The Battles of Front Royal and First Winchester

by Jonathan A. Noyalas

Following the victory at McDowell, Stonewall Jackson returned his army to the Shenandoah Valley. Now Jackson set his sights on Gen. Nathaniel P. Banks’ Union force operating in the lower end of the Valley. Jackson’s men moved swiftly and by May 21 were near Luray where they linked with Gen. Richard S. Ewell’s division. Ewell had been in the Valley for several weeks keeping a keen eye on Banks’ movements while Jackson dealt with Frémont’s forces near McDowell. After Ewell joined forces with Jackson, Stonewall’s ranks swelled to approximately 17,000. This gave the Confederates a tremendous numerical advantage over Banks who had less than 10,000 troops spread throughout the region. The largest concentration was 4,500 men near Strasburg, while 2,500 infantrymen defended the Manassas Gap Railroad and 2,600 cavalry patrolled the region. Jackson was in a perfect position to pick apart Banks’ scattered army.

From Luray Jackson’s force marched north to strike the Union garrison at Front Royal commanded by Marylander Col. John R. Kenly. Because Front Royal stood between Banks’ main force near Strasburg and Union reinforcements in Fredericks-burg and also sat along the Manassas Gap Railroad (Banks’ supply line), Jackson decided to strike there first. Kenly’s defenses contained about 1,000 troops and two cannons.

By 5 a.m. on May 23 Jackson’s men were about ten miles south of Front Royal and continued to press north. As Confederate infantry marched toward Front Royal, Jackson sent his cavalry under Col. Turner Ashby to Buckton Station to disrupt lines of communication between Front Royal and Strasburg. As Jackson’s column approached Kenly’s garrison, one of Jackson’s staff officers, Henry Kyd Douglas, noticed a woman frantically trying to attract the attention of the Confederates—it was Belle Boyd. Although notorious after the Civil War for exaggerating her stories, Douglas remembered after the conflict that Boyd correctly informed Jackson about the minimal troop strength in town. Confident, Stonewall prepared to attack.

When he learned that the primary force of infantry defending the town was the 1st Maryland (U.S.), Jackson ordered his 1st Maryland (C.S.A.) to the front to lead the offensive. The Federals, grossly outnumbered and unprepared for the attack, put up little resistance in town and fled north to form a defensive position atop Richardson’s Hill. As Kenly’s men withdrew, his soldiers set fire to their camps and attempted to burn the bridges of the Shenandoah River’s South and North Forks. The wooden bridges, dampened by rain, did not ignite easily. Pursuing Confederates put out the fires on the bridge spanning the South Fork. Although not completely destroyed, the Pike Bridge across the North Fork had been damaged enough by the heroic actions of Sgt. William Taylor of the 1st Maryland (U.S.) that the Confederate advance slowed drastically. Taylor’s actions earned him the Congressional Medal of Honor.

Sensing Kenly might escape, Jackson ordered Lt. Col. Thomas S. Flournoy’s 6th Virginia Cavalry to pursue. According to various accounts, some of Flournoy’s men eased across the charred Pike Bridge in single file while others forded the North Fork. When the cavalry got to the other side they dashed on in pursuit of Kenly. Approximately three miles north of Front Royal Kenly halted his men at Cedarville and prepared to make a stand. Battle lines formed; Flournoy’s horsemen charged into their foe. Kenly’s men fired one volley that took down some of the cavalrymen, but still the Virginia horsemen galloped forward. The Union line broke under the shock of the attack. Kenly’s force was destroyed.

The fighting on May 23 was a complete success for Jackson. Stonewall’s force inflicted approximately 900 casualties on the Union force at Front Royal—more than 700 were captured. Furthermore, the Confederates seized a Union supply train, and more than $300,000 worth of supplies.  Victory came at small cost to Jackson who lost less than fifty men in the fight.

Following Confederate success at Front Royal, Gen. Banks felt uncomfortable in his position near Strasburg and withdrew north to Winchester. In the meantime Jackson, too, pushed north intent on destroying Banks’ main body.

When Banks arrived in Winchester he organized his force into a defensive position on high ground south of town. The line stretched for nearly two-and-a-half miles along the north side of Abram’s Creek—the Union left anchored near the Front Royal Road and the right stretched west of the Valley Pike to Bowers Hill. Throughout the night of May 24 Union soldiers readied themselves for a Confederate attack and gazed into the distance at the flickering fires of Jackson’s command.

Jackson’s attack commenced at daybreak on May 25. Stonewall divided his command. He took part of his force and advanced along the paved Valley Pike, while Gen. Ewell guided his men on the Front Royal Road to strike the Union left atop Camp Hill.

Gen. Isaac Trimble’s brigade attacked Camp Hill first, advancing through a heavy morning fog to be greeted by fire from Col. Dudley Donnelly’s Union brigade. Trimble’s lead regiments, the 21st North Carolina and 21st Georgia Infantry (Trimble referred to the pair as “my two 21s”) bore the brunt of the destructive fire. Initially the 28th New York and 46th Pennsylvania delivered well-aimed volleys into their attackers, but as the “two 21s” got closer, the 5th Connecticut, directly in the path of the attackers, rose, delivered a volley, and then surged forward to send Trimble’s men fleeing. With the North Carolinians and Georgians driven from the field, Trimble could not offer support as his brigade’s other two regiments, the 15th Alabama and 16th Mississippi, were not prepared to attack.

Shortly after Union troops drove Trimble’s men from Camp Hill, Jackson concluded that if his forces were to win the battle they would have to strike the western end of the Union line situated solidly atop Bowers Hill. Jackson could see Union troops moving right to the protection of a stone wall where they would be able to fire into Jackson’s left flank. Jackson knew that Bowers Hill had to be taken. At the moment the place may have seemed impenetrable—nearly one dozen artillery pieces guarded the high ground and stone and wooden fences protected Col. George H. Gordon’s infantry brigade. To crack the position Jackson turned to his old command—the Stonewall Brigade—and ordered them to take the ridge.

Gen. Charles S. Winder’s Stonewall Brigade stepped off in nearly perfect alignment. The attack went smoothly until the Confederates began to climb the slopes. As the brigade ascended the hill, a hailstorm of lead and iron from Union artillery and infantry paralyzed the attackers on the slopes of Bowers Hill. Jackson quickly determined to use a flank attack to break the position—a tactic that would soon become his trademark.

To turn Banks’ right flank Jackson chose Gen. Richard Taylor’s brigade of Louisianans. Taylor marched his men westward along Abram’s Creek to a point where it emerged in a hollow depression. There he was joined by two regiments from Gen. William Taliaferro’s brigade. The Confederate force readied itself for the attack, all the while exposed to Union artillery and musket fire. As bullets and shells rained down many Confederate soldiers tried their best to avoid being struck. When Taylor noticed some men dodging the fire he yelled profanities at them, condemning their behavior. Jackson, who was nearby, heard the cursing, glared in a disapproving manner, and told Taylor he was a wicked fellow.

With artillery support Taylor’s men surged forward. The attack commenced at approximately 7:30 a.m. and gathered momentum. As Taylor’s men bore down on the Union right flank, Banks’ cavalry struck Taylor’s left; however, Lt. Col. Francis T. Nicholls’ 8th Louisiana Infantry repulsed the Union horsemen. Soon other Confederate soldiers joined in the attack, forcing Banks’ soldiers to take to their heels and flee for safety.

While the rout of Union forces developed on Jackson’s left, Ewell finally broke the left end of the Union line on Camp Hill. By 8:30 a.m. Jackson had defeated Banks’ army.

As frightened Union soldiers retreated north through the streets of Winchester, some of the Confederate townspeople, according to Union accounts, took well-aimed shots at the fleeing soldiers. Joining the retreat were some of Winchester’s Union sympathizers who did not want to be subjected to a Confederate occupation. On the heels of the withdrawing Union troops were Jackson’s men. As Confederate soldiers streamed through the streets many joyous townspeople came out to greet them. At times the crowds of people cheering Jackson’s command became so large that Confederate soldiers had to hold their fire to avoid injuring innocent bystanders.

Once the Confederate soldiers pushed through the throngs in Winchester’s streets, they pursued Banks’ force to Stephenson’s Depot, north of town. After reaching Stephenson’s, the pursuit halted. With his infantry and artillery exhausted and an insufficient cavalry pursuit force, Jackson lost the opportunity to annihilate Banks. After the battle Jackson’s army set up camp five miles north of town. The remnants of Banks’ force marched twenty-two miles north to Martinsburg. Although able to escape, Banks lost nearly one third of his force—approximately 2,000 casualties. He also lost a tremendous amount of military stores including 500,000 rounds of ammunition, more than 100 cattle, and nearly 15,000 pounds of bacon. Jackson’s losses were considerably less—approximately 400 casualties.

The casualties inflicted on Banks and the supplies captured were little consolation to Jackson who wanted to destroy Banks’ army. But it was not meant to be. Three days after the battle Jackson received orders to move to Harper’s Ferry and give the impression that his army might march into Maryland or attack Washington, D.C. When Jackson’s army departed, only one regiment—the 21st Virginia—remained to garrison Winchester and take care of Union prisoners of war. Three days later, on May 31, no Confederates occupied Winchester. On that day Jackson withdrew south to prevent being captured in the lower Shenandoah Valley by two Union forces—Gen. James Shields advancing from the east and Gen. John C. Frémont from the west.

Even though Jackson was unable to crush Banks at Winchester and had to abandon the town less than one week after taking it, Jackson’s victory at First Winchester greatly benefited Confederates under Gen. Joseph E. Johnston who were defending Richmond from Gen. George B. McClellan’s push on the Confederate capital via the Virginia peninsula. After Winchester, President Lincoln and Secretary of War Edwin Stanton recalled Gen. Irvin McDowell’s force, which at the moment was beginning to move on Richmond via Fredericksburg to link with McClellan, so that it could take position near Manassas to protect Washington.

First Winchester had achieved tactical as well as strategic objectives. Jackson’s victory in the lower Valley caused celebration among Confederate troops defending Richmond. Four days after First Winchester, Gen. Johnston issued General Orders No. 58 celebrating Jackson’s victories at Front Royal and Winchester.

Jackson’s victories were splendid, but his work was not yet done. Two Federal armies—under Generals Frémont and Shields—still loomed on the horizon. He would deal them crushing blows at Cross Keys and Port Republic in early June, capping off his near mythical Shenandoah Valley Campaign of 1862.

About the Author:

Jonathan A. Noyalas is a history professor at Shenandoah University in Winchester. He has published more than twenty articles, essays, and reviews in publications including America’s Civil War, Blue & Gray, and the Encyclopedia of African American History (ABC-CLIO). He is the author of Plagued by War: Winchester, Virginia, During the Civil War and “My will is absolute law”: A Biography of Union General Robert H. Milroy.

This article is included in the Shenandoah Valley Battlefields Foundation’s booklet, “If this Valley is lost, Virginia is lost!”: Stonewall Jackson’s Valley Campaign.  Copies of the booklet are available at most visitor centers and many bookstores in the Valley, or in the online bookstore on CivilWarTraveler.com.