As Southern units retreated and resistance fell apart, Northern victory was assured.
Jackson found himself surrounded by a disorderly retreat of his soldiers. In the growing dark, a few fresh Southern units made gallant attempts to cover the Southern retreat from Northern pursuit. One group formed a defensive square until they were completely surrounded and had to surrender. In the fields where you now stand, Northern horsemen gathered up approximately 250 wounded and retreating Southern troops, among them Jackson's brother-in-law and Sgt. Major Randolph Barton of the 33rd Virginia.
That night Jackson camped the disorganized remnants of his army just south of Newtown (now Stephens City) along the Valley turnpike. His men had, within two days, marched forty miles and fought a battle against superior numbers. Jackson's own performance had been less than exemplary. He had risked his army by pitching it headlong into a larger Northern force without an adequate picture of enemy strength. He failed to rely on his subordinates and communicate his battle plan to them. Finally, Jackson chose to fight this battle from the rear, feeding his units into the fight rather than being at the front and controlling the action. He would not make the same mistake again.
Kate Sperry, a young woman from Winchester, visited several days after the battle. In her diary she described what she saw.
"...we walked over a portion of it - where the fight was the thickest... the trees were scarred all over and branches shot off by the balls - the ground discolored by the blood of our men and Yanks also. I got a bullet that one of the Yanks fired at our men when our men were behind the stone wall - or fence rather ... Mr. M. assisted to bury our men - 79 in a tiny trench - side by side and a rail fence around them ... it was truly sad to see them - a haversack belonging to some of our men was lying on the ground by the fence, a piece of grey blanket and an old coat, part of a red flannel shirt ... . I brought away a piece of that stone fence - am going to preserve it."
-Kate Sperry diary excerpt