Battle of Cross Keys The Battle of Cross Keys was fought on June 8 , 1862 , in Rockingham County , Virginia , as part of Confederate Army Maj . Gen . Thomas J . " Stonewall " Jackson ' s campaign through the Shenandoah Valley during the American Civil War . Together , the battles of Cross Keys and Port Republic the following day were the decisive victories in Jackson ' s Valley Campaign , forcing the Union armies to retreat and leaving Jackson free to reinforce Gen . Robert E . Lee for the Seven Days Battles outside Richmond , Virginia . Background . The hamlet of Port Republic , Virginia , lies on a neck of land between the North and South Rivers , which conjoin to form the South Fork Shenandoah River . On June 6 – 7 , 1862 , Jackson ' s army , numbering about 16 , 000 , bivouacked north of Port Republic , Maj . Gen . Richard S . Ewell ' s division along the banks of Mill Creek near Goods Mill , and Brig . Gen . Charles S . Winder ' s division on the north bank of North River near the bridge . The 15th Alabama Infantry regiment was left to block the roads at Union Church . Jackson ' s headquarters were in Madison Hall at Port Republic . The army trains were parked nearby . Two Union columns converged on Jackson ' s position . The army of Maj . Gen . John C . Frémont , about 15 , 000 strong , moved south on the Valley Pike and reached the vicinity of Harrisonburg on June 6 . The division of Brig . Gen . James Shields , about 10 , 000 , advanced south from Front Royal in the Luray ( Page ) Valley , but was badly strung out because of the muddy Luray Road . At Port Republic , Jackson possessed the last intact bridge on the North River and the fords on the South River by which Frémont and Shields could unite . Jackson determined to check Frémont ' s advance at Mill Creek , while meeting Shields on the east bank of the South Fork of the Shenandoah River . A Confederate signal station on Massanutten monitored Union progress . Early in the morning on June 8 , Frémont ' s men encountered the Confederate advanced guard near Cross Keys Tavern . A few shots were fired and the Union cavalry fell back onto their main body , which was approaching . Darkness prevented further developments . Battle . Colonel Samuel S . Carroll , at the head of a regiment of Union cavalry , supported by an artillery battery and a brigade of infantry , was sent ahead by Shields to secure the North River Bridge at Port Republic . Shortly after dawn ( June 8 ) , Carroll scattered the Confederate pickets , forded the South River , and dashed into Port Republic . Jackson and his staff raced down the main street from headquarters and across the bridge , narrowly eluding capture ( three members of his staff were captured : Col . Stapleton Crutchfield , Lt . Edward Willis , and Dr . Hunter McGuire ) . Carroll deployed one gun aimed at the bridge and brought up another . Jackson directed the defense , ordering Captain William T . Poague ' s battery to unlimber on the north bank . Captain James McD . Carrington brought up a gun from the vicinity of Madison Hall to rake the Main Street . Col . Samuel V . Fulkerson led his 37th Virginia Infantry in a charge across the bridge , where the gun at the opposite end was firing on them with grape shot , to drive the Union cavalry out of the town . Carroll retreated in confusion , losing his two guns , before his infantry could come within range . Three Confederate batteries unlimbered on the bluffs east of Port Republic on the north bank of the South Fork and fired on the retreating Federals . Carroll retired several miles north on the Luray Road . Jackson stationed Brig . Gen . William B . Taliaferro ' s brigade in Port Republic and positioned the Stonewall Brigade near Bogota with the artillery to prevent any further surprises . Meanwhile , Frémont , with Col . Gustave P . Cluseret ' s brigade in the lead , renewed his advance from the vicinity of Harrisonburg . After driving away the Confederate skirmishers , Cluseret reached and deployed his right flank along the Keezletown Road near Union Church . One by one , the Union brigades came into line : Brig . Gen . Robert C . Schenck on Cluseret ' s right , Brig . Gen . Robert H . Milroy on his left , and Brig . Gen . Julius H . Stahel on the far left , his left flank near Congers Creek . Brig . Gen . William H . C . Bohlen ' s and Col . John A . Koltes ' s brigades were held in reserve near the center of the line . A regiment of Union cavalry moved south on the road to secure the right flank . Batteries were brought to the front . Ewell deployed his infantry division behind Mill Creek , Brig . Gen . Isaac R . Trimble ' s brigade on the right across the Port Republic Road , Brig . Gen . Arnold Elzey ' s in the center along the high bluffs . Ewell concentrated his artillery ( 4 batteries ) at the center of the line . As Union troops deployed along Keezletown Road , Trimble advanced his brigade a quarter of a mile to Victory Hill and deployed Courtenay ' s ( Latimer ' s ) battery on a hill to his left supported by the 21st North Carolina Infantry . The 15th Alabama , which had been skirmishing near Union Church , rejoined the brigade . Trimble held his regiments out of sight behind the crest of the hill . Frémont determined to advance his battle line with the evident intention of enveloping the Confederate position , assumed to be behind Mill Creek . This maneuver required an elaborate right wheel . Stahel ' s brigade on the far left had the farthest distance to cover and advanced first . Milroy moved forward on Stahel ' s right and rear . Union batteries were advanced with infantry lines south of Keezletown Road and engaged Confederate batteries . Stahel appeared oblivious to Trimble ' s advanced position . His battle line passed down into the valley , crossed the run , and began climbing Victory Hill . At a distance of " sixty paces " , Trimble ' s infantry stood up and delivered a devastating volley . Stahel ' s brigade recoiled in confusion with heavy casualties . The Union brigade regrouped on the height opposite Victory Hill but made no effort to renew their assault . Stahel did not renew his attack but brought up a battery ( Buell ' s ) to support his position . Trimble moved the 15th Alabama by the right flank and up a ravine to get on the battery ' s left . In the meantime , Ewell sent two regiments ( 13th and 25th Virginia ) along the ridge to Trimble ' s right , attracting a severe fire from the Union battery . With a shout , the 15th Alabama emerged from their ravine and began to climb the hill toward the battery , precipitating a melee . Trimble advanced his other two regiments ( 16th Mississippi Infantry on the left and 21st Georgia Infantry on the right ) from their position on Victory Hill , forcing back the Union line . The Union battery limbered hastily and withdrew , saving its guns . A Union regiment counterattacked briefly , striking the left flank of the 16th Mississippi , but was forced back in desperate fighting . Trimble continued advancing up the ravine on the Confederate right , outflanking successive Union positions . In the meantime , Milroy advanced on Stahel ' s right , supported by artillery . Milroy ' s line came within rifle - musket range of the Confederate center behind Mill Creek and opened fire . Union batteries continued to engage Confederate batteries in an artillery duel . Bohlen advanced on the far Union left to stiffen Stahel ' s crumbling defense . Milroy ' s left flank was endangered by Stahel ' s retreat , and Frémont ordered him to withdraw . Jackson brought Taylor ' s brigade forward to support Ewell if needed , but Taylor remained in reserve on the Port Republic Road near the Dunker Church . Seemingly paralyzed by the decimation of Stahel ' s brigade on his left , Frémont was unable to mount a coordinated attack . He ordered Schenck ' s brigade forward to find the Confederate left flank south of Union Church . Ewell reinforced his left with elements of Elzey ' s brigade . Severe firing erupted along the line but quickly died down . Confederate Brig . Gen . Elzey and Brig . Gen . George H . Steuart were wounded in this exchange . Frémont withdrew his force to Keezletown Road , placing his artillery on the heights to his rear ( Oak Ridge ) . Artillery firing continued . Aftermath . Union casualties totaled 557 killed and wounded and 100 captured , while the Confederates lost fewer than 300 men . At dusk , Trimble pushed his battle line forward to within a quarter mile of the Union position , anticipating a night assault . Confederate accounts describe the Union soldiers going into camp , lighting fires , and making coffee . Schenck sent out a company to probe the Confederate positions after dark , but after a brief skirmish the company withdrew and no other engagements took place . During the night , Ewell ordered Trimble to withdraw without making the attack .