Upperville
John Buford's Federal column had detoured to attack the new Confederate left flank near Upperville, while J. Irvin Gregg's and Judson Kilpatrick's brigades advanced from the east along the Ashby's Gap Turnpike. Buford soon encountered "Grumble" Jones and Chambliss's Confederate brigades, escorting Stuart's supply train just north of Upperville, and attacked. Meanwhile, Kilpatrick's troopers attacked Hampton and Robertson on a ridgeline east of Upperville known as Vineyard Hill. Some of the Union cavalrymen made it as far as the village before being repulsed.
After furious mounted fighting, Stuart finally withdrew to take a strong defensive position in Ashby's Gap, even as Confederate infantry began crossing the Potomac River into Maryland. As cavalry skirmishing diminished in the next few days, Stuart made the fateful decision to strike east and make a circuit of the Union army as it marched toward Gettysburg.
Upperville was significant in that Stuart's successful delaying tactics prevented Pleasonton from making an accurate assessment of the location of Lee's infantry divisions, thereby depriving the Federals of much valued intelligence of their enemy's whereabouts and objectives.
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