Union Major General Nathaniel P Banks learned on May 24th 1862 that his garrison at Front Royal, Virginia had fell to the Confederates. He also learned that Jackson was moving on his position. Banks made a retreat from Strasburg, with columns being attacked at Middletown and Newtown. The Confederates captured a great deal of supplies and wagons, so that they began calling Union General Banks, “Commissary Banks”.
Bank deployed at Winchester placing Union Colonel George Henry Gordon’s brigade on the right at Bower’s Hill with his left on the Valley Pike. The center of the line was held with artillery and Cavalry. Colonel Dudley Donnelly’s brigade on the Front Royal Pike covered the left with the rest of the artillery. At first light Confederate skirmisher advanced and drove the Union pickets back into their lines.
During the night Confederate Major General Richard S Ewell advanced his division. Jackson moved three of Ewell’s brigades to advance on Valley Pike, leaving just Isaac Trimble’s brigade. At dawn on May 25th 1862 Jackson had Trimble advance on the Union left flank. Trimble’s lead regiment the 21st North Carolina came under heavy fire, they regrouped and brought up artillery. Ewell advanced, sending regiment around enfilading the Union position. Donnelly withdrew back through the town.
As Ewell’s troops advanced on the Front Royal Pike, Jackson moved on the Valley Pike. He sent a brigade over the hill to the left of the Pike driving the Union skirmishers in. Jackson placed artillery and they began a duel with the Union guns on Bower’s Hill. With more Confederate troops brought up, they flanked the Union right. Although the Union troops put up a determined fight they gave way and retreated back into Winchester.
After being routed at Winchester, Banks made a retreat to the Potomac River, crossing it at Williamsport. The Confederate pursuit was sluggish at best, as Jackson’s troops were worn from hard marching done the preceding week.