Winchester is in the northern, or lower, Shenandoah Valley. Formed by the Alleghenies to the west and the Blue Ridge to the east, the Valley shelters the Shenandoah River on its journey down to the Potomac at Harpers Ferry.
The Valley’s natural corridor formed by the river also spawned the 19th century Valley Pike (modern-day US 11), along which both commerce and armies traveled. In contemporary times, Interstate 81 has replaced the Pike as the principal transportation route, bringing both opportunities and challenges to the interpretation of Civil War history.
To the embattled and hard-pressed South, the Shenandoah Valley was a land of plenty—filled with grain, dotted with mills and linked by road and rail with a main theatre of war across the Blue Ridge. The Valley also had abundant strategic options to offer to Confederate gnerals.
Indeed, as Gen. Thomas J. “Stonewall” Jackson said, “If this Valley is lost, Virginia is lost.”
As a gateway to the Valley, Winchester became a battleground from the very beginning. Despite its great importance—or because of it—Winchester proved impossible to defend. The number of times the town changed hands during the war—perhaps more than 72 times—is today a matter of local pride.
Today, vestiges of the Civil War remain in Winchester and Frederick and Clarke Counties. The voices of wounded and captured soldiers echo through the county courthouse, where their graffiti is still visible. The courthouse is now a museum open to the public, as is the house that served as Stonewall Jackson’s Headquarters the winter before his famous 1862 Valley Campaign. Throughout the region, historic farms, homes, mills, and cemeteries, along with outstanding museums and interpreted sites, all help tell the powerful history and moving legacy of the war.
Visitors can walk the battlefields at Kernstown, Cool Spring, and Second and Third Winchester and learn how Jackson, Robert E. Lee, Jubal Early, and Philip Sheridan shaped the course of the war. Scattered throughout the region are the stories of the war’s effect on the Valley’s civilian population—how these families survived the personal and economic devastation that war brought, and how they rebuilt their lives in the years after the guns fell silent.
To visit those sites today, you may want to begin your journey at the National Historic District Civil War Orientation Center for the area, housed in the Winchester-Frederick County Visitor Center, which can help guide you to the host of sites where you can experience the region’s dramatic Civil War story today.