Major-General Joseph Hooker, commanding the Federal Army of the Potomac, sent part of his force marching north on the morning of June 11. These troops were in pursuit of General Robert E. Lee’s Confederate Army of Northern Virginia, which was headed for the Shenandoah Valley. The Federals pursued but stayed on what President Abraham Lincoln called the “inside track.”
Hooker was required to keep his army between Lee in his front and Washington in his rear, even though he still did not know Lee’s exact location. The Bureau of Military Information, which had been so effective in estimating enemy strength for Hooker at Fredericksburg, had a much more difficult time doing so when the Confederates were on the move. And Brigadier-General Alfred Pleasonton, head of the Federal Cavalry Corps, was proving inept at providing enemy intelligence. As Hooker moved, he was doing so blindly, and most of his army remained in its camps at Falmouth.
Meanwhile, the Confederates continued their march to the northwest. The only substantial obstacle in their path was Major-General Robert H. Milroy’s 6,900-man Federal division, which had been guarding Winchester and Harpers Ferry since January. This force was part of the Middle Department, commanded by Major-General Robert C. Schenck in Baltimore. Schenck 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, “I have sufficient force to hold the place safely, but if any portion is withdrawn the balance will be captured in 48 hours.”
Back at Falmouth, Hooker continued receiving various reports from cavalry, scouts, and observation balloons on the positions of Lee’s army. But some of these reports conflicted. Hooker wrote Halleck on the 12th, “It is reported to me from the balloon that several new rebel camps have made their appearance this morning. There can be no doubt but that the enemy has been greatly re-enforced.” That afternoon, Hooker wrote Major-General John A. Dix, commanding at Fort Monroe on the Virginia Peninsula between the York and James rivers:
“All of Lee’s army, so far as I know, is extended along the immediate bands of the Rappahannock, from Hamilton’s Crossing (south of Fredericksburg) to Culpeper. A.P. Hill’s corps is on his right, below Fredericksburg. (Richard) Ewell’s corps joins his left, leading to the Rapidan; and beyond that river is (James) Longstreet’s corps, with not less than 10,000 cavalry, under (Jeb) Stuart… From my balloon it can be seen that he is daily receiving acquisitions. He has a numerical superiority over me.”
Pleasonton reported to Hooker, “I am inclined to believe they will not send off their cavalry or make a move until they are satisfied of ours. The information I receive is that they will play the defensive until we make a false step.”
But Lee’s army was not on the defensive; it was still marching toward the Shenandoah Valley. The vanguard, consisting of Lieutenant-General Richard Ewell’s Second Corps, was moving through Chester Gap in the Blue Ridge on the 12th. Lee had selected Ewell to lead the way due to Ewell’s strong performance in Thomas “Stonewall” Jackson’s legendary Shenandoah campaign in 1862. Ewell was to clear a path for the rest of the army into Maryland.
The Federal occupation forces in the Valley consisted of three forces: Colonel Andrew T. McReynolds’s 1,800-man brigade at Berryville, Brigadier-General Benjamin F. Kelley’s command at Harpers Ferry, and Milroy’s at Winchester. None had seen anything more than Confederate cavalry and therefore did not know a Confederate army was heading their way.
Milroy assured Schenck that Winchester could be held, prompting Schenck to reply, “Be ready, but wait for further orders.” Milroy was to “make all the required preparations for withdrawing,” but stay put unless ordered to leave. Milroy guessed the Confederates would come at some point, writing 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. A servant who had escaped from Lee’s army informed Captain John McEntee, part of Federal intelligence, that the Confederates were headed for the Shenandoah, with Ewell in the lead and Lieutenant-General James Longstreet’s First Corps following. McEntee reported, “I think statement reliable.”
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