Winchester during the Civil War


Located in the Shenandoah Valley, Winchester was the most contested town in the Confederacy during the American Civil War (1861–1865), changing hands more than seventy times and earning its reputation (in the words of a British observer) as the shuttlecock of the Confederacy. Three major battles were fought within town limits and four others nearby. In 1862, Confederate general Thomas J. “Stonewall” Jackson won a victory there during the Shenandoah Valley Campaign that solidified his reputation as the Confederacy’s first hero. Following Jackson’s death in May 1863, Richard S. Ewell took over his corps and, on the way to Gettysburg, scooped up the Union garrison at Winchester, suggesting to many that he might have the stuff to replace the fallen Stonewall. The Third Battle of Winchester (1864) was a Union victory, part of Union general Philip H. Sheridan‘s successful Valley Campaign against Jubal A. Early. The war, meanwhile, brought huge changes for the town’s residents, including rampant inflation, often harsh measures imposed by occupiers, and the destruction of slavery. By 1865, the town was largely destroyed.


Chartered in 1752, Winchester served as the seat of Frederick County and was an important market center during the nineteenth century. Nine roads and turnpikes and the Winchester and Potomac Railroad tied the city to the North and a developing national economy, but the presence of slavery linked Winchester to the South. In 1860 Winchester’s population was about 4,400, including 706 enslaved and 665 free black people.

When war broke out, Winchester’s location and function as a rural market center ensured that it would be coveted by both sides in the conflict. Possessing Winchester would be crucial to controlling the Shenandoah Valley’s abundant agricultural resources. Further, possession of Winchester had broad strategic implications. A Confederate army in Winchester would be north of Washington, D.C., and could threaten the capital or open the way to an invasion of Maryland or Pennsylvania. A Union army in Winchester, meanwhile, could jeopardize Confederate general Robert E. Lee’s extended left flank and his ability to protect the Confederate capital at Richmond. One historian aptly described Winchester as “the key that locked the door to Richmond.” As much as Winchester was a prized target, it proved especially difficult to keep. The town was surrounded by low hills that easily masked approaching armies, and neither side was successful in holding it against an approaching foe.

Winchester was relevant to several significant military operations during the course of the war. The town was the site of an important Confederate victory on May 25, 1862. This First Battle of Winchester was part of Stonewall Jackson’s Shenandoah Valley Campaign, which served to distract Union troops from reinforcing George B. McClellan outside Richmond. The Second Battle of Winchester, on June 13–15, 1863, helped to secure the Shenandoah Valley for Lee’s army as it mounted its second invasion of the North. The Third Battle of Winchester, on September 19, 1864, was a defeat for Confederate forces under Jubal A. Early and part of Philip Sheridan’s notorious reclamation of the Shenandoah Valley.

Military Occupation

While local historians boast that Winchester changed hands more than seventy times during the war, estimations of full-fledged occupations by either army range from eleven to thirteen. Wartime diaries suggest that Winchester was under Confederate authority for 39 percent of the war, occupied by Union armies for 41 percent of the war, and between the lines for 20 percent of the war. As a result of continued frustration in the Shenandoah Valley and evolving military policy, each successive Union occupation resulted in harsher measures toward civilians. Initially individuals were hassled and homesteads plundered. In the spring of 1862, Union general Nathaniel P. Banks attempted to placate Winchester’s population. Union general Robert H. Milroy, however, admitted he felt “a strong disposition to play the tyrent among these traitors,” embittering residents with his harsh policies throughout the first half of 1863. He required citizens to take oaths pledging their allegiance to the United States. If they refused, soldiers would quarter their homes. Milroy also permitted Union troops to obliterate Winchester, refusing to interfere when they razed every unoccupied house in town. Although Union general Philip H. Sheridan has an infamous reputation in the Shenandoah Valley, his occupation of Winchester in the autumn of 1864 brought some much-needed stability to the town.

Winchester residents quickly learned that the presence of either army had unpleasant consequences. In the summer of 1861, as Confederate troops inundated the town, one resident characterized Winchester as “a smelly dirty place.” Another noted that “15,000 Troops are around and about us. Nothing but soldiers—soldiers.” Diseases ran rampant, with approximately 2,000 soldiers sick with measles and mumps being housed in private dwellings. Most periods of Confederate control resulted from major battles, and on such occasions wounded soldiers overwhelmed the town. Residents estimated that between 3,000 and 5,000 wounded soldiers recuperated in Winchester after the Battle of Antietam in the autumn of 1862. “Every house is a hospital,” a resident observed at the time.

Inhabitants of occupied Winchester faced increasing economic hardship. By the end of 1861 inflation was rampant; salt that sold for $8 a sack in August cost $20 by December. The mid-October 1863 price of flour was $12 per barrel. By November 1864, flour was $50 for three barrels ($50 in greenbacks, rather than in hyper-inflated Confederate currency). One resident recalled, “People used to have a basket to carry their money to market in but it bought so little they could carry the provisions home in their pocketbooks.” Union occupations magnified this hardship by requiring buyers to take an oath of allegiance to the United States, which many residents refused to do. Winchester’s proximity to large armies quickly took its toll; in July 1863 Robert E. Lee wrote to his wife, “Poor Winchester has been terribly devastated, & the inhabitants plundered of all they possessed.”

Union occupations also contributed to the destruction of slavery in Winchester. Many slaves took advantage of Union military occupation to escape bondage, and even those who remained enjoyed increased autonomy when Union forces were present. Refugee slaves from the countryside entered Winchester in droves after the entrance of the Union army. One month after the first Union occupation, diarist Mary G. Lee noted that “[t]he freedom of the servants is one of the most irritating circumstances” of the Union military presence. In April 1864 a black Union regiment came to Winchester on a recruiting mission; while some men joined, the mission was largely unsuccessful. When Confederates swiftly returned to Winchester in 1862, 1863, and 1864, they captured many local slaves and returned them to their owners.

Winchester Civilians

During the war and after, Winchester enjoyed a reputation as a secessionist stronghold. After a visit to the town in the spring of 1862, U.S. secretary of state William H. Seward observed, “the men are all in the army, & the women are the devils.” As Seward’s comment suggests, much of the resistance to Union occupation came from the town’s women. One Shenandoah Valley historian asserted that discussing “Winchester” during the war really meant discussing the women of Winchester. Resident Mary G. Lee concurred with these assessments, boasting “This is surely the day of women’s power.”

Women adopted tactics like wearing what became known as “Jeff Davis”—after Confederate president Jefferson Davis—or “secession” bonnets, which hid their eyes from the gaze of Union soldiers. Many refused to walk under the American flag, and some berated Union troops verbally. Jedediah Hotchkiss, a mapmaker from Staunton on Stonewall Jackson’s staff, heard that “our women there are not afraid of [Union troops] and tell them freely what they think of their conduct.” Their fury against the invaders reached its height during the First Battle of Winchester, when several Union units reported instances of women firing at them as they retreated through town. A member of the 7th Ohio Infantry concluded that “Charleston, South Carolina could not furnish a female and juvenile population imbued with more bitter sentiments towards the North and her soldiers than this city.”

Despite Winchester’s secessionist reputation, the town was home to a significant minority of Unionists. Estimates of Unionist strength in Winchester vary from a dozen families to several hundred individuals. On the eve of the first Union occupation of the town, Hotchkiss declared that while the Confederate army had many supporters in Winchester, there were “hundreds who desired the yankies to come in.” The strength of Unionism varied according to the military situation in town—Unionism was stronger during Union occupation and more circumspect during times of Confederate control. Perhaps the most well-known Unionist was Rebecca Wright, who supplied Sheridan with information on Confederate strength and troop positions before his attack at the Third Battle of Winchester. While some residents remained staunch secessionists or Unionists throughout the war, many became more guarded as the conflict continued. One Union soldier observed, “So often had this portion of the Valley changed hands, that even the women had learned the policy of reticence, the most difficult task imaginable to a woman thoroughly imbued with the doctrine of ‘secession.'”

Winchester and the Valley Army

One of the distinctive aspects of Winchester’s Civil War experience was the relationship between its residents and its defenders. Winchester and Frederick County contributed several companies to the regiments of the Stonewall Brigade. A reporter for the Baltimore American noted that “[s]carcely a family in the town but has one or more relatives in Jackson’s army.” One historian of the Shenandoah Valley observed that frequently soldiers of the Stonewall Brigade fought and died “almost within sight of their homes.” Another scholar asserts, “In few wars have the soldiers maintained as intimate contact with their homes and with the community from which they came as did the valley soldiers.”

The brigade’s commander, Stonewall Jackson, enjoyed a stellar reputation among Winchester residents. Jackson and his wife Mary Anna spent the winter of 1861–1862 in town and endeared themselves to the townspeople. Many inhabitants perceived Jackson as their personal guardian; his stunning return to Winchester on May 25, 1862, solidified his status among the town’s residents. Jackson called his reception in Winchester on that day “one of the most stirring scenes of my life.”

While Jackson’s death following the Battle of Chancellorsville in May 1863 was mourned throughout the Confederacy, it cast an especially strong pall over Winchester. After learning of Jackson’s death, Mary G. Lee despaired, “A gloom, still deeper, is over our whole town … we feel that no one cares for us now; while Jackson lived we were honoured by his especial regard & remembrance & we knew he loved Winchester & loved to drive off our invaders.” A few days later Lee observed that in Winchester, Jackson’s name was synonymous with “every thought of deliverance.”


Like most of the lower Shenandoah Valley, Winchester was devastated by four years of active warfare. In the town and its immediate surroundings, more than 200 homes were missing at war’s end; a hundred more were used as stables and hospitals, suffering considerable damage. A postwar editorial reported that “every building that survived the torch, both in the city and county, was more or less out of repair.” Winchester gradually recovered from its wartime ordeal but never regained its prewar prominence in the region.

As they had during the war, the secessionist women of Winchester toiled to make sure that the Confederate cause remained prominent among residents after the fighting ended. In May 1865, they organized the Ladies’ Memorial Association to collect and reinter the remains of Confederates scattered throughout the region. Their efforts resulted in the dedication of the Stonewall Cemetery in October 1866. The cemetery holds the remains of 2,489 Confederate soldiers, including Turner Ashby and his brother Richard.

March 12—May 25, 1862
Union troops under Nathaniel P. Banks occupy the Shenandoah Valley town of Winchester.
March 23, 1862
Confederate forces are defeated at the Battle of Kernstown. After the battle Winchester civilians bury the Confederate dead.
May 25, 1862
The First Battle of Winchester results in a Confederate victory. Confederate general Thomas J. "Stonewall" Jackson's Valley Army occupies the Shenandoah Valley town of Winchester.
June 4—September 2, 1862
Union troops under Franz Sigel occupy the Shenandoah Valley town of Winchester.
September 3—December 13, 1862
Confederate forces occupy the Shenandoah Valley town of Winchester.
December 24, 1862—June 13, 1863
Union troops under General Robert H. Milroy occupy the Shenandoah Valley town of Winchester.
June 14, 1863
Confederate troops under General Richard S. Ewell drive Robert H. Milroy's Union troops out of town in the Second Battle of Winchester.
September 19, 1864—April 9, 1865
Union troops under Philip H. Sheridan occupy the Shenandoah Valley town of Winchester.
September 19, 1864
Union troops under General Philip H. Sheridan defeat General Jubal A. Early's Confederate forces at the Third Battle of Winchester.
  • Colt, Margaretta Barton. Defend the Valley: A Shenandoah Family in the Civil War. New York, New York: Crown Publishers, Inc., 1994.
  • Duncan, Richard R. Beleaguered Winchester: A Virginia Community at War, 1861–1865. Baton Rouge: Louisiana State University Press, 2007.
  • Mahon, Michael, ed. Winchester Divided: The Civil War Diaries of Julia Chase & Laura Lee. Mechanicsburg, Pennsylvania: Stackpole Books, 2002.
  • McDonald, Cornelia Peake. A Woman’s Civil War: A Diary, with Reminiscences of the War, from March 1862. ed. Minrose C. Gwin. New York, New York: Gramercy Books, 2003.
  • Philips, Edward H. The Lower Shenandoah Valley in the Civil War: The Impact of War Upon the Civilian Population and Upon Civil Institutions. Lynchburg, Virginia: H. E. Howard, Inc., 1993.
  • Phipps, Sheila R. Genteel Rebel: The Life of Mary Greenhow Lee. Baton Rouge: Louisiana State University Press, 2004.
APA Citation:
Berkey, Jonathan. Winchester during the Civil War. (2020, December 07). In Encyclopedia Virginia. https://encyclopediavirginia.org/entries/winchester-during-the-civil-war.
MLA Citation:
Berkey, Jonathan. "Winchester during the Civil War" Encyclopedia Virginia. Virginia Humanities, (07 Dec. 2020). Web. 21 Jul. 2024
Last updated: 2024, May 03
  • This field is for validation purposes and should be left unchanged.