Liberating Winchester?

On Sunday, May 25, 1862, the Confederate soldiers in General Thomas J. Jackson’s army who had stayed in the ranks through the grueling night march found themselves on the high ground surrounding Winchester, Virginia, and extending toward the east and west. After the Confederate victory at Front Royal on May 23, Jackson left General Richard Ewell to push his column from Front Royal to Winchester. Jackson took another column and joined Turner Ashby’s cavalry along the Valley Pike, also pushing north toward the small city. Union General Bank’s army was on the run, and “Stonewall” wanted to keep up the pursuit. Driving his columns forward through the night with the determination to reach the high ground near Winchester ultimately paid off, and in the morning fog, Jackson readied to launch his weary soldiers toward the town. At daybreak, the attack began. After a couple hours of fighting on the outskirts of town, Banks and his blue clad army retreated, fleeing out the north side of the town as Jackson and the hollering rebels entered at the other side. Pockets of resistance were quickly overwhelmed, and some local civilians brought their pistols to the windows and took potshots at their hated “oppressors.” As the Confederate officers and soldiers charged or marched through the streets, the civilians came out to their doorsteps to welcome back the general and army that had “abandoned” them the previous March.

“Jackson Enters Winchester” by Mort Kunstler (

Popular art depicts General “Stonewall” Jackson’s return to Winchester, Virginia, on May 25, 1862, in bright and vivid colors. Mort Kunstler’s piece, especially draws a rosy-hued scene of joyous civilians rushing to the streets and cheering the general and his men, giving them bouquets of flowers. It is fine art, and from personal experience, it can be reported that it captured the imagination of an impressionable teenager. A first glance at primary sources even lend support to the image. Southern sympathizing civilians in Winchester met the Confederate army with frenzied excitement and recorded it in their diaries. Laura Lee celebrated on paper, using 18 exclamation points: “Thanks be to the Lord, we are free!!!!!!!!!!!!!!!!!!”[i]

The Confederate return to Winchester during the 1862 Valley Campaign marked a military success, but more outcomes came from the moment. More than roads and troops converged on Winchester that day. Ideas clashed too. Civilian observers took different views of the day based on their allegiances. Confederate officers and soldiers in the ranks still had differing opinions about their commander, even as he began to morph from “Old Tom Fool” to “Mighty Stonewall” in their minds and certainly in their memories of the war, and Jackson himself felt conflicted about the success of the day. The words “free” and “freedom” used so happily by Confederate civilians to celebrate their military liberation meant something very different to enslaved and freedmen caught in the same battle storm. Finally, the glorious day for the pro-Southern civilians also held its tragedies, as soldiers enlisted from their own community were carried home dead or wounded. Fine art has its purposes, but the primary sources surrounding the “liberation” (to borrow the Confederate phrase) reveal deeper, darker conflict tinging the scene on that historic Sunday in Winchester.

Civilians in the small city in the lower (northern) Shenandoah Valley had a mix of allegiances. Most white people leaned pro-Confederate since April 1861, but there were a few with Unionist loyalties. Jackson’s winter stay had created friendly ties between the commander and the supportive civilians, and many had friends and relatives in the Stonewall Brigade or other units in Stonewall’s command. However, one of the wars within the war on Winchester’s homefront smoldered between the civilian sympathies. While some Southern women took shots from windows or doorways at retreating Union soldiers and celebrated the Confederates’ return enthusiastic, women like Julia Chase told a very different story in their journals: “Oh, what an awful day tis has been. God grant I may never see the like again. The Confederate Army are in full possession of Winchester again. Gen. Banks has retreated in great disorder — why did he not act differently. Me thinks the women could have managed affairs better….”[ii]

Jackson himself had mixed reactions to his success at Winchester. Though thrilled to “liberate” his civilian friends, score a military victory, and capture needed supplies, he chaffed that he could not effectively follow up his attack with a decisive pursuit. He tried, though, and Confederate troops advanced about 5 miles beyond the town before Jackson called a halt. The roadways were too crowded with the Union’s abandoned wagons and an effective rear guard rallied and encouraged by General Bank’s himself. Instead, Jackson returned to town and fell asleep at the Taylor Hotel, a testament to his own exhaustion which mirrored that of his men, but a fact that did not translate well to later fine art depictions. [iii] The lack of organized cavalry caused trouble, and Jackson later bemoaned that fact, though he had begun to realize that Turner Ashby was gallantly unreliable. Ultimately, “Stonewall” had to settle. He had recaptured Winchester (temporarily). He had put Bank’s army in retreat toward the Potomac River. And he had captured a huge quantity of much-needed supplies, including 9,354 small arms with 500,000 rounds of ammunition, 34,000 pounds of food supplies, and $125,185 worth of other military equipment.[iv] Those points alone were something to cheer about from the Confederate viewpoint.

William D. Washington’s imaginative artwork of Jackson during the Valley Campaign illustrates the hero’s place Jackson held in Winchester and includes a stylized image of Little Sorrel.

In their exultant cries on the streets and later in their private diaries, Winchester women celebrated the freedom they felt, the liberty from their Yankee oppressors. But while they celebrated, another group of civilians trembled in fear and decided to leave to find freedom for themselves. David Hunter Strother, a Virginia loyalist with General Bank’s army, left Winchester with the rest of the Union army and vividly described the scene of enslaved men, women, and children making the choice to leave bondage and face a terrifying and uncertain future.

“In the meantime the scenes along the road were pitiable and ludicrous. Droves of Negroes increasing at every step thickened the column.” He described a large older woman and a younger mulatto woman “dragging a heavy baby” and “weeping and gesticulating, ‘O Lord, they will kill us. They will kill us.’ ….Here half a dozen light wagons loaded with plunder and sprawling with babies were shoved out of the road to make room for a battery. Every black face wore an agonized and anxious expression. They said that Jackson had sworn to kill them all if he ever came back to this valley, which they seemed to believe religiously. Yet their masters [had] tried to impress them with the belief that the Union troops would kill them if they got them. This latter story they did not accept at all and hence the retreat of the army. All that could move at all took up their bundles and walked, doubtless despoiling their masters as they left of everything they could lay their hands on. As the cannonade in our rear would increase, their bundles and stuffed pillow cases strewed the wayside. Broken wagons and dead horses now occasionally stopped the trains and were dragged aside….”[v]

Since the Emancipation Proclamation had not entered the war aims in May 1862, the African Americans looking for freedom and following the army on the road toward the Potomac River relied on the “contraband of war” principle which had been established the previous year. Even under the semi-protection of the retreating army, their status and future looked tenuous and most faced challenges in the weeks ahead as they navigated freedom for the first time and left behind the streets and homes of Winchester.

While some Confederate soldiers found it exciting to recapture their hometown, the opportunity also set the stage for grim tragedy. In her diary, Southerner Laura Lee recorded:

“Our army was pouring through the town in pursuit on every street, Gen. Jackson heading them, when he found the enemy were running so fast, he ordered all on in the pursuit, even the artillery were allowed to unhitch their horses and mount and follow By this time a rumor reached us that Marshall Barton was killed. David (his brother) rode up and said all were safe but Marshall who he told his was badly wounded, that they must send to him at once, but he whispered to Luke that he was already dead. He told us too that Bob McKim was killed. We were greatly shocked and saddened to hear of both…. Sometime after breakfast Marshall’s body was brought home. He was shot near Mr. Hollingworth’s and was carried there. He lived half an hour, and Mrs. H. said his last words were “Mother, Mother.” Mrs. Barton has borne it nobly. She says she gave her sons to her country, and she must not murmur at the sacrifice. She stayed downstairs all day Sunday, feeding the starving soldiers as they came back from the pursuit….”[vi]

Winchester’s war experiences continued, and the homefront tragedy grew darker each time their soldiers fought nearby.

Fine art gives Jackson and his army an organized hero’s welcome to Winchester, capturing the civilian enthusiasm of the scene. However, in reality the scenes on the streets would have much more chaotic, weary, hungry, un-posed, and a hurried dash as the Confederates raced through town in a semi-unsuccessful pursuit of their foes. The darker side of the history is also missing in the fine art — the dead sons who perished nearly at their home doorsteps, the struggle and fear of fleeing to find or keep freedom, and the loyalty crisis that continued to playout on the homefront between neighbors.

The “liberation” of Winchester can be seen as a moment that cements Jackson’s place in history, and artistic versions certainly support that concept. Though the Valley Campaign still had a couple more weeks, long marches, and two more battles, the recapture of Winchester took the imaginations of the Southerners and vindicated Jackson for the previous retreats and hardships he had forced on soldiers and civilians alike. Even if the scenes did not happen the way they have been remembered in art, the memory of May 25, 1862 in Winchester became a focal memory for Southern-supporting civilians in that town and region. They would spend the rest of the war hoping for a repeat of Jackson’s entry and every new Confederate commander in the Shenandoah Valley faced that memory of the exciting day when the majority of the diary keepers in Winchester felt free and liberated.

Was it really a liberation? In some perspectives and some contexts of the word, yes. But even as they celebrated a Confederate victory, chains of homefront division, lack of military pursuit, fears and actual bondage, and loss pulled at the scene. There are more sides to the history, even without adding Union military voices, and the liberation may not have been as glorious as civilian and soldiers would spend decades remembering.


Jonathan A. Noyalas, Plagued by War: Winchester, Virginia During the Civil War (Leesburg: Gauley Mountain Press, 2003).

Gary W. Gallagher, editor, The Shenandoah Valley Campaign of 1862 (Chapel Hill: University of North Carolina Press, 2003).

[i] Laura Lee/Julia Chase, edited by Michael G. Mahon, Winchester Divided: The Civil War Diaries of Julia Chase & Laura Lee (Mechanicsburg: Stackpole Books 2002). Page 40.

[ii] Ibid., Page 38.

[iii] Peter Cozzen, Shenandoah 1862: Stonewall Jackson’s Valley Campaign (Chapel Hill: University of North Carolina Press, 2008). Page 373.

[iv] Ibid., Page 377.

[v] David Hunter Strother, edited by Cecil D. Eby, Jr., A Virginia Yankee in the Civil War: The Diaries of David Hunter Strother (Chapel Hill: University of North Carolina Press, 1961). Page 43.

[vi][vi] Laura Lee/Julia Chase, edited by Michael G. Mahon, Winchester Divided: The Civil War Diaries of Julia Chase & Laura Lee (Mechanicsburg: Stackpole Books 2002). Page 41.

4 Responses to Liberating Winchester?

  1. This post provides a helpful reminder of the collateral damage that results from the battling armies. Not only citizens, but unfortunate enslaved families, suffered. Sarah makes it clear that these people were more than bystanders.

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