Battle of Front Royal The Battle of Front Royal , also known as Guard Hill or Cedarville , was fought May 23 , 1862 , in Warren County , Virginia , as part of Confederate Army Maj . Gen . Thomas J . " Stonewall " Jackson ' s Campaign through the Shenandoah Valley during the American Civil War . Front Royal demonstrated Jackson ' s use of Valley topography and mobility to unite his own forces while dividing those of his enemies . At a minimal cost , he forced the withdrawal of a large Union army by striking at its flank and threatening its rear . Background . On May 21 , 1862 , the Union army under Maj . Gen . Nathaniel P . Banks , numbering about 9 , 000 men , was concentrated in the vicinity of Strasburg , Virginia , with two companies of infantry at Buckton Depot . Col . John R . Kenly commanded 1 , 063 men and two guns at Front Royal . Confederate cavalry under Col . Turner Ashby confronted Banks near Strasburg , but then withdrew to join the main army , which crossed Massanutten Mountain via New Market Gap to reach Luray , Virginia . On May 22 , Jackson ' s Army of the Valley ( about 16 , 500 men ) advanced along the muddy Luray Road to within ten miles of Front Royal . Jackson ' s headquarters were at Cedar Point . Colonel Thomas T . Munford ' s cavalry regiment was sent east to close off Manassas Gap and cut communication between Front Royal and Washington , D . C . Battle . On the morning of May 23 , the vanguard of Jackson ' s army reached Spangler ' s Crossroads ( present day Limeton , Virginia ) . Here the Confederate cavalry under colonels Ashby and Thomas Flournoy diverged west to cross the South Fork of the Shenandoah River at McCoy ' s Ford . The infantry continued to Asbury Chapel and right onto a cross road to reach Gooney Manor Road . Following this road , they approached Front Royal from the south , bypassing Federal pickets stationed near the river on the Luray Road one mile south of the courthouse . After minor skirmishing the Federals withdrew . Jackson ' s leading brigade , under the leadership of Brig . Gen . Richard Taylor , deployed on Prospect Hill and along the ridge to the east . The 1st Maryland Infantry , CSA and Major Roberdeau Wheat ' s Louisiana " Tigers " battalion were thrown out in advance , entering the town and clearing it of Union skirmishers . The battle is notable in that the 1st Maryland CSA was thrown into battle with their fellow Marylanders , the Union 1st Regiment Maryland Volunteer Infantry . , the only time in United States military history that two regiments of the same numerical designation and from the same state have engaged each other in battle . On the day of the battle Captain William Goldsborough of the 1st Maryland Infantry , CSA captured his brother Charles Goldsborough of the 1st Maryland Infantry , USA , and took him prisoner . Col . Kenly , in command of Union forces , withdrew his force to Camp ( Richards ' ) Hill , supported by a section of artillery . The Union line extended in an arc from the South Fork to Happy Creek , defending the South Fork bridge . Kenly ' s artillery opened fire and slowed the Confederate advance . Kenly ' s headquarters were in the Vanoort House . The Confederate infantry advanced through town , deploying into line of battle under an accurate artillery fire . A Confederate flanking column moved to the east , crossing Happy Creek in an attempt to force Union withdrawal without a frontal assault . After a long delay because of the muddy roads , a battery of rifled artillery was deployed on or near Prospect Hill to counter the Union guns on Camp Hill . In the meantime , after crossing the South Fork at McCoy ' s Ford , Ashby ' s and Lt . Col . Flournoy ' s 6th Virginia Cavalry rode via Bell ' s Mill and Waterlick Station to reach the Union outpost at Buckton Depot . Ashby made a mounted assault , which cost him several of his best officers before the Union defenders surrendered . Ashby cut the telegraph lines , severing communication between the main Union army at Strasburg and the detached force at Front Royal . He then divided the cavalry , sending Flournoy ' s regiment east toward Riverton to threaten Kenly ' s rear . Ashby remained at Buckton Depot astride the railroad to prevent reinforcements from being sent to Front Royal . On discovering that Confederate cavalry was approaching from the west , Col . Kenly abandoned his position on Camp Hill , retreated across the South and North Fork bridges , and attempted to burn them . Sgt . William Taylor received the Medal of Honor for his gallantry in this action . Kenly positioned part of his command at Guard Hill , while the Confederates ran forward to douse the flames , saving the bridges . While Confederate infantry repaired the bridges for a crossing , Flournoy ' s cavalry arrived at Riverton and forded the river , pressing Kenly ' s forces closely . As soon as the Confederate infantry crossed , the Union position could be flanked by a column moving along the river . Kenly chose to continue his withdrawal , his outmatched cavalry fighting a rear guard action against Flournoy ' s 6th Virginia Cavalry . Kenly withdrew along the Winchester turnpike beyond Cedarville , Virginia , with Flournoy ' s cavalry in close pursuit . Jackson rode ahead with the cavalry , as Confederate infantry began to cross the rivers . At the Thomas McKay House , one mile north of Cedarville , Kenly turned to make a stand , deploying on the heights on both sides of the pike . Flournoy ' s cavalry swept around the Union flanks , causing panic . Kenly fell wounded , and the Union defense collapsed . More than 700 Union soldiers threw down their weapons and surrendered . Aftermath . The results of the battle were lopsided . Union casualties were 773 , of which 691 were captured . Confederate losses were 36 killed and wounded . Jackson ' s victory over the small Union force at Front Royal forced the main Union Army at Strasburg under Banks into abrupt retreat . Jackson deceived Banks into believing that the Confederate army was in the main Valley near Harrisonburg ; instead he had marched swiftly north to New Market and crossed Massanutten via New Market Gap to Luray . The advance to Front Royal placed Jackson in position to move directly on Winchester , Virginia , in the rear of the Union army . On May 24 , Banks retreated down the Valley Pike to Winchester , harassed by Confederate cavalry and artillery at Middletown and Newtown ( Stephens City ) , setting the stage for the First Battle of Winchester the following day . The confusion engendered by Jackson ' s appearance at Front Royal and the hasty Union retreat from Strasburg to Winchester contributed materially to the defeat of Banks ' s army at First Winchester on May 25 . Jackson used his cavalry to good advantage at Front Royal , to sever Union communications east and west , and to strike the final blow at Cedarville . After the battle , the victorious First Maryland CSA took charge of prisoners from the beaten Union First Maryland regiment . Many men recognized among them former friends and family . According to J . J . Goldsborough , who chronicled the history of the Maryland Line in the Confederate Army :