Battle of Upperville The Battle of Upperville took place in Loudoun County , Virginia on June 21 , 1863 during the Gettysburg Campaign of the American Civil War . Background . The Union cavalry made a determined effort to pierce Confederate Maj . Gen . J . E . B . Stuart ' s cavalry screen . Stuart had been fighting a series of delaying actions in the Loudoun Valley , hoping to keep Union General Alfred Pleasonton ' s cavalry from discovering the location of the main body of Robert E . Lee ' s Army of Northern Virginia , much of which was in the Shenandoah Valley just west of the small village of Upperville . 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 . He made another determined stand near Upperville and succeeded in preventing the Federal cavalry from entering the Shenandoah Valley . Goose Creek . Following the fighting at Middleburg on June 19 , a heavy rainstorm during the night had soaked the Loudoun Valley , ending a six - week drought . In the downpour , Wade Hampton ' s brigade of Confederate cavalry had reinforced J . E . B . Stuart , and was deployed near Beverly Robertson ' s brigade along the Ashby ' s Gap Turnpike . John R . Chambliss ' s brigade moved northward and joined " Grumble " Jones near Unison , Virginia . Thomas T . Munford ' s brigade was still farther north , guarding access to the Snickersville Gap . John Mosby ' s partisan rangers scouted the Union positions and provided much needed intelligence on their movements . Union cavalry commander Alfred Pleasonton , frustrated by Stuart ' s excellent usage of dismounted cavalry hiding behind stone walls , on June 20 asked for and received infantry support from Maj . Gen . George G . Meade ' s V Corps . Pleasonton had still not located Lee ' s main body , a task that the War Department continued to prod him to accomplish . Trying to maneuver Stuart out of position , Pleasonton sent Judson Kilpatrick ' s brigade along the Ashby ' s Gap Turnpike , supported by Col . Strong Vincent ' s brigade of infantry , with David McM . Gregg ' s cavalry division in reserve . John Buford ' s division would try to turn the flank . Stuart , determined to rest his weary men on the Sabbath , did not get his wish , as Federal artillery opened up on his position around 8 : 00 a . m . on June 21 . 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 sharpshooter s forward to pick off the Confederate gunners . Ahead of the advancing Union soldiers , the Confederate artillerymen hooked up their guns to their teams and raced off , but a Blakely Rifle flipped over as its crew hurried to get away . The gun was captured , the first artillery piece ever lost by Stuart ' s cavalry . However , with two of his three remaining guns soon also disabled , Stuart withdrew and headed westward toward Upperville , still fighting delaying actions where favorable . 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 .