About Winchester

When European settlers arrived in the Shenandoah Valley around 1729, the Shawnee were the principal occupants in the area around Winchester. During the first decade of white settlement, the Valley was also a conduit and battleground in a bloody intertribal war between the Seneca and allied Algonquian Lenape from the north, and their distant traditional enemies, the Siouan Catawba in the Carolinas.

The settlement of Winchester began as early as 1729 when Quakers such as Abraham Hollingsworth migrated up (south) the Great Valley along the long-traveled Indian Path (later called the Great Wagon Road by the colonists) from Pennsylvania. He and others began to homestead on old Shawnee campgrounds. Tradition holds that the Quakers purchased several tracts on Apple-pie Ridge from the natives, who did not disturb those settlements.

The ridge became affectionately known as Apple Pie Ridge. The Ridge Road built before 1751 leading north from town was renamed Apple Pie Ridge Road. The local farmers found a booming business in feeding the Virginia Militia and fledgling volunteer American army.

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.