Overview
The Battle of Middleburg took place from June 17–19, 1863, as Confederate General Robert E. Lee moved the Army of Northern Virginia north during the Gettysburg Campaign. After defeating the Union Army of the Potomac at the Battle of Chancellorsville, Lee moved his army toward the Shenandoah Valley and prepared to enter Maryland and Pennsylvania. General J.E.B. Stuart’s Confederate cavalry protected Lee’s movements on the eastern side of the Blue Ridge Mountains.
Union General Alfred Pleasonton tried to determine Lee’s location and movements. On June 17, Pleasonton ordered General David Gregg to occupy Aldie. That same day, he ordered Colonel Alfred Duffié and the 1st Rhode Island Cavalry to capture Middleburg, about five miles west of Aldie.
Duffié easily entered the lightly defended village and nearly captured Stuart, who was eating lunch when the Union cavalry arrived. However, Duffié remained isolated in Middleburg. Confederate cavalry returned that evening and surrounded his command. The next morning, Duffié ordered his men to fight their way through the Confederate lines. Duffié and about 50 men escaped, but most of his command was killed, wounded, missing, or captured.
On June 19, Gregg’s cavalry recaptured Middleburg and drove the Confederates west along the Ashby Gap Turnpike. Stuart established a strong defensive line about one mile west of town at Mount Defiance. Union forces repeatedly attacked the position but failed to break the Confederate line. One Union charge nearly captured Confederate artillery before a Confederate counterattack drove the Federals back.
As more Union cavalry arrived, Stuart withdrew west toward Upperville and established another defensive position. Although the Federals controlled Middleburg, Stuart continued to block their route through the Blue Ridge Mountains. Pleasonton and General Joseph Hooker gained little additional information about Lee’s movements. The fighting set the stage for the Battle of Upperville on June 21.
Essential Facts
- Date: June 17–19, 1863.
- Location: Middleburg, Loudoun County, Virginia.
- Participants: The United States of America (USA) and the Confederate States of America (CSA).
- USA Commanders: David M. Gregg, Alfred Duffié, John Irvin Gregg.
- CSA Commanders: J.E.B. Stuart.
- Who Won: The outcome of the Battle of Middleburg was inconclusive.
- Campaign: Gettysburg Campaign.
- Era: Civil War, July–December, 1863.
Statistics
United States of America
- Casualties: 349 killed, wounded, captured, or missing.
- Forces Engaged: Various cavalry regiments of the Army of the Potomac.
- Troop Strength: Undetermined.
Confederate States of America
- Casualties: Approximately 40 killed, wounded, captured, or missing.
- Forces Engaged: Various cavalry regiments of the Army of Northern Virginia.
- Troop Strength: Undetermined.
Significance
The Battle of Middleburg is important to American History because it formed part of the cavalry fighting that accompanied General Robert E. Lee’s advance north during the Gettysburg Campaign. Union cavalry nearly captured General J.E.B. Stuart on June 17, but Confederate forces later surrounded Colonel Alfred Duffié’s command and captured many of his soldiers. Although General David Gregg’s cavalry recaptured Middleburg on June 19 and forced Stuart to withdraw toward Upperville, the Confederates continued to block Union access through the Blue Ridge Mountains. As a result, Generals Alfred Pleasonton and Joseph Hooker still had little information about Lee’s movements when the fighting ended.
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 gathering 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.
Confederates Return to 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.
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.
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.
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
- Pleasonton ordered General David Gregg to seize Aldie and Colonel Alfred Duffié to capture Middleburg.
- Union and Confederate forces fought the inconclusive Battle of Aldie.
- Duffié’s cavalry captured Middleburg and nearly captured Stuart.
- Confederate cavalry returned to Middleburg and surrounded Duffié’s command that evening.
- 1863, June 18 — Duffié ordered his men to fight their way through the Confederate lines, but most of his command was killed, wounded, missing, or captured.
- 1863, June 19
- Gregg’s cavalry recaptured Middleburg and drove Confederate forces west toward Mount Defiance.
- Union forces repeatedly attacked Stuart’s defensive position at Mount Defiance but failed to break the Confederate line.
- Stuart withdrew west toward Upperville as additional Union cavalry arrived.
AP US History
Definition
Battle of Middleburg (1863) — The Battle of Middleburg was a cavalry engagement fought from June 17–19, 1863, during the Gettysburg Campaign. Colonel Alfred Duffié captured Middleburg and nearly captured Confederate General J.E.B. Stuart, but Confederate forces surrounded Duffié’s command and captured many of his men. General David McMurtrie Gregg later recaptured the town and attacked Stuart’s defensive position at Mount Defiance. As Union reinforcements arrived, Stuart withdrew toward Upperville while continuing to block Federal scouting efforts.
Alignment
The Battle of Middleburg is part of the following AP US History sections:
Suggested Reading
Please note that this section contains affiliate links to Amazon.com. If you click the links and purchase anything, American History Central may earn a commission.
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.
