The Second Battle of Winchester — The Confederate Victory that Opened the Road to Gettysburg

June 13–15, 1863

The Second Battle of Winchester was fought between the United States of America and the Confederate States of America from June 13–15, 1863. The outcome of the battle was a Confederate victory and cleared the Upper Shenandoah Valley of Union resistance, paving the way for Robert E. Lee’s Second Invasion of the North.

Richard Ewell, Civil War General

Lieutenant General Richard Ewell’s victory at the Second Battle of Winchester cleared the upper Shenandoah Valley of Union resistance, paving the way for Confederate General Robert E. Lee’s invasion of Maryland and Pennsylvania. Image Source: New York Public Library Digital Collections.

Second Battle of Winchester Summary

The Second Battle of Winchester was fought from June 13–15, 1863. Confederate forces led by General Richard Ewell clashed with Union forces led by General Robert Milroy near Winchester, Virginia. Skirmishes broke out on June 13, as Confederate forces closed in on the town, where Union forces gathered in an isolated fort. On the 14th, Ewell’s men overwhelmed the fort and cut off Milroy’s escape route. The next day, Milroy was unable to break through Ewell’s lines and was forced to surrender. Ewell’s victory cleared the way for General Robert E. Lee to continue moving north toward Maryland and Pennsylvania, eventually leading to the Battle of Gettysburg.

General Robert H. Milroy, Civil War, USA
General Robert H. Milroy (USA). Image Source: Library of Congress.

Second Battle of Winchester Facts

  • Date Started: The Second Battle of Winchester started on June 13, 1863.
  • Date Ended: The battle ended on June 15, 1863.
  • Location: The Second Battle of Winchester took place in Frederick County, near Winchester, Virginia.
  • Campaign: The battle was part of the Gettysburg Campaign of 1863.
  • Who Won: The Confederate States of America won the Second Battle of Winchester.

Second Battle of Winchester History and Overview

Lee Heads North

After the decisive Confederate victory at the Battle of Chancellorsville (April 30–May 6, 1863) Robert E. Lee began preparing for his Second Invasion of the North. Lee planned to disengage from Union forces near Fredericksburg, move the Army of Northern Virginia northwest across the Blue Ridge Mountains, and then push northeast through the Shenandoah Valley into Maryland and Pennsylvania.

Troop movements began on June 3, 1863. By June 5, Lee’s 1st Army Corps, commanded by Lieutenant General James Longstreet and his 2nd Army Corps, commanded by Lieutenant General Richard Ewell, had traveled about forty miles and encamped near Culpeper, Virginia.

Battle of Brandy Station

Also operating in the vicinity was Major General J. E. B. Stuart and his Cavalry Division. On June 9, Union Major General Alfred Pleasonton and his Cavalry Corps launched a surprise attack against Stuart’s Cavalry Division near Brandy Station. After an all-day fight at the Battle of Brandy Station, Pleasonton retired without discovering Lee’s main encampment at Culpeper, which was only six miles away.

Battle of Brandy Station, 1863, Cavalry Charge, LOC
This illustration depicts a cavalry charge at the Battle of Brandy Station. Image Source: Library of Congress.

What Happened at the Second Battle of Winchester?

After the Battle of Brandy Station, Lee’s army continued their trek northwest toward Winchester in the Shenandoah Valley where roughly 6,900 Federal troops had garrisoned under the command of Brigadier General Robert Milroy. As Ewell approached Winchester, he divided his 19,000-man 2nd Corps into two wings.

June 13 — Skirmishing Erupts Near Winchester

Skirmishing erupted on June 13, as Confederate Major General Edward “Allegheny” Johnson’s Division approached Winchester from the southeast and Confederate Major General Jubal Early and his Division approached from the southwest. Unaware that he was facing Ewell’s entire corps, Milroy began concentrating his forces at Winchester, despite instructions from Washington to evacuate and fall back to Harpers Ferry.

General Edward Allegheny Johnson, Civil War
General Edward “Allegheny” Johnson (CSA). Image Source: Museum of the Confederacy.

June 14 — Confederate Successes

Confederates Overrun Federal Fort

Skirmishing continued on June 14 as Ewell’s soldiers began closing in on Milroy’s isolated garrison. Throughout the day, Ewell established artillery positions on the high ground west of town and he began bombarding the Federal defenders during the late afternoon. The Confederates then overran Milroy’s small fort and batteries guarding the west side of town.

Milroy Tries to Evacuate

By 9 p.m., Milroy, now aware of what he was up against, called a council of war with his officers and decided to evacuate his men via the Martinsburg Turnpike which ran northeast out of town. Aware of Milroy’s predicament, Ewell sent Johnson’s division on a night flanking march to cut off the Federal avenue of retreat.

June 15 — Federal Surrender

At about 4 a.m. on June 15, the lead elements of Milroy’s retreating garrison encountered skirmishers from Johnson’s Corps roughly five miles north of Winchester, near Stephenson’s Depot.  Johnson quickly formed battle lines to block his adversary’s retreat. The now-desperate Milroy launched three unsuccessful assaults attempting to break through the Confederate lines and escape. When the Stonewall Brigade reinforced Johnson, he launched a counterattack and Federal troops began surrendering. Escorted by a few hundred cavalrymen Milroy escaped from the battlefield and eluded the Confederate troops who pursued him.

Second Battle of Winchester Outcome

Union losses at the Second Battle of Winchester were significant. In Ewell’s official report, he claimed to capture “23 pieces of artillery (nearly all rifled), 4,000 prisoners, 300 loaded wagons, over 300 horses, and quite a large amount of commissary and quartermaster’s stores.” The Union lost an additional 95 men killed and over 300 wounded. Ewell’s losses totaled 269 (47 killed, 219 wounded, and 3 missing).

Ewell’s victory cleared the upper Shenandoah Valley of Union resistance, paving the way for Lee’s invasion of Maryland and Pennsylvania. It also enhanced Ewell’s reputation in his first test as a corps commander following the death of Thomas “Stonewall” Jackson at the Battle of Chancellorsville.

Milroy, on the other hand, was disgraced. His defeat was so great that his command nearly ceased to exist following the battle. On June 27, Union General-in-Chief Henry Halleck ordered Milroy’s arrest. In August, President Lincoln authorized the military to convene a court of inquiry to determine Milroy’s culpability at Winchester. After several months of testimony and deliberation, the court of inquiry exonerated Milroy. Despite Milroy’s many requests during the next year, he did not command men in battle again until December 1864.

Second Battle of Winchester Significance

  • The decisive action during the Second Battle of Winchester took place on June 15, 1863, near Stephenson’s Depot, roughly five miles northeast of Winchester, Virginia.
  • Confederate forces captured 23 pieces of artillery, 300 loaded wagons, more than 300 horses, and quite a large amount of commissary and quartermaster’s stores at the Second Battle of Winchester.
  • The Confederate victory at the Second Battle of Winchester cleared the upper Shenandoah Valley of Union resistance, paving the way for Robert E. Lee’s invasion of Maryland and Pennsylvania.
  • Ewell’s victory at the Second Battle of Winchester enhanced his reputation in his first test as a corps commander following the death of Thomas “Stonewall” Jackson at the Battle of Chancellorsville.
  • Following his defeat at the Second Battle of Winchester, Union commander Robert Milroy was arrested and later tried and acquitted by a Union military court of inquiry.
  • Following his defeat at the Second Battle of Winchester, Union commander Robert Milroy did not command men in battle again until December 1864.

Second Battle of Winchester, Casualties, Generals, and Participants

Principal Union Commanders

  • Brigadier General Robert Milroy

Principal Confederate Commanders

  • Lieutenant General Richard Ewell

Union Forces Engaged

  • 2nd Division, 8th Corps, Middle Department, garrisoned at Winchester

Confederate Forces Engaged

  • 2nd Corps (Army of Northern Virginia)

Number of Union Soldiers Engaged

  • Roughly 6,900

Number of Confederate Soldiers Engaged

  • Roughly 19,000

Union Casualties

  • 3,000-4,000+ (95 killed, over 300 wounded, 3,000 to 4,000 captured/missing)

Confederate Casualties

  • 269 (47 killed, over 219 wounded, 3 missing)

Result

  • Confederate victory

Second Battle of Winchester Dates and Timeline

These are the main battles and events of the Gettysburg Campaign in order.

Second Battle of Winchester Suggested Reading

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“If We Are Striking for Pennsylvania”: The Army of Northern Virginia and the Army of the Potomac March to Gettysburg. Volume 1: June 3–21, 1863 by Scott L. Mingus Sr. and Eric J. Wittenberg

“If We Are Striking for Pennsylvania”: The Army of Northern Virginia and the Army of the Potomac March to Gettysburg. Volume 2: June 22–30, 1863

Mingus and Wittenberg, the authors of more than 40 Civil War books, present a history of the opening moves of the Gettysburg Campaign in the 2-volume study. This compelling study is one of the first to integrate the military, media, political, social, economic, and civilian perspectives with rank-and-file accounts from the soldiers of both armies as they inexorably march toward their destiny at Gettysburg. This first volume covers June 3–21, 1863, while the second, covers June 22–30, completes the march, and carries the armies to the eve of the Battle of Gettysburg.

The Second Battle of Winchester: The Confederate Victory that Opened the Door to Gettysburg by Eric J. Wittenberg and Scott L. Mingus Sr.

Historians Eric J. Wittenberg and Scott L. Mingus Sr. combine their talents to produce the most in-depth and comprehensive study of the Second Battle of Winchester ever written. Their balanced effort, based upon scores of archival and previously unpublished diaries, newspaper accounts, letter collections, other firsthand sources, and a deep familiarity with the terrain in and around Winchester and the lower Shenandoah Valley, explores the battle from every perspective.

Citation Information

The following information is provided for citations, including APA Style, Chicago Style, and MLA Style.

  • Article Title The Second Battle of Winchester — The Confederate Victory that Opened the Road to Gettysburg
  • Date June 13–15, 1863
  • Author
  • Keywords Second Battle of Winchester, Gettysburg Campaign, Civil War
  • Website Name American History Central
  • Access Date June 14, 2024
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 17, 2024

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