Upperville was a Civil War engagement fought in Virginia, 1863. The outcome was inconclusive.
On June 21, Union cavalry made a determined effort to pierce Stuart's cavalry screen. Hampton's and Robertson's brigades made a stand at Goose Creek, west of Middleburg, and beat back Gregg's division. Buford's column detoured to attack the Confederate left flank near Upperville but encountered William E. "Grumble" Jones's and John R. Chambliss's brigades while J.I. Gregg's and Kilpatrick's brigades advanced on the Upperville from the east along the Little River Turnpike. After furious mounted fighting, Stuart withdrew to take a strong defensive position in Ashby Gap, even as Confederate infantry crossed the Potomac into Maryland. As cavalry skirmishing diminished, Stuart made the fateful decision to strike east and make a circuit of the Union army as it marched toward Gettysburg.
On June 21, 1863, fighting broke out in Loudoun County, Virginia, near the town of Upperville, as part of the Gettysburg campaign during the American Civil War.
Union horsemen pushed hard in an attempt to break through the cavalry screen Maj. Gen. J.E.B. Stuart had thrown up for the Confederates. In the days before, Stuart had waged a string of delaying actions across the Loudoun Valley, trying to stop General Alfred Pleasonton's Union cavalry from learning where Lee's Army of Northern Virginia truly lay, since a large portion of that army sat in the Shenandoah Valley just to the west of tiny Upperville. Ravines, creeks, and stonewalls all worked in his favor as he pulled his men steadily westward, and he had already used the terrain to slow the Federals at Aldie and Middleburg. Near Upperville he mounted yet another stubborn defense, and this time he managed to keep the Federal horsemen out of the Shenandoah Valley altogether.
When darkness fell after the June 19 clash at Middleburg, a punishing rain moved through the Loudoun Valley overnight, finally breaking a drought that had lasted six weeks. Amid that downpour, Wade Hampton brought his Confederate cavalry brigade up to strengthen J.E.B. Stuart's force, taking a position close to Beverly Robertson's brigade along the Ashby's Gap Turnpike. Farther along, John R. Chambliss pushed his brigade north to link up with "Grumble" Jones near Unison, Virginia, while Thomas T. Munford's brigade held ground even farther north, watching over the approach to Snickersville Gap. Meanwhile, John Mosby's rangers kept watch on the Union forces, feeding back valuable information about their movements.
On the Union side, cavalry chief Alfred Pleasonton had grown weary of the skill with which Stuart's dismounted troopers used stone walls for cover, so on June 20 he called on Maj. Gen. George G. Meade for help, and the V Corps sent infantry to his aid. Lee's main army still eluded him, a failure the War Department kept pressing him to correct. In hopes of dislodging Stuart, Pleasonton pushed Judson Kilpatrick's brigade forward along the Ashby's Gap Turnpike, backed by Col. Strong Vincent's infantry brigade, while David McM. Gregg's cavalry division waited in reserve. John Buford's division was tasked with sweeping around the flank.
Stuart had hoped to let his exhausted men rest on the Sabbath, but that hope vanished when Union guns began firing on his lines around eight o'clock on the morning of June 21. His troops held off Kilpatrick's cavalry for a time, making skillful use of stone walls, ravines, and streams, but the pressure from Union infantry eventually forced a retreat. He rallied west of Rector's Crossroads at the stone bridge spanning Goose Creek, holding that line for two more hours against repeated assaults from mounted troopers and from the 16th Michigan Infantry, whose skirmishers and sharpshooters moved forward to target the Confederate cannoneers.
As Union soldiers pressed closer, the Confederate artillery crews scrambled to hitch their guns and pull back, but one Blakely rifle overturned while its crew tried to flee, and Federal troops seized it, marking the first time an artillery piece had been lost from Stuart's cavalry. Soon after, two of the three guns still with him broke down as well, and Stuart pulled back toward Upperville, continuing to fight delaying actions wherever the terrain allowed.
Buford's Union troops swung wide in an effort to strike the reconstituted Confederate left near Upperville, even as the brigades of J. Irvin Gregg and Judson Kilpatrick pushed in from the east on the Ashby's Gap Turnpike. It did not take long for Buford to run into "Grumble" Jones and Chambliss, whose Confederate brigades were guarding Stuart's supply train just to the north of town, and he launched an assault against them. At the same time, Kilpatrick's horsemen went after Hampton and Robertson atop a ridge east of Upperville called Vineyard Hill. A handful of the Union riders pushed all the way into the village itself before being driven back.
The mounted combat raged fiercely before Stuart pulled his men back to a strong position in Ashby's Gap, even as Confederate foot soldiers had already begun wading across the Potomac into Maryland. Over the following days the cavalry clashes tapered off, and Stuart then made the decision that would shape events to come: he chose to ride east and swing around the entire Union army during its march toward Gettysburg.
The fight at Upperville mattered because Stuart's skillful delaying actions kept Pleasonton from pinning down where Lee's infantry divisions actually were, denying the Federals critical knowledge of their opponent's location and intentions.
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