Within the city of Winchester:
The First Battle of Kernstown, March 23, 1862
The First Battle of Winchester, May 25, 1862
The Second Battle of Winchester, June 13–15, 1863
The Second Battle of Kernstown, July 24, 1864
The Third Battle of Winchester, September 19, 1864
Near the city of Winchester:
The Battle of Berryville, September 3–4, 1864
The Battle of Belle Grove (or Cedar Creek), October 19, 1864
Winchester was a key strategic position for the Confederate States Army during the war. It was an important operational objective in Gen Joseph E. Johnston's and Col Thomas J. "Stonewall" Jackson's defense of the Shenandoah Valley in 1861, Jackson's Valley Campaign of 1862, the Gettysburg Campaign of 1863, and the Valley Campaigns of 1864. Including minor cavalry raids and patrols, and occasional reconnaissances, historians claim that Winchester changed hands as many as 72 times, and 13 times in one day. Battles raged along Main Street at different points in the war. Both Union General Sheridan and Stonewall Jackson located their headquarters just one block apart at various times.
At the north end of the lower Shenandoah Valley, Winchester was a base of operations for major Confederate invasions into the Northern United States. At times the attacks threatened the capital of Washington, D.C.. The
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