First Battle of Winchester The First Battle of Winchester , fought on May 25 , 1862 , in and around Frederick County , Virginia , and Winchester , Virginia , was a major victory in Confederate Army Maj . Gen . Thomas J . " Stonewall " Jackson ' s Campaign through the Shenandoah Valley during the American Civil War . Jackson enveloped the right flank of the Union Army under Maj . Gen . Nathaniel P . Banks and pursued it as it fled across the Potomac River into Maryland . Background . Maj . Gen . Nathaniel P . Banks learned on May 24 , 1862 , that the Confederates had captured his garrison at Front Royal , Virginia , and were closing on Winchester , turning his position . He ordered a hasty retreat down the Valley Pike from Strasburg . His columns were attacked at Middletown and again at Newtown ( Stephens City ) by Jackson ' s converging forces . The Confederates took many Union prisoners and captured so many wagons and stores that they later nicknamed the Union general " Commissary Banks " . Jackson pressed the pursuit for most of the night and allowed his exhausted soldiers only a few hours sleep before dawn . Banks now deployed at Winchester to slow the Confederate pursuit . He had two brigades of infantry under Colonels Dudley Donnelly and George Henry Gordon , a mixed brigade of cavalry under Brig . Gen . John P . Hatch , and 16 guns . Gordon ' s brigade was placed on the Union right on Bower ' s Hill with its left flank at the Valley Pike , supported by a battery of artillery . The center of the line ( Camp Hill ) was held by the cavalry supported by two guns . Donnelly ' s brigade was placed in a crescent on the left to cover the Front Royal and Millwood roads with the rest of the artillery . At earliest light the Confederate skirmish line advanced in force driving the Union pickets back to their main line of battle . Battle . During the night , the advance of Maj . Gen . Richard S . Ewell ' s division ( four brigades ) reached Buffalo Lick . Jackson moved three of Ewell ' s brigades to the left to participate in the advance on the Valley pike , leaving Ewell with just Trimble ' s brigade and Bradley Johnson ' s Maryland regiment . At dawn , he deployed Trimble ' s brigade astride the Front Royal Pike and advanced against the Union left flank . His leading regiments ( in particular the 21st North Carolina ) came under heavy fire from Union forces deployed behind stone fences and were repulsed . Confederate forces regrouped and brought up artillery . Ewell advanced the regiments of Trimble ' s brigade , sending regiments to either side of the high ground to enfilade the Union position . Donnelly withdrew his brigade to a position closer to town with his right flank anchored on Camp Hill . Ewell then attempted a flanking movement to the right beyond the Millwood Road , but in response to orders from Banks , Donnelly withdrew through the town . In conjunction with Ewell ' s advance on the Front Royal Pike , Jackson advanced on the Valley Pike at early dawn in a heavy fog . At Jackson ' s command , Winder ' s brigade swept over a hill to the left of the pike , driving off the Union skirmishers who held it . Jackson quickly placed a section of artillery on the hill to engage Union artillery on Bower ' s Hill at a range of less than half a mile . Union sharpshooters along Abrams Creek began picking off the cannoneers . Jackson brought up the rest of his artillery and a duel ensued with the Union guns on Bower ' s Hill . Jackson then brought up the brigades of Fulkerson , Campbell and Elzey to support Winder . Then Jackson deployed Brig . Gen . Richard Taylor ' s Louisiana brigade ( led by the Louisiana Tigers ) reinforced by two regiments of Fulkerson ' s brigade and backed up by Scott ' s brigade , to the left along Abrams Creek . Taylor marched under fire to a position overlapping the Union right and then attacked Bower ' s Hill . The Confederate assault swept irresistibly forward over the crest in the face of determined resistance . With three enemy brigades in its front and three coming at its right flank , Gordon ' s Union brigade gave way and Union soldiers began streaming back into town . Union forces retreated through the streets of Winchester and north on the Valley Pike to Martinsburg . After resting in Martinsburg , Banks command continued north to the Potomac river , crossing it at Williamsport . Confederate pursuit was lethargic , as the troops were exhausted from the non - stop marching of the previous week under Jackson ' s command . Nevertheless , many Union prisoners fell into Confederate hands . Brig . Gen . Turner Ashby ' s cavalry was disorganized from the actions of May 24 and did not pursue until Banks had already reached the Potomac River . Aftermath . First Winchester was a major victory in Jackson ' s Valley Campaign . The ultimate significance of Jackson ' s victory at Winchester was its strategic impact . Union plans for a convergence on Richmond were disrupted by Jackson ' s audacity , and thousands of Union reinforcements were diverted to the Valley and the defense of Washington , D . C .