Overview
In early May 1863, Confederate General Robert E. Lee and the Army of Northern Virginia defeated General Joseph Hooker and the Army of the Potomac at the Battle of Chancellorsville. Lee then decided to move north because two years of fighting had devastated northern Virginia, and his army needed food, horses, equipment, and other supplies. On June 3, Lee’s troops started moving northwest toward the Shenandoah Valley and eventually Maryland and Pennsylvania.
Lee ordered General J.E.B. Stuart and his cavalry to protect the army’s movements. On June 9, Union cavalry under General Alfred Pleasonton attacked Stuart at the Battle of Brandy Station. Pleasonton withdrew without discovering Lee’s main camp. Confederate forces later cleared the upper Shenandoah Valley at the Second Battle of Winchester.
As Lee continued northwest of the Blue Ridge Mountains, Stuart moved through the Loudoun Valley on the eastern side. His cavalry guarded important mountain passes and prevented Union reconnaissance forces from learning Lee’s location and movements.
On June 17, Union and Confederate cavalry fought at Aldie and Middleburg. Fighting near Middleburg forced Stuart to withdraw west and establish another defensive line near Upperville. Although Stuart gave up ground, his cavalry continued to block Ashby Gap.
After resting during heavy rain on June 20, Pleasonton renewed his advance the next morning. General Hugh Judson Kilpatrick’s cavalry, supported by infantry, attacked Stuart’s troops at Goose Creek. The Confederates resisted, then withdrew toward Upperville. General John Buford also tried to turn Stuart’s left flank, but Confederate forces under William E. “Grumble” Jones and John R. Chambliss stopped his attack.
Stuart eventually withdrew to a stronger position at Ashby Gap. Pleasonton chose not to continue the attack and returned to Aldie. Although the battle was inconclusive, Stuart accomplished his main objective by preventing Union forces from breaking through his cavalry screen and discovering Lee’s movements.
Essential Facts
- Date: June 21, 1863.
- Location: Upperville and surrounding areas in Loudoun County, Virginia.
- Participants: The United States of America (USA) and the Confederate States of America (CSA).
- USA Commanders: Alfred Pleasonton, Hugh Judson Kilpatrick, and John Buford.
- CSA Commanders: J.E.B. Stuart, Wade Hampton, Beverly Robertson, John R. Chambliss, William E. “Grumble” Jones, Thomas T. Munford, and John Mosby.
- Who Won: The outcome of the Battle of Upperville was inconclusive.
- Campaign: Gettysburg Campaign.
- Era: Civil War, July–December, 1863.
Statistics
United States of America
- Casualties: Undetermined.
- Forces Engaged: Various cavalry regiments and one infantry brigade from the Army of the Potomac.
- Troop Strength: Undetermined.
Confederate States of America
- Casualties: Undetermined.
- CA Forces Engaged: Various cavalry regiments from the Army of Northern Virginia.
- Troop Strength: Undetermined.
Significance
The Battle of Upperville is important to American History because the outcome helped protect the movements of Robert E. Lee’s Army of Northern Virginia during the Gettysburg Campaign. Union cavalry tried to break through J.E.B. Stuart’s defensive screen to discover where Lee’s army was moving. Although Stuart repeatedly gave up ground and withdrew west, his forces stopped Hugh Judson Kilpatrick’s advance and prevented John Buford from turning the Confederate left flank. Stuart accomplished his main objective of keeping Lee’s movements hidden as the Confederate army continued toward Maryland and Pennsylvania.
History
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.
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.
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.
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.
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.
Outcome
Pleasonton chose not to press the issue and returned to Aldie. Once again, Stuart’s strategy was to give up ground to buy time-deprived Pleasonton 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.
Timeline
- 1863, April 30–May 6 — Robert E. Lee and the Army of Northern Virginia defeated Joseph Hooker and the Army of the Potomac at the Battle of Chancellorsville.
- 1863, June 3 — Confederate troop movements started as Lee gathered his army near Culpeper, Virginia, for his invasion of the North.
- 1863, June 5 — Confederate forces won the Battle of Franklin’s Crossing.
- 1863, June 9 — Union and Confederate forces fought the inconclusive Battle of Brandy Station.
- 1863, June 13–15 — The Confederates won the Second Battle of Winchester.
- 1863, June 17 — Union and Confederate forces fought the inconclusive Battle of Aldie.
- 1863, June 17–19 — Union and Confederate forces fought the inconclusive Battle of Middleburg.
- 1863, June 20
- Alfred Pleasonton rested his troops during heavy rain while Stuart gathered and positioned his cavalry near Upperville.
- Hugh Judson Kilpatrick attacked Stuart’s forces at Goose Creek.
- John Buford tried to turn Stuart’s left flank, but Confederate forces stopped the attack.
- Stuart withdrew toward Ashby Gap, and Pleasonton eventually returned to Aldie.
AP US History
Definition
Battle of Upperville (1863) — The Battle of Upperville was fought on June 21, 1863, during the Gettysburg Campaign. Union cavalry under Hugh Judson Kilpatrick attacked J.E.B. Stuart’s forces at Goose Creek, while John Buford tried to turn the Confederate left flank. Stuart gradually withdrew toward Upperville and later Ashby Gap. Although Confederate forces gave up ground, they prevented Union troops from breaking through and gathering information about Robert E. Lee’s movements.
Alignment
The Battle of Upperville is part of the following AP US History sections:
Suggested Reading
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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.
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.
