Winchester in the Civil War

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 in return.


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.


'Tour the Winchester Area' shows the many places where you can see reminders of the Civil War around Winchester. Many of these are simple markers or memorials, but over the years a number of organizations have preserved sizable tracts of land and even structures that allow the visitor to better understand what hapened on these fields.


The 'Civil War Winchester Timeline' is an important tool to 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.


And finally, 'Tour the Shenandoah Valley' helps put into perspective the great chess games played out in the Valley that eventually turned this beautiful region into a wasteland.


Photos at right:
(top) Pritchards Hill on the Kernstown battlefield
(center) First Battle of Winchester markers on Jubal Early Drive on the south side of Winchester
(bottom) Civil War Trust wayside marker on the Third Winchester battlefield.

About the Author • ©2007-2014 Steve Hawks