The Battle of Front Royal was also known as the Battle of Guard Hill or Cedarville. Front Royal demonstrated Maj. Gen. Thomas J. "Stonewall" Jackson's use of the 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.
After the Battle of McDowell, Maj. Gen. Thomas J. "Stonewall" Jackson moved back toward Harrisonburg where he had left Maj. Gen. Richard S. Ewell's division when he went west. Brig. Gen. James Shields had left the Shenandoah Valley, stationing Maj. Gen. Nathaniel Banks at Strasburg with about 8,000 men to block Jackson if he came north again. To protect the area abandoned by Shields, Banks sent 1,000 men and 2 guns to Front Royal, east of Strasburg on the Manassas Gap Railroad.
On May 21, the Union army under Maj. Gen. Nathaniel P. Banks, numbering about 9,000 men, was concentrated in the vicinity of Strasburg, with 2 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.
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. Col. Thomas Munford's cavalry regiment was sent east to close off Manassas Gap and cut communication between Front Royal and Washington, D.C.
On the morning of May 23, the vanguard of Jackson's army reached Spangler's crossroads. Here the Confederate cavalry under Ashby and Col. Thomas L. 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 Union 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, Maj. Gen. Richard Taylor's, deployed on Prospect Hill and along the ridge to the east. The 1st Maryland and Maj. Roberdeau Wheat's Louisiana "Tigers" battalion were thrown out in advance, entering the town and clearing it of Union skirmishers. Kenly, in command of Union forces, withdrew his force to Camp (Richards's) 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, Kenly abandoned his position on Camp Hill, retreated across the South and North Fork bridges, and attempted to burn them. He 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, 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.
Jackson's decisive 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, 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, setting the stage for the Battle of Winchester (First) 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.
Jackson was now located between Banks and Washington, D.C., while Winchester and Harpers Ferry were undefended. Both Jackson and Banks raced north, to meet again at Winchester on the 25th. On the peninsula, Maj. Gen. Irvin McDowell's army was called back from Maj. Gen. George McClellan's command near Richmond when Jackson became a new threat in the valley.