cavalry brigades struck the Confederate left flank with tremendous force, breeching the Confederate line and causing panic. Early ordered a general retreat which turned into a rout through the streets of Winchester.