The Battle of Middleburg took place from June 17 through June 19, 1863, during Robert E. Lee's Gettysburg Campaign.
In early May 1863, Confederate General Robert E. Lee’s Army of Northern Virginia soundly defeated Major General Joseph Hooker’s Army of the Potomac at the Battle of Chancellorsville. Despite the Rebel victory, Lee’s army was in need of food, horses, and equipment after the battle. With northern Virginia ravaged by two years of combat, Lee decided to take 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.
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’s Cavalry Corps launched a surprise attack against Stuart’s Cavalry Division near Brandy Station. After an all-day fight, Pleasonton retired without discovering Lee’s main encampment at Culpeper, only six miles away.
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’s 2nd Army Corps reached Winchester and initiated a three-day engagement that forced Milroy’s evacuation, clearing the upper Shenandoah Valley for Lee’s advancement.
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.
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’s division to seize and occupy Aldie, where the two roads converged, setting the stage for a cavalry engagement that afternoon.
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 Yankees 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 Rebel 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.
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 Rebel artillery near the summit, but a spirited Confederate counterattack drove the Yankees back.
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 ridge line near the town of Upperville. 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.