Prelude to the Battle
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 Rebel 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.
Stuart Establishes a New Line Near 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.
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.
Aftermath of the Battle
National Park Service historians estimate that casualties at the Battle of Upperville totaled 400 soldiers from both sides.