Winchester was the largest city in the Shenandoah Valley during the Civil War. It was a strategic crossroads that repeatedly saw armies clashing in battle, including ‘Stonewall’ Jackson’s first battle as an army commander and the largest battle fought in the Shenandoah Valley. Many of these fights have more than one site in the Winchester area. Some sites are shared by more than one battle. Markers for several battles may often stand side by side.

Map of Civil War sites around Winchester, Virginia

Winchester is the site of the Winchester National Cemetery and Stonewall Confederate Cemetery (part of Mount Hebron Cemetery), the final resting place of several thousand Civil War soldiers.

Stonewall Confederate Cemetery
Winchester National Cemetery

A brief background of Winchester, Virginia

Winchester, Virginia is filled with history. What would come to be called the Great Wagon Road brought the first European settlers here in the early 1700s. George Washington’s headquarters was here during colonial days – you can still see it – and it was here where he first stood for elected office.

The Civil War wrote several major chapters of this history. The Great Wagon Road had grown into the Valley Pike, an all-weather paved highway up and down the valley. Other major roads led to tidewater Virginia to the east and the mountains to the west. A railroad connected with the Baltimore & Ohio at Harpers Ferry. Winchester was a crossroads that dominated travel in any direction across the lower Valley – and crossroads attract armies.

They also attract generals. ‘Stonewall’ Jackson made his headquarters here, too – which you can also still see. He liked the town so much he brought his wife to live with him for a time. He hoped to return to Winchester to live after the war. A series of Union generals – Banks, Milroy and Sheridan – also made Winchester their seat of command, although none loved it so much, or were so highly regarded by the townspeople.

So many battles were fought around Winchester that they have been numbered: First and Second Kernstown. First, Second and Third Winchester (or Opequon). It can be a challenge to keep track of what happened in what year where, and how it fits in with the bigger picture. The Civil War Winchester Timeline can help sort out when the many events happened in Winchester and how they fit into the Civil War. It is also an interesting study in how many times the city changed hands in two and half years.