Fight at Aldie The Fight at Aldie was a small cavalry skirmish between Confederate forces under Major John S . Mosby and Union forces under Major Joseph Gilmore and Captain Franklin T . Huntoon in Aldie , Virginia , on March 2 , 1863 , as part of Mosby ' s Operations in Northern Virginia during the American Civil War . The fight which resulted in a Confederate victory was significant in that it was the first action of Mosby ' s Rangers within their operating territory in the central Loudoun Valley . In the fight Mosby and his men displayed many characteristics that would become their hallmark including the attack on numerically superior force while inflicting disproportionate casualties to those received . Background . On January 24 , 1863 , Maj . Gen . J . E . B . Stuart dispatched his scout John S . Mosby and 15 of his cavaliers to the lower Loudoun Valley in Fauquier County to conduct operations against Union forces occupying Northern Virginia . On January 28 , the small band met at Mount Zion church , east of Aldie and set on their first raid against Federals in Chantilly . During the next month , Mosby and his men raided into Fairfax County twice more , besting larger Federal forces each time . On March 2 , in response to the raids , Colonel Sir Percy Wyndham dispatched 200 troopers of the 18th Pennsylvania under Major Joseph Gilmore from Fairfax towards Middleburg to find and capture Mosby and his men . In the town , the Union force , many of whom were reportedly drunk , began searching local residences and arresting citizens in an attempt to smoke out Mosby ' s men . When this proved to be unsuccessful , Gilmore threatened to burn the town . Residents of the village , pleaded with Gilmore to spare them , claiming to have no knowledge of the whereabouts of Mosby ' s men . Gilmore apparently believed them and withdrew with his command east , toward Aldie . At Aldie , the 18th Pennsylvania encountered a 50 - man detachment of the 1st Vermont on similar patrol in Loudoun . The drunken Major Gilmore mistook the 1st Vermont for Confederates and ordered a retreat . The 1st Vermont , overtook the 18th Pennsylvania and the mistake was recognized . The 18th Pennsylvania informed the 1st Vermont of their failure to locate Mosby and then withdrew for Fairfax , while the 1st Vermont returned to Aldie to water their mounts . The fight . The Federal raid on Middleburg did not go unnoticed by Mosby . As soon as the Federals left the town , he quickly assembled as many men as possible , totaling between 17 and 28 , and then set out towards Aldie in pursuit . As Mosby ' s men entered the village from the west , they spied the dismounted 1st Vermont . Mosby immediately ordered a charge and with a yell the Confederates bore down on the Federals , taking them by surprise and sending most of them into a wild retreat . In the midst of the charge , Mosby lost control of his horse and was forced to jump off , losing it to the Federals . During the fight Captain John W . Woodward of the 1st Vermont had his horse shot out from underneath him , pinning him to the ground . One of Mosby ' s men ran towards him to shoot him , but Woodward was able to draw a concealed pistol and shoot his assailant . Believing that Woodward had already surrendered when he fired the shot a few of Mosby ' s men rushed in to execute him , but Mosby , who witnessed the affair , quickly interceded , taking the captain prisoner . Aftermath . Despite losing his horse , Mosby and his men handled themselves well , capturing 19 Federals , including two captains and 23 horses , while suffering only one wounded . In response to the raid into his territory , Mosby planned another raid on Federals in Fairfax to capture the cavalry commander Sir Percy Wyndham on March 9 . The result of this action would be Mosby ' s most famous exploit of the war , the Stoughton Raid . In addition , for defending the town of Middleburg and severely embarrassing the Federals sent to raid it , Mosby and his men won the admiration of the town ' s citizens , who had to this point been weary of the partisans . The support of the people of the Loudoun Valley would become one of Mosby ' s greatest assets for the duration of the war .