The Battle of Middleburg, 1863

June 17–June 19, 1863

The Battle of Middleburg was fought between the United States of America and the Confederate States of America from June 17–19, 1863. The outcome of the battle was inconclusive, however, Union forces nearly captured Confederate General J.E.B. Stuart on the first day of the battle.

JEB Stuart, Civil War General

Federal troops nearly captured Confederate Major General J. E. B. Stuart on the first day of the Battle of Middleburg. Image Source: New York Public Library Digital Collections.

Battle of Middleburg Summary

The Battle of Middleburg was fought from June 17–19, 1863. Union Cavalry led by Colonel Alfred Duffié and General David McMurtrie Gregg engaged Confederate Cavalry commanded by General J.E.B. Stuart. On the 17th, General Alfred Pleasonton ordered Duffié to capture the town of Middleburg, roughly 45 miles west of Washington, D.C. Duffié and his men were successful and nearly captured General Stuart, who was having lunch when Union forces arrived. That night, Confederate forces surrounded Duffié and his men, forcing them to try to fight their way out of the town the next morning. Duffié’s men suffered heavy casualties and many were captured. On the 19th, General Gregg’s cavalry attacked the town, successfully pushing the Confederates to the west where they formed a defensive line. Intense fighting continued for the rest of the day until Union reinforcements arrived. General Stuart withdrew to Upperville, setting the stage for the Battle of Upperville on June 21.

General Alfred Pleasonton, USA, Civil War
General Alfred Pleasonton (USA). Image Source: Library of Congress.

Battle of Middleburg Facts

  • Date Started: The Battle of Middleburg started on June 17, 1863.
  • Date Ended: The battle ended on June 19, 1863.
  • Location: The Battle of Middleburg took place in Loudoun County, in and around Middleburg, Virginia.
  • Campaign: The battle was part of the Gettysburg Campaign of 1863.
  • Who Won: The outcome of the battle is considered inconclusive.

Battle of Middleburg 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 gathering 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 Middleburg?

On the same day, Pleasonton also ordered Colonel Alfred Duffié’s 1st Rhode Island Cavalry to seize the hamlet of Middleburg about five miles west of Aldie. Duffié’s troopers easily took control of the lightly guarded village and nearly captured Stuart who was having a leisurely lunch when the Federals arrived. Despite being isolated, Duffié stubbornly followed his orders to hold Middleburg.

Confederates Return to Middleburg

As evening approached, Confederate troopers returned and surrounded the Rhode Islanders overnight. Realizing his precarious situation, the next morning Duffié ordered his men to try to break out of the Confederate trap. In the melee that followed, Duffié and roughly 50 of his troopers escaped. Of the 280 Union soldiers who occupied Middleburg the day before, six were killed, nine were wounded, and 210 were missing or captured.

Federals Recapture Middleburg

On June 19th, Gregg’s cavalry brigade recaptured Middleburg, driving the Confederate defenders out of town to the west along the Ashby Gap Turnpike.  About one mile west of town, Stuart’s troopers established a strong defensive line on a high piece of ground known as Mount Defiance. Repeated Union attacks on the Confederate position throughout the day proved fruitless. A tenacious charge nearly led to the capture of the Confederate artillery near the summit, but a spirited Confederate counterattack drove the Federals back.

Stuart Withdraws from Middleburg

As the day progressed, more Federal troopers arrived on the scene. Facing the possibility of being overwhelmed, Stuart withdrew his force to the west and positioned them along another ridgeline near the town of Upperville.

Battle of Middleburg Outcome

Despite the fact that Stuart retreated, he accomplished his overall mission. The Federals regained control of Middleburg, but Stuart’s forces at Upperville still blocked their path through the Blue Ridge Mountains. By the end of the fighting, Pleasonton and Hooker knew no more about Lee’s movements than they did when the fighting began.

Union losses at the Battle of Middleburg were 349. The Confederacy lost roughly 40 soldiers.

Battle of Middleburg Significance

  • Federal troops nearly captured Confederate Major General J. E. B. Stuart on the first day of the Battle of Middleburg

Battle of Middleburg Casualties, Generals, and Participants

Principal Union Commanders

  • Brigadier General David M. Gregg
  • Colonel Alfred Duffié
  • Colonel John Irvin Gregg

Principal Confederate Commanders

Union Forces Engaged

  • Various cavalry regiments of the Army of the Potomac

Confederate Forces Engaged

  • Various cavalry regiments of the Army of Northern Virginia

Number of Union Soldiers Engaged

  • Undetermined

Number of Confederate Soldiers Engaged

  • Undetermined

Union Casualties

  • 349 (killed, wounded, captured/missing)

Confederate Casualties

  • 40 (killed, wounded, captured/missing)


  • Inconclusive

Battle of Middleburg Dates and Timeline

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

Battle of Middleburg 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 Middleburg, 1863
  • Date June 17–June 19, 1863
  • Author
  • Keywords Battle of Middleburg, Gettysburg Campaign, Civil War
  • Website Name American History Central
  • Access Date July 15, 2024
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 17, 2024