Battle of Charlestown The Battle of Charlestown was a small engagement between Confederate cavalry forces under Brig . Gen . John D . Imboden and the Union forces under Col . Benjamin L . Simpson on October 18 , 1863 , at Charlestown , West Virginia , as part of the Bristoe and Mine Run Campaign s , resulting in a Confederate victory . Background . As the Confederate Army of Northern Virginia and the Union Army of the Potomac dueled it out in central Virginia during the Bristoe campaign , General Robert E . Lee dispatched cavalry under Brig . Gen . John Imboden to raid in the Shenandoah Valley and attack the vulnerable Union garrison at Charlestown , West Virginia , in an effort to draw Union forces away from his front . By October 17 , Imboden ' s force had reached Berryville , where they skirmished with a company of the 1st New York Cavalry before driving them back to Charlestown . The presence of the confederates was reported to Benjamin Simpson , commander of the Charlestown garrison . The inexperienced Simpson , having been mustered into service only 17 days earlier , dismissed recommendations to fall back on the much more strongly defended Harpers Ferry , believing Charlestown was not the target of the Confederate raid . Battle . At dawn on the 18th , Union pickets south of Charlestown were driven back by Imboden ' s advance . Simpson ' s 9th Maryland Infantry , numbering some 375 men , took up position in the Jefferson County Courthouse ( in which John Brown was tried and hanged ) and ordered the cavalry , consisting of one company each of the Loudoun Rangers and 6th Michigan Cavalry , to " take care of themselves " . Upon entering town , Imboden sent a flag of truce to negotiate surrender , to which Simpson refused . The cavalry , seeing the hopelessness of the situation , decided to fight their way out and unite with the Harpers Ferry garrison . On the northeast outskirts of town , the Union cavalry encountered the 18th Virginia Cavalry and 62nd Virginia Mounted Infantry , who unleashed a volley at the column , sending several troopers and their horses to the ground . Those troopers who were still mounted broke left around their felled comrades and serendipitously rode into the Confederate right , which was proved to be its weak spot . The Union cavalry cut its way out , taking heavy losses : 17 captured , 2 killed and several wounded and nearly every horse shot , several killed . Meanwhile , back in Charlestown , Imboden brought up his artillery , and again demanded the garrison ' s surrender , which was rebuked for a second time , whereupon Imboden began to shell the town . Under the artillery fire , Simpson was forced to abandon the courthouse and marched his men to a field northwest of town , not far from the earlier cavalry engagement . Imboden massed his forces in a woods facing the field and unleashed a deadly volley . After several minutes and only a few shots fired in return , Simpson finally surrendered his force , now totaling some 365 men . The artillery fire had not gone unnoticed in nearby Harpers Ferry ; the 17th Indiana battery , Cole ' s Maryland Cavalry , and the remainder of the Loudoun Rangers and 6th Michigan , totaling 300 men in all , were dispatched to reinforce the besieged garrison . Within 15 minutes they had engaged Imboden ' s force and a fierce firefight ensued that lasted the entirety of the afternoon . The reinforcements , however , were not strong enough to drive off Imboden and liberate the prisoners . At around 5 p . m . the 34th Massachusetts Infantry , 400 strong , arrived , having been marched 18 miles from their camp at Berrysville to the sound of the artillery fire . As the sun set , the Bay Staters attacked Imboden , who with the cover of darkness elected to withdraw while still in possession of his prisoners and plunder from the town . Aftermath . Imboden successfully attacked and defeated the Union garrison at Charlestown , exposing the weakness of Union forces in the Shenandoah Valley , taking only light losses . While his raid was successful , it had little overall impact on the fall campaigns , which ended shortly thereafter as the two armies went into winter quarters . For the Union ' s part , at considerable loss , they saved Charlestown from being sacked and burned and turned back Imboden ' s raid , which if had been allowed to continue may have had a larger strategic impact on the campaign in central Virginia .