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Old Town in Winchester, Virginia — The American South (Mid-Atlantic)
 

Winchester During the Civil War

— 1 Story / 1 Thousand Voices —

 
 
Winchester During the Civil War Marker image. Click for full size.
Photographed by Mark P Brock-Cancellieri, August 17, 2025
1. Winchester During the Civil War Marker
Inscription.
"Winchester [was] the key of the region." - John Esten Cooke

Winchester was on the front lines during the Civil War. Valuable to possess, but difficult to hold, it attracted armies, combat, and misery throughout the four long years of conflict.

A key reason for Winchester's importance was the number of major roads that connected here--from north, south, east, and west--roads that drew trade and travel before the war, and opposing armies during it. "Excellent turnpike roads converged upon [Winchester]...like the fingers of an open hand," recalled writer John Esten Cooke. One of those roads was the Valley Turnpike--the interstate highway of its age--which ran right behind you, where the downtown walking mall is today. 250 feet to your left stands the historic Taylor hotel, a famed stopping point for travelers on the Turnpike, and which was used as a headquarters and hospital during the war. And directly in front of your is the 1840 Frederick County Courthouse, the most prominent building in the city, which was used as a barracks, prison, and hospital.

Life was unsettled and uncertain for those who live here. The city changed hands over 70 times, and such sudden changes of fortune could be dangerous. Both pro-Confederate and pro-Union citizens were jailed or expelled from Winchester
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- depending upon who was in control.

Fighting and fear were constant. six major battles and over 50 recorded actions were fought in and around Winchester, and sometimes the city itself became part of the battlefield. During the chaotic closing stages of the Third Battle of Winchester (September 19, 1864), the fighting swept right over the spot where you are standing.

By the end of the war, many residents of the city were long gone, scores of buildings had been destroyed, infrastructure was crippled, and the economy was in shambles.

Made possible by the generous support of Dennis Graham

(captions)
Confederates retreating through Winchester during the Third Battle of Winchester (September 19, 1864). You're standing directly in the path of this tumultuous scene. Sketch by James Taylor. - Image courtesy Western Reserve Historical Society, Cleveland, Ohio.

Civil War Cell Phone Tour
Dial Up History
Call 540-302-2877
The Civil War in Winchester
Stop #21
Call in to the Shenandoah Valley Battlefields Foundation's free cell phone tour to learn more about the Civil War in Winchester.

This detail from a map by Hal Jespersen shows the roads converging upon Winchester at the time of the Civil War.

 
Erected by Shenandoah Valley Battlefields
Winchester During the Civil War Marker image. Click for full size.
Photographed by Bernard Fisher, December 17, 2025
2. Winchester During the Civil War Marker
- National Historic District. (Marker Number Stop #21.)
 
Topics. This historical marker is listed in this topic list: War, US Civil. A significant historical date for this entry is September 19, 1864.
 
Location. 39° 11.066′ N, 78° 9.899′ W. Marker is in Winchester, Virginia. It is in Old Town. It is on North Loudoun Street north of East Boscawen Street, on the right when traveling north. Touch for map. Marker is at or near this postal address: 20 N Loudoun St, Winchester VA 22601, United States of America. Touch for directions.

Regionally, this marker is in Virginia’s Shenandoah Valley. It is also in the American South, specifically in the Upper South, and in the Mid-Atlantic. Globally, it is in the North Atlantic Region, North America, the Western Hemisphere, the Western World, and the Anglosphere. Historically, it finds itself in what was once the territory of the Mississippian Culture, one of the original Thirteen Colonies, one of the Confederate States of America, and the Antebellum South.

Other nearby markers. At least 8 other markers are within walking distance of this marker: George Washington's Political Career Began on This Site (here, next to this marker); Colonel James Wood (here, next to this marker); Lord Fairfax (here, next to this marker); Confederate Memorial (within shouting distance of this marker); History of the Courthouse (within shouting distance of this marker); Jacob H. Yost Building (within shouting distance of this marker); The Wilbur M. Feltner Building (within shouting distance of this marker); A View of Winchester in 1745 - The Four Public Lots (within shouting distance of this marker). Touch for a list and map of all markers in Winchester.
 
Another marker is no longer nearby. Frederick County Courthouse (was within shouting distance of this marker but has been replaced with another marker now near it).
 
More about this marker
Winchester During the Civil War Marker image. Click for full size.
Photographed by Bernard Fisher, December 17, 2025
3. Winchester During the Civil War Marker
The marker is mounted on the wall (lower left)
.
Formerly a tabletop display, the marker is now wall-mounted at the Shenandoah Valley Civil War Museum.
 
 
Credits. This page was last revised on March 18, 2026. It was originally submitted on October 5, 2025, by Mark P. Brock-Cancellieri of Baltimore, Maryland. This page has been viewed 79 times since then and 20 times this year. Photos:   1. submitted on October 5, 2025, by Mark P. Brock-Cancellieri of Baltimore, Maryland.   2, 3. submitted on December 18, 2025, by Bernard Fisher of Richmond, Virginia. • Bernard Fisher was the editor who published this page.
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Jun. 12, 2026