Maj. Gen. J.E.B. Stuart, screening Lee’s invasion route, sparred with Pleasonton’s cavalry. On the June 17, Col. Alfred Duffié’s isolated 1st Rhode Island Cavalry Regiment was attacked by the brigades of Munford and Robertson. The 1st Rhode Island Cavalry was routed, taking about 250 casualties. On June 19, J. Irvin Gregg’s brigade advanced, driving Stuart’s cavalry one mile beyond the town. Both sides were reinforced and mounted and dismounted skirmishing continued. Stuart was gradually levered out of his position but fell back to a second ridge, still covering the approaches to the Blue Ridge gap.
Source
CWSAC Battle Summaries, National Park Service (http://www2.cr.nps.gov/abpp/battles/bycampgn.htm)
The Battle of Upperville took place on June 21, 1863, in Loudoun County, Virginia, as part of the Gettysburg Campaign of the American Civil War.
Stuart had slowed the Federals in fighting at Aldie and Battle of Middleburg, using ravines, creeks, and stonewalls to his advantage as he slowly withdrew westward.
Following the fighting at Middleburg on June 19, a heavy rainstorm during the night had soaked the Loudoun Valley, ending a six-week drought.