Battle of Upperville: Stuart Holds the Gap

On June twenty-first, eighteen sixty-three, the cavalry battle that had been rolling westward through Loudoun County for five days reached its climax at the village of Upperville, six miles west of Middleburg and four miles short of Ashby's Gap in the Blue Ridge.

General Alfred Pleasonton's Union cavalry, reinforced by one brigade of infantry, pressed hard against J.E.B. Stuart's Confederate horse, pushing them through Middleburg and back to the ridge line above Upperville. The Union force numbered roughly ten thousand men and was the most concentrated Federal cavalry effort of the early war period. Stuart commanded perhaps seven thousand and was fighting a deliberate delaying action, every mile of ground he gave up being sold at the cost of Union time and information.

The fighting at Upperville on June twenty-first was the sharpest single engagement of the entire screening campaign. Union cavalry under General John Buford charged repeatedly toward the stone-walled lanes leading into the village. Stuart's men, including Wade Hampton's brigade and Beverly Robertson's brigade, used the terrain skillfully, falling back through farm lanes and over stone fences before making stands on successive ridge lines. The Confederate artillery, positioned on high ground south of the village, checked several Union advances.

By late afternoon Stuart had been pushed entirely through Upperville and back to the mouth of Ashby's Gap itself. There he stopped. Union cavalry could not force the gap in the face of dismounted Confederate fire and the rugged terrain. Pleasonton called off the assault.

Stuart had done what Lee required of him. For five days, from Aldie to Middleburg to Upperville, Federal cavalry had fought westward but had never broken through to see what lay beyond the Blue Ridge: Lee's entire infantry army, marching north for Pennsylvania. The three-week delay before Gettysburg can be measured in part by the time Stuart bought on these farms and ridges in Loudoun County.