Civil War Profiles: Lee’s shadowy invasion through the Shenandoah Valley

Gen. Robert E. Lee’s Army of Northern Virginia and Maj. Gen. Joseph Hooker’s Army of the Potomac were operating in a cat-and-mouse mode on their march northward away from the Rappahannock River in early June 1863. Hooker was in pursuit of Lee, who was making every effort to avoid detection of his planned invasion of the North (see “Here come the Rebels!” Coastal Point, June 10, 2014).

Soon, however, disregarded orders and bureaucratic incompetence led to the fall of the Union garrison at Winchester, in the Shenandoah Valley of Virginia. Lt. Gen. Richard S. Ewell orchestrated the Confederate victory on June 15, 1863, while there was plenty of blame to go around for the Union defeat that resulted in 4,500 casualties — mostly captured soldiers.

Cavalry leader Brig. Gen. Alfred Pleasonton had not followed Hooker’s orders to reconnoiter the Shenandoah Valley for evidence of an invasion. That was compounded when military officials in Washington and Baltimore were not in sync with Maj. Gen. Robert H. Milroy, commander of the Union outpost in Winchester, about the need to withdraw to a more defensible position at Harper’s Ferry.

To prevent Lee from organizing a surprise attack against Washington, Hooker deployed his army in an arc around the capital. On June 17, he ordered Pleasonton’s cavalry to move to “the vicinity of Aldie [Va.], and push out reconnaissances toward Winchester, Berryville and Harper’s Ferry” in search of Lee in the Valley.

Given the debacle at Winchester, Hooker emphasized to Pleasonton that he “relies upon you … to give him information on where the enemy is, his force and his movements.” He directed Pleasonton to cooperate with Col. George H. Sharpe’s intelligence staff, and allow them to interrogate “prisoners, [enemy] deserters, or contrabands [escaped slaves] brought in … [to gather] the fullest information.”

Those orders set the stage for a series of battles over the next several days between the opposing cavalry forces in Loudoun Valley, a stretch of land between the Bull Run and Blue Ridge Mountains south of the Potomac River. The Confederate cavalry commander, Maj. Gen. Jeb Stuart, wanted to prevent Pleasonton from observing Lee’s army as it marched northward down the Shenandoah Valley on the other side of the Blue Ridge.

Lee’s army of more than 70,000 was making its way over a 100-mile-long stretch from Culpeper Court House in Virginia to above the Potomac River in Maryland. To screen this movement from the eyes of the enemy, Stuart adopted a defensive strategy, slowly withdrawing from ridge to ridge, resisting the enemy’s attempt to reach the mountains and observe the movement.

As described in Robert F. O’Neill Jr.’s account, the fighting was intense through the towns of Aldie, Middleburg and Upperville.

Meanwhile, Brig. Gen. Albert Jenkins’ cavalry brigade, the vanguard of Lee’s army, had crossed the Potomac into Maryland, and was gathering foodstuffs and livestock from surrounding farms — shipping them south for current and future use by the army.

Edward G. Longacre wrote in “The Cavalry at Gettysburg” that, ominously, a Confederate objective was the capture of “fugitive” blacks and sending them back into slavery. Under those hectic conditions, however, many free blacks fell prey, along with escaped slaves.

Lee also lacked knowledge of the Army of the Potomac’s position and plans. That changed on June 18, when Maj. John S. Mosby’s rangers captured couriers carrying dispatches that disclosed the Union army’s general location and basic strategy.

In another effort to obtain information about Lee’s army, on June 20, Hooker ordered Sharpe to send an agent into Maryland to determine if Lee had crossed the Potomac. For the mission, Sharpe selected John Babcock, a civilian intelligence specialist with field experience and a thorough knowledge of the organization and strength of Lee’s forces. His destination was Frederick, Md., to set up an observation post on South Mountain, looking southwest toward the Potomac River.

From there, Babcock would be in position to observe the bulk of Lee’s army crossing the river, when and if that should occur. Once he felt confident that Lee was headed for Pennsylvania, Hooker planned to move away from the defense of Washington and head northward in pursuit.

At that stage of the campaign, neither side had gained the upper hand. However, as we shall see, Lee’s approval of a risky maneuver that cavalry commander Stuart proposed would have far-reaching effects on the outcome of the Confederate invasion of the North.

Bethany Beach resident Thomas J. Ryan is the author of “Essays on Delaware during the Civil War: A Political, Military and Social Perspective” (available at Bethany Beach Books or from his website at Contact him at