Black and white photograph of Stonewall Jackson.

The Confederate victory at the First Battle of Winchester prompted President Lincoln to devise a complicated plan to stop Major General Thomas J. “Stonewall” Jackson, which eventually led to future Union defeats in the Shenandoah Valley and diverted more troops away from the Peninsula Campaign against Richmond. [Wikimedia Commons]

First Battle of Winchester

May 25, 1862

Fought on May 25, 1862, the First Battle of Winchester was the fourth engagement and third Confederate victory of the Shenandoah Valley Campaign of 1862.

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Prelude to the Battle

In the spring of 1862, Major General George B. McClellan was preparing to launch his much-anticipated Peninsula Campaign against the Confederate capital at Richmond, Virginia. Besides McClellan’s primary command, three Union forces to the northwest prepared to move south through the Shenandoah Valley to support the invasion.

Rebel Opponents

Opposing the three federal armies was a small Confederate force commanded by General Thomas “Stonewall” Jackson. Comprising the left wing of General Joseph Johnston’s Confederate Army of the Potomac (soon to become the famed Army of Northern Virginia), Jackson reported the size of his command as 4,297 infantry, 369 artillery, and 601 cavalry. As the Peninsula Campaign began, Johnston ordered Jackson to prevent the federal armies in the Shenandoah area from reinforcing McClellan.

Shenandoah Valley Campaign of 1862 Begins

The Shenandoah Valley Campaign of 1862 began on February 27, when Major General Nathaniel Banks, Union commander of the Department of the Shenandoah, led much of the 5th Corps of the Army of the Potomac (over 20,000 soldiers) across the Potomac River near Harpers Ferry and into Virginia. Banks’ aim was to move south, up the Shenandoah Valley, toward Richmond, to support McClellan’s offensive.

First Battle of Kernstown

On March 21, Jackson received faulty information that Banks had divided his force, leaving roughly 3,000 men, commanded by Brigadier General James Shields, at Winchester. Supposedly, Banks was marching the rest of his men back across the Potomac River to reinforce McClellan. Mindful of General Johnston’s directive to keep Banks in the Valley and to get as “near as prudence will permit,” Jackson ordered two grueling forced marches toward Winchester beginning on March 22.

On March 23, his 3,400-man division engaged Shields at Kernstown, just south of Winchester. Jackson discovered that Shields’s 3,000 Federals were in fact 8,500 strong. Shields was wounded during the First Battle of Kernstown, but his subordinate, Colonel Nathan Kimball, led the Yankees to victory, sending Jackson reeling back up the Valley (southward).

Battle of McDowell

On May 8, Jackson defeated two brigades of Major General John C. Frémont’s Mountain Department at the Battle of McDowell in the upper portions of the valley. Jackson’s victory at McDowell enabled him to turn his undivided attention to Banks’s army, which had moved south through the Shenandoah Valley to the vicinity of Strasburg.

As Jackson headed down the Shenandoah Valley (northward), he reunited with Richard Ewell’s division, which had been keeping tabs on Banks while Jackson was disposing of Frémont. The addition of Ewell’s division swelled the size of Jackson’s army to 17,000 men.

Battle of Front Royal

By May 22, Jackson had marched his soldiers to within ten miles of a Union garrison of roughly 1,000 men protecting Banks’ supply line at the village of Front Royal. On the next day, Jackson’s soldiers overwhelmed Colonel J.R. Kenly’s small command at the Battle of Front Royal and threatened to isolate or to flank Banks’ main army at Strasburg, thus forcing the Union general to retreat north toward the town of Winchester.

Commissary Banks

As Banks’s army withdrew down the Shenandoah Valley, Jackson’s troops harassed them throughout the day of May 24. During the retreat, the Rebels captured so many Union supplies that they later referred to the Federal commander as “Commissary Banks.”

Banks Stops at Winchester

As night approached, Banks stopped at Winchester, where the Valley Turnpike and the Front Royal Pike converged. Banks then deployed his force in a defensive formation south of town. He positioned Colonel George Henry Gordon’s brigade atop Bowers Hill on the west side of the Valley Turnpike, Brigadier-General John P. Hatch’s cavalry brigade on Camp Hill east of the Front Royal Pike, and Colonel Dudley Donnelly’s brigade southeast of Camp Hill to cover the Front Royal Pike.

May 25, 1862 — Clash at Winchester

Jackson allowed his troops only a few hours of rest before approaching Winchester. Before dawn on May 25, Ewell’s division advanced up the Front Royal Pike and then attacked Donnelly’s brigade from the southeast. When Ewell’s forces encountered heavy fire, he brought up his artillery and drove Donnelly’s men back toward Camp Hill.

Meanwhile, Jackson moved up the Valley Pike to assault Gordon’s brigade atop Bowers Hill from the south. Initially, the action developed into an artillery duel, but Gordon’s right flank eventually collapsed following a furious Rebel infantry attack.

Federals Retreat

Flanked on both sides, the Union center soon disintegrated, and Banks’ men fled through the streets of Winchester to escape Jackson’s surge forward. Civilians hurled insults and fired on the Bluecoats from buildings as they retreated through the town, adding to the chaos. Jackson’s cavalry became disorganized during the battle, and his infantry was too spent from the hard pursuit of the past few days to keep up with the fleeing Yankees. Jackson halted the pursuit almost five miles north of Winchester, enabling Banks to withdraw the rest of his army into Maryland.

Aftermath of the Battle

Although Banks escaped, the conflict cost him nearly one-third of his army. Union casualties at the First Battle of Winchester included roughly 2,000 soldiers (sixty-two killed, 243 wounded, and 1,714 missing/captured). The Confederacy lost only 400 men (sixty-eight killed, 329 wounded, and three missing).

Importance of the Battle

Jackson’s victory created a great deal of angst in Washington, especially with President Lincoln. Weary of Federal defeats in the Shenandoah Valley, Lincoln devised his own complicated plan to stop Jackson’s escapades. The president’s plan eventually led to future Union defeats in the Shenandoah Valley and diverted even more troops away from the campaign against Richmond.

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Citation Information

The following information is provided for citations.

  • Article Title First Battle of Winchester
  • Coverage May 25, 1862
  • Author
  • Keywords First Battle of Winchester
  • Website Name American History Central
  • Access Date July 31, 2021
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 6, 2021
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