Battle of Aldie The Battle of Aldie took place on June 17 , 1863 , in Loudoun County , Virginia , as part of the Gettysburg Campaign of the American Civil War . Maj . Gen . J . E . B . Stuart ' s cavalry screened Gen . Robert E . Lee ' s Confederate infantry as it marched north in the Shenandoah Valley behind the sheltering Blue Ridge Mountains . The pursuing Union cavalry of Brig . Gen . Judson Kilpatrick ' s brigade , in the advance of Brig . Gen . David McM . Gregg ' s division , encountered Col . Thomas T . Munford ' s troopers near the village of Aldie , resulting in four hours of stubborn fighting . Both sides made mounted assaults by regiment s and squadrons . Kilpatrick was reinforced in the afternoon , and Munford finally withdrew toward Middleburg . Background . Late in the spring of 1863 tensions grew between Union commander Joseph Hooker and his cavalry commander Brig . Gen . Alfred Pleasonton because of the latter ' s inability to penetrate Maj . Gen . J . E . B . Stuart ' s cavalry screen and gain access to the Shenandoah Valley to locate the Army of Northern Virginia , which had been on the move since the Battle of Chancellorsville in early May . On June 17 , Pleasonton decided to push through Stuart ' s screen . To accomplish his goal he ordered Brig . Gen . David McM . Gregg ' s division from Manassas Junction westward down the Little River Turnpike to Aldie . Aldie was tactically important in that near the village the Little River Turnpike intersected both the Ashby ' s Gap Turnpike and Snicker ' s Gap Turnpike , which respectively lead through Ashby ' s Gap and Snickers Gap of the Blue Ridge Mountain into the Valley . Battle . Early that very same morning , Colonel Munford led the 2nd and 3rd Virginia Cavalry eastward across the Loudoun Valley from Upperville through Middleburg to Aldie on the Bull Run Mountains on a reconnaissance and forage mission . He established a line of pickets in Aldie to watch for enemy activity and withdrew his two regiments northwest of town on the Snicker ' s Gap Turnpike to camp on the farm of Franklin Carter . About 4 p . m . , Gregg ' s advance column of the 2nd and 4th New York , 6th Ohio , 1st Maine , 1st Rhode Island , and 1st Massachusetts , under the command of Brig . Gen . Judson Kilpatrick arrived in Aldie . Just west of the village the 1st Massachusetts encountered Munford ' s pickets and drove them back . Around the same time , the rest of Munford ' s brigade ( the 1st , 4th , and 5th Virginia Cavalry , under the command of Col . Williams Carter Wickham ) arrived at Dover Mills , a small hamlet on the Little River west of Aldie . Wickham ordered Col . Thomas L . Rosser to take the 5th Virginia to locate a campsite closer to Aldie . As they moved east they ran into the Massachusetts men and easily drove them back through Aldie to the main Union body . After positioning his sharpshooters ( 50 men of Company I under Capt . Reuben F . Boston ) east of the William Adam farmhouse , Rosser deployed west along a ridge that covered the two roads leading out of Aldie and awaited the arrival of the Federals , as well as Munford and Wickham . As Rosser withdrew west , the 1st Massachusetts , with aid from the 4th New York , charged against what they believed to be a retreat . Rosser ' s line held and he mounted a countercharge in concert with a sharp volley from the sharpshooters he had placed on his left and easily drove the Federals back , securing his hold on the Ashby ' s Gap Turnpike . Kilpatrick then turned his attention towards the Snicker ' s Gap Turnpike . An artillery duel ensued and more cavalry on both sides soon arrived . A furious fight erupted , which at first went in favor of Munford as Federal charges were met , stopped , and then forced back by the withering volley of sharpshooters entrenched along a stone wall . The 1st Massachusetts Cavalry was trapped in a blind curve on the Snicker ' s Gap Turnpike and was destroyed , losing 198 of 294 men in the eight companies that were engaged . One detachment under Henry Lee Higginson was virtually wiped out in hand - to - hand fighting . The tide finally turned as Union reinforcements charged into the fray in the fading light and the 6th Ohio overran Boston ' s detachment on the Ashby ' s Gap Turnpike , capturing or killing most of his men . The fighting died down around 8 p . m . as Munford withdrew his command west towards Middleburg . Aftermath . Munford did not consider Aldie as a defeat as his withdrawal coincided with an order from Stuart to retire , as more Federal cavalry had been sighted at Middleburg . Union casualties were 305 dead and wounded , with the Confederates losing between 110 and 119 . Aldie was the first in a series of small battles along the Ashby ' s Gap Turnpike in which Stuart ' s forces successfully delayed Pleasonton ' s thrust across the Loudoun Valley , depriving him of the opportunity to locate Lee ' s army . Battlefield . Although not protected , the battlefield remains largely intact . Aldie and its mill look much as they did at the time of the battle . Widening of U . S . Route 50 has compromised the portion of the battlefield along the Ashby ' s Gap Turnpike . The stone wall and farmsteads remain intact along the Snicker ' s Gap Turnpike ( present day Route 734 ) . At the site of the stone wall along the blind curve where the 1st Massachusetts was decimated , a monument erected by the survivors stands to honor the service during the battle . On May 8 , 2012 , Gov . Bob McDonnell announced the preservation of a five - acre site to be purchased by the Civil War Trust and later to be operated as a passive historic interpretative site by the park authority . The land is along the Loudoun / Fauquier county border and was key to the June 17 – 21 , 1863 , Battles of Aldie , Middleburg , and Upperville .