Prelude: On 21 May 1862, the US army under Maj. Gen. Nathaniel P. Banks, numbering about 9,000 men, was concentrated in the vicinity of Strasburg with two companies of infantry at Buckton Depot. Col. J. R. Kenly commanded 1,063 men and two guns at Front Royal. CS 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 22 May, Maj. Gen. Thomas J. 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 Munford's cavalry regiment was sent east to close off Manassas Gap and cut communication between Front Royal and Washington.

Phase One. CS Advance: On the morning of 23 May, the vanguard of Jackson's army reached Spangler's crossroads (present day Limeton). Here the CS cavalry under colonels Ashby and Flournoy diverged west to cross the South Fork Shenandoah 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.

Phase Two. Deployment of Forces: Jackson's leading brigade, Taylor's, deployed on Prospect Hill and along the ridge to the east. The 1st Maryland and Wheat's Louisiana battalion were thrown out in advance, entering the town and clearing it of US skirmishers. Col. J. R. Kenly, in command of US forces, withdrew his force to Camp (Richards') Hill, supported by a section of artillery. The US 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 CS advance. Kenly's headquarters were in the Vanoort House.

Phase Three. US Defense of Camp Hill: The Confederate infantry advanced through town, deploying into line of battle under an accurate artillery fire. A CS flanking column moved to the east, crossing Happy Creek in an attempt to force US 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.

Phase Four. Skirmish at Buckton Depot: In the meantime, after crossing the South Fork at McCoy's Ford, Ashby's and Lt. Col. Flournoy's (6VA) cavalry rode via Bell's Mill and Waterlick Station to reach the US outpost at Buckton Depot. Ashby made a mounted assault, which cost him several of his best officers before the US defenders surrendered. Ashby cut the telegraph lines, severing communication between the main US 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.

Phase Five. US Retreat: 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. He positioned part of his command at Guard Hill, while the Confederates ran forward to douse the flames, saving the bridges. While CS 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 CS infantry crossed, the US 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.

Phase Six. US Surrender: Kenly withdrew along the Winchester turnpike beyond Cedarville with Flournoy's cavalry in close pursuit. General Jackson rode ahead with the cavalry, as CS 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 US flanks, causing panic. Kenly fell wounded, and the US defense collapsed. More than 700 US soldiers threw down their weapons and surrendered.