Battle of Middleburg The Battle of Middleburg took place from June 17 to June 19 , 1863 , in Loudoun County , Virginia , as part of the Gettysburg Campaign of the American Civil War . Confederate Maj . Gen . J . E . B . Stuart , screening Robert E . Lee ' s invasion route , sparred with Maj . Gen . Alfred Pleasonton ' s Union cavalry . On June 17 , Col . Alfred N . Duffié ' s isolated 1st Rhode Island Cavalry Regiment was attacked by the brigade s of Thomas T . Munford and Beverly Robertson . The 1st Rhode Island 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 . Skirmish of June 17 . Stuart established his headquarters at Middleburg and scattered his brigades throughout the Loudoun Valley to watch for enemy activity . Early in the morning , Col . Duffié , a French - born officer , had taken the 280 men of the 1st Rhode Island Cavalry westward from the Army of the Potomac ' s camp near Centreville . Pleasonton had ordered him to camp at Middleburg that evening and then to proceed the next day toward Noland ' s Ferry , extending his march to the west as far as Snickersville . Duffié crossed the Bull Run Mountains at Thoroughfare Gap at 9 : 30 a . m . , easily pushing aside pickets from John R . Chambliss ' s brigade . Confederate commanders could not believe that a small Union regiment would dare to travel so deep into enemy territory without an escort , so Chambliss did not aggressively attack , fearing that the column was the advance element of a much larger enemy force . Duffié continued on his isolated march , turning to the north by 11 : 00 a . m . and heading for Middleburg as ordered . Arriving there about 4 : 00 p . m . , Duffié drove in the few Confederate pickets deployed there and disrupted Stuart ' s evening of socializing with local ladies . Stuart and his staff quickly retreated to Rector ' s Crossroads , the location of his closest brigade . He ordered Beverly Robertson to move immediately to Middleburg to crush the Union cavalry . Duffié barricaded the streets of Middleburg , dismounted half of his regiment behind stonewalls , and sent for help from Judson Kilpatrick ' s brigade near Aldie . At 7 : 00 p . m . , Stuart ' s attack routed the vastly outnumbered Rhode Islanders . Many of Duffié ' s men were captured the next morning as Chambliss cut off their escape route . The Parisian colonel finally returned to Centreville with only 4 officers and 27 men . A few stragglers eventually rejoined the shattered remnants of the regiment . Duffié would never again serve with the Army of the Potomac , although he did command cavalry in other Union armies . The Union casualties on July 17 were reported as 250 . Fight on June 19 . After the Battle of Aldie , Stuart remained on the defensive , wanting to spoil any Federal attempts to force the passes in the Blue Ridge Mountains . Pleasonton tentatively sent probes towards Ashby ' s and Snicker ' s Gaps . On June 18 , David McM . Gregg ran into Confederate pickets around Middleburg , and Stuart quickly fell back to a commanding ridge west of town . Fearing a trap , a cautious Pleasonton ordered Gregg to withdraw to Aldie . The next day , Gregg again moved against Middleburg , sending the brigade of his first cousin , Col . J . Irvin Gregg , at the Rebels while John Buford ' s division swung north towards Pot House ( New Lisbon ) . After a flanking march , Buford eventually occupied the ground around Pot House , pushing back two regiments of William " Grumble " Jones ' s brigade in a mild skirmish . After a hard fight to clear reinforced pickets from Middleburg , Colonel Gregg was so impressed by the Confederate position on the high ground beyond the town that he asked for support before attacking . Kilpatrick sent two regiments to help extend the Federal line , and Gregg slowly advanced . The temperature hovered around 98 °F throughout the afternoon , sapping men and horses of energy . A series of Union charges finally forced Stuart ' s horse artillery to withdraw , and then his cavalry . Several Confederate counterattacks failed to regain control of the ridge . Late in the day , Buford sent the U . S . Reserve Brigade back from Pot House , and the 2nd and 6th U . S . Cavalry regiments seized a hotly contested hill south of the tiny village of Millville as darkness fell . Stuart was forced to abandon his position , falling back along the turnpike to stonewalls beyond a ravine along a stream known as Kirk ' s Branch . A still cautious Pleasonton refused to follow up his success and ordered his men to rest and send out pickets . Union losses in the June 19 fight were reported as 16 killed , 46 wounded , and 37 missing . Stuart lost perhaps 40 men , including his chief of staff and friend , Heros von Borcke from Prussia , who was badly wounded by a bullet in his neck .