Lieutenant General Richard Ewell pushed his men of the Second Corps northward from Culpeper Court House on June 10 on a march that would have made even Stonewall Jackson proud. His foot cavalry entered the Shenandoah Valley via Chester Gap on June 12; Ewell led the way in a carriage. This was his first campaign since losing a leg at Groveton during the Second Manassas Campaign and by June 12, he was simply worn out.
After conferring with his three division commanders that evening, Ewell crafted a plan to clear the Federal forces out of the lower Shenandoah Valley. Robert Rodes’ Division would march to Berryville accompanied by Albert Jenkins’ cavalry brigade. Once there, he would capture the 1,800 men of Col. Andrew McReynolds’ brigade of Maj. Gen. Robert Milroy’s division. After reducing Berryville, Rodes and Jenkins would turn their attention to Col. Benjamin Smith’s command of 1,300 men guarding the Baltimore and Ohio Railroad at Martinsburg. Ewell’s other two divisions under Early and Johnson would attack Milroy’s main body of approximately 8,000 men at Winchester. Johnson would march on the Front Royal Road toward Winchester while Early turned west at Nineveh and marched to Newtown, where his division would pick up the Valley Turnpike. Ewell was going to strike Winchester from two directions.1
Despite frequent requests from Henry Halleck to vacate Winchester and head toward Harpers Ferry, Milroy had thus far refused. He believed his command occupied good defensive positions and could repel any Confederate attack. He did not know that more than twelve thousand men were bearing down on him, intent on his destruction.
The first clash between Milroy’s and Ewell’s troops occurred on the morning of June 12 when a Federal cavalry patrol encountered Johnson’s Division south of Winchester. The patrol quickly alerted Milroy, who rushed reinforcements to the area—about 600 men from the 87th Pennsylvania, 18th Connecticut, and 13th Pennsylvania Cavalry, along with a section of Spooner’s battery. Milroy intended to lay a trap for the approaching enemy of the 1st Maryland Battalion and the 14th Virginia Cavalry. The latter fell into the snare, losing about 50 men.2
Milroy was still in denial that night about his circumstances. “I deemed it impossible that Lee’s army, with its immense artillery and baggage trains, could have escaped from the Army of the Potomac, and crossed the Blue Ridge,” he wrote. Although Milroy was skeptical that the enemy was approaching in great force, he disposed his troops to defend the town. He doubled the number of pickets and ordered Col. McReynolds to return with his brigade to Winchester if he heard two cannon shots. He also deployed parts of his remaining two brigades in positions to guard the Valley and Front Royal turnpikes. To the former, commanded by Brig. Gen. Washington Elliott, went the 110th and 123rd Ohio, 12th West Virginia, 13th Pennsylvania Cavalry, and John Carlin’s Battery D. Colonel William Ely took his brigade, composed of the 87th Pennsylvania, 18th Connecticut, 5th Maryland, 12th Pennsylvania Cavalry, and a section of E. D. Spooner’s Battery L, south along the Fort Royal Turnpike.3
Ewell’s plan for defeating Milroy was remarkably similar to Stonewall Jackson’s design during his First Winchester Campaign one year earlier—and it was to Ewell’s advantage that he had participated in it. Johnson’s Division would advance up the Front Royal Turnpike in full view of Milroy’s soldiers while Early’s Division left the Valley Turnpike, looped around to the left, and hit Milroy’s fortifications from the west. “From all of the information I could gather,” explained Ewell, “the fortifications of Winchester were only assailable from the west and northwest." It was a good plan, and one made more likely to succeed by Milroy’s blind determination.4