The Battle of Upperville, 1863

June 21, 1863

The Battle of Upperville was fought between the United States of America and the Confederate States of America on June 21, 1863. The outcome of the battle was inconclusive.

JEB Stuart, Civil War General

Confederate forces led by J. E. B. Stuart were able to take a strong defensive position at Ashby Gap, which helped keep Union forces from learning about the movements of General Lee’s Army of Northern Virginia. Image Source: New York Public Library Digital Collections.

Battle of Upperville Summary

The Battle of Upperville was fought on June 21, 1863. Union forces led by General Hugh Judson Kilpatrick and General John Buford clashed with Confederate forces under the command of General J.E.B. Stuart. Following the Battle of Middleburg, General Stuart established a defensive line near Upperville, Virginia. On June 20, both sides deployed troops in the area in preparation for battle. On the morning of the 21st, Kilpatrick’s cavalry attacked, followed by Buford’s cavalry. The Confederates were able to push the Federals back but were forced to continue moving west, away from Washington, D.C. However, Stuart was able to keep Union forces from pushing through and engaging Robert E. Lee’s army as he marched north, eventually leading to the Battle of Gettysburg.

General John Buford, Civil War
General John Buford (USA). Image Source: Library of Congress.

Battle of Upperville Facts

  • Date Started: The Battle of Upperville started on June 21, 1863.
  • Date Ended: The battle ended on June 21, 1863.
  • Location: The Battle of Upperville took place in Loudoun County, in and around Upperville, Virginia.
  • Campaign: The battle was part of the Gettysburg Campaign of 1863.
  • Who Won: The outcome of the battle is considered inconclusive.

Battle of Upperville History and Overview

Lee Heads North

In early May 1863, Confederate General Robert E. Lee and his Army of Northern Virginia soundly defeated Major General Joseph Hooker and his Army of the Potomac at the Battle of Chancellorsville. Despite the Confederate victory, Lee’s army needed food, horses, and equipment after the battle. With northern Virginia ravaged by two years of combat, Lee took the war to 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. Lee began consolidating his army near Culpeper, Virginia, and troop movements began on June 3, 1863.

Robert E Lee, 1864, Portrait
General Robert E. Lee (CSA). Image Source: Wikipedia.

Cavalry Engagement at Brandy Station

To mask his intentions and screen the assembly of his invasion force, Lee stationed his cavalry, commanded by Major General J. E. B. Stuart, at Brandy Station, a few miles northeast of Culpeper. 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, 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.

Second Battle of Winchester

After the Battle of Brandy Station, Lee’s army continued its trek northwest toward Winchester in the Shenandoah Valley where roughly 6,900 troops were garrisoned under the command of Brigadier General Robert Milroy. On June 13, Lieutenant General Richard Ewell and his 2nd Army Corps reached Winchester. Ewell initiated a three-day engagement known as the Second Battle of Winchester that forced Milroy’s evacuation, clearing the upper Shenandoah Valley for Lee’s advancement.

Stuart Screens Lee’s Movements

As Lee continued to move north on the west side of the Blue Ridge Mountains, he ordered Stuart’s Cavalry to move in the same direction through the Loudoun Valley on the east side of the mountains, screening the Confederate invasion force. Lee instructed Stuart to prevent Federal reconnaissance forces from advancing through gaps in the mountains to gather information about the Army of Northern Virginia’s movements. Part of Stuart’s orders included holding the Ashby’s Gap Turnpike and the Snickersville Turnpike, two strategic roads leading through the mountains.

Battle of Aldie

Frustrated by the lack of intelligence about Lee’s movements, on June 16, 1863, Hooker ordered Pleasonton, “to give him information of where the enemy is, his force, and his movements.” On June 17, Pleasonton ordered Major General David Gregg and his division to seize and occupy Aldie, where the two roads converged, setting the stage for a cavalry engagement that afternoon — The Battle of Aldie.

What Happened at the Battle of Upperville?

On the same day, Pleasonton determined to seize the hamlet of Middleburg about five miles west of Aldie, where Stuart had established his headquarters. A series of back-and-forth engagements over the next two days forced Stuart to withdraw about eight miles to the west and establish a new defensive line across the Ashby Gap Turnpike near the village of Upperville. Although Stuart had ceded Middleburg, his forces still blocked the Ashby Gap through the Blue Ridge Mountains, and Pleasonton knew no more about Lee’s movements than he did when the fighting began.

Pleasonton rested his troops during a daylong downpour on June 20, before renewing his efforts to penetrate Stuart’s cavalry screen. At Pleasonton’s request, Hooker deployed infantry units from Major General George Meade and his 5th Corps to support the Union cavalry.

Meanwhile, Stuart was gathering his cavalry near Upperville. He deployed brigades commanded by Brigadier General Wade Hampton and Brigadier General Beverly Robertson along the Ashby Gap Turnpike. He also moved Brigadier General John R. Chambliss’s brigade north of the turnpike where they joined Brigadier General William E. “Grumble” Jones’s brigade near Union, Virginia. Farther north, Colonel Thomas T. Munford’s brigade guarded access to the Snickersville Gap. Finally, Stuart assigned Major John Mosby’s rangers to scout Pleasonton’s movements.

Federals Attack at Upperville

The next morning, Sunday, June 21, on Pleasonton’s orders, Brigadier General Judson Kilpatrick’s cavalry brigade, supported by a brigade of infantry, assaulted Stuart’s troopers where the Ashby Gap Turnpike crosses Goose Creek. Stuart’s outnumbered force withstood the initial Federal surge, but gradually withdrew westward toward Upperville, using stone walls and deep ravines for cover.

Hugh Judson Kilpatrick, Civil War General
General H. Judson Kilpatrick (USA). Image Source: Wikipedia.

As Union forces continued to press the issue along the turnpike, Jones and Chambliss repulsed an effort by Brigadier General John Buford to turn Stuart’s left flank. Following pitched fighting on two fronts, Stuart withdrew once again, taking up a stronger defensive position at the Ashby Gap through the Blue Ridge Mountains.

Battle of Upperville Outcome

Pleasonton chose not to press the issue and returned to Aldie. Once again, Stuart’s strategy of giving up ground to buy time-deprived Pleasonton of vital information about Lee’s movements, which he was desperately seeking.

National Park Service historians estimate that casualties at the Battle of Upperville totaled 400 soldiers from both sides.

Battle of Upperville Significance

The Battle of Upperville was important because Union forces were unable to move past Confederate Cavalry to gather information about the movement of the Confederate Army.

Battle of Upperville Casualties, Generals, and Participants

Principal Union Commanders

Principal Confederate Commanders

  • Major General J.E.B. Stuart
  • Brigadier General Wade Hampton
  • Brigadier General Beverly Robertson
  • Brigadier General John R. Chambliss
  • Brigadier General William E. “Grumble” Jones
  • Colonel Thomas T. Munford
  • Major John Mosby

Union Forces Engaged

  • Various cavalry regiments and one infantry brigade (Army of the Potomac)

Confederate Forces Engaged

  • Various cavalry regiments (Army of Northern Virginia)

Number of Union Soldiers Engaged

  • Undetermined

Number of Confederate Soldiers Engaged

  • Undetermined

Estimated Casualties

  • Combined casualties were roughly 400 (killed, wounded, captured/missing)


  • Inconclusive

Battle of Upperville Dates and Timeline

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

Battle of Upperville 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.

Small but Important Riots: The Cavalry Battles of Aldie, Middleburg, and Upperville by Robert F. O’Neill

This book is a tactical study of fighting from June 17 to 22, 1863, at Aldie, Middleburg, and Upperville, placed within the strategic context of the Gettysburg Campaign. It is based on Robert O’Neill’s 30 years of research and access to previously unpublished documents, which reveal startling new information. Since the fighting in Loudoun Valley of Virginia ended in June 1863, one perspective has prevailed — that Brigadier General Alfred Pleasonton, who commanded the Cavalry Corps, Army of the Potomac, disobeyed orders. According to published records, Pleasonton’s superiors, including President Abraham Lincoln, Secretary of War Edwin Stanton, and army commander Joseph Hooker, ordered Pleasonton to search for General Robert E. Lee’s Army of Northern Virginia during a critical stage of the Gettysburg Campaign, and Pleasonton ignored their orders. Recently discovered documents — discussed in this book — prove otherwise.

Citation Information

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  • Article Title The Battle of Upperville, 1863
  • Date June 21, 1863
  • Author
  • Keywords Battle of Upperville, Gettysburg Campaign, Robert E. Lee
  • Website Name American History Central
  • Access Date July 20, 2024
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 17, 2024