June 12, 1863 – Part of the Confederate Army of Northern Virginia drove toward Winchester on its way to the Potomac River and the North.
As the Confederates continued their march toward the Shenandoah Valley, the only substantial obstacle in their path was Major General Robert H. Milroy’s 5,100-man Federal division, which had guarded Winchester and Harpers Ferry since January. This force was part of Major General Robert C. Schenck’s Middle Department. Schenck, headquartered at Baltimore, warned Milroy to be on alert and prepare to defend Harpers Ferry against a potential attack, even if it meant abandoning Winchester.
Milroy was extremely unpopular among the people of Winchester because of his dictatorial rule. He destroyed buildings and houses to build fortifications, he arrested anyone expressing Confederate sympathies, he freed local slaves (prompting Virginia Governor John Letcher to offer a $100,000 reward for his capture or execution), and he seized private homes to shelter his troops. Even many Unionists had turned against Milroy due to his harsh tactics.
Milroy told Schenck that abandoning Winchester would not be necessary because he had built defenses there that could withstand any Confederate assault. One of Schenck’s aides inspected the defenses and reported that the Federals “can whip anything the rebels can fetch here.” Milroy asserted, “I can and would hold it, if permitted to do so against any force the rebels can afford to bring against me, and I exceedingly regret the prospect of having to give it up…”
General-in-Chief Henry W. Halleck, who saw no benefit in holding Winchester, wrote Schenck:
“Harpers Ferry is the important place, Winchester is of no importance other than as a lookout. The Winchester troops, except enough to serve as an outpost, should be withdrawn to Harpers Ferry.”
The message was forwarded to Milroy with an attachment: “It must be considered an order, and obeyed accordingly. Take immediate steps. You understand this.” Milroy replied on the 11th, “I have sufficient force to hold the place safely, but if any portion is withdrawn the balance will be captured in 48 hours.”
Meanwhile, the vanguard of the Confederate army, Lieutenant General Richard Ewell’s Second Corps, continued moving toward Winchester, reaching the eastern edge of the Blue Ridge that day and crossing on the 12th. Ewell planned to divide his 13,000 men by sending part to take Colonel Andrew T. McReynolds’s 1,800-man Federal brigade at Berryville and part to take Milroy’s garrison at Winchester.
Although Halleck had urged Milroy to withdraw to Harpers Ferry, Milroy insisted that his Federals could hold Winchester. Schenck, after receiving Milroy’s assurance that Winchester could be held, wired him, “Be ready, but wait for further orders.” Milroy was to “make all the required preparations for withdrawing,” but stay put unless ordered to leave.
Of the three Federal commands in the Shenandoah Valley (Milroy’s at Winchester, McReynolds’s at Berryville, and Brigadier General Benjamin F. Kelley’s at Harpers Ferry), none had seen anything more than Confederate cavalry and therefore did not know a Confederate army was heading their way. But Milroy guessed they would come at some point, wiring Schenck, “The enemy are probably approaching in some force. I am entirely ready for them. I can hold this place.”
Milroy explained that holding Winchester was vital to secure the Baltimore & Ohio Railroad, guard Unionists in the region, and protect nearby foodstuffs being harvested for the troops. The fortifications outside the town made Milroy confident that “I can hold them against five times my number.” Based on this, Milroy wrote, “I am, therefore, decidedly of the opinion that every dictate of interest, policy, humanity, patriotism, and bravery requires that we should not yield a foot of this country up to the traitors again.”
By day’s end, Ewell’s Confederates had marched through Chester Gap and camped north of Cedarville, less than 20 miles from Winchester. The next morning, Ewell’s cavalry under Brigadier General Albert G. Jenkins and one of his infantry divisions under Major General Robert Rodes struck out for Berryville, while Ewell’s other two divisions under Major Generals Edward “Allegheny” Johnson and Jubal Early headed to Winchester, 12 miles east of Berryville.
Rodes hoped to take McReynolds by surprise, but a Federal picket had already alerted him of the Confederates’ approach. Rodes dispatched Jenkins’s cavalry to pursue the withdrawing garrison, but the troopers could not catch the Federals before they joined Milroy at Winchester. McReynolds, having only seen enemy cavalry during his withdrawal, still did not know that Confederate infantry was approaching.
At Harpers Ferry, Kelley heard rumors that the Confederates had destroyed all available supplies at Berryville. He wrote, “If this is reliable, it would seem as if it was not a movement in force” because an advancing army would need those supplies.
Meanwhile, Johnson drove in Federal outposts south of Winchester, while Early moved to confront the fort west of town. Skirmishing occurred until nightfall, when Milroy learned from a Confederate prisoner that his Federals were facing Ewell’s corps. He wrote Schenck, “I can hold this place five days if you can relieve me in that time. They will surround, but can’t take, my fortifications.”
Schenck ordered Milroy to abandon Winchester, but the message did not get through due to downed telegraph wires.
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