After initially holding off Kilpatrick's cavalry, Stuart, effectively using stone walls and steep ravines and creeks, began to fall back under pressure from the Union infantry.

He made a stand west of the hamlet of Rector's Crossroads along the stone bridge over Goose Creek, where for two more hours he was able to withstand repeated Federal attacks from mounted cavalry, as well as the 16th Michigan Infantry, which sent skirmishers and sharpshooters forward to pick off the Confederate gunners.

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.

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.