Published on June 9, 2015

By the late summer of 1864, the Union had experienced the disaster at Kernstown and the Confederate burning of Chambersburg.  Gen. Ulysses S. Grant resolved to crush Confederate Gen. Jubal Early’s army and destroy the fertile Shenandoah as a military granary for Lee’s army.

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He reorganized several military districts under one commander and chose his aggressive cavalryman, Gen. Philip H. Sheridan, to lead this new army with the bulk of the Federal cavalry. Sheridan’s instructions were to defeat Early and conduct a campaign of total warfare in the Valley.  After an initial period of “mimic war,” Sheridan delivered a series of stinging defeats.Sheridan took command at Harper’s Ferry on August 7.  Early deployed his forces to defend the approaches to Winchester, while Sheridan moved his army, now 50,000 strong, south via Berryville with the goal of cutting the Valley Turnpike. On August 11, Confederate cavalry and infantry turned back Union cavalry at Double Toll Gate in sporadic, day-long fighting, preventing this maneuver

Gen. George A. Custer

Robert E. Lee sent reinforcements under the overall command of Gen. Richard Anderson to join Early. On August 16, Union cavalry encountered this force advancing through Front Royal, and in a sharp engagement at Guard Hill, Gen. George A. Custer’s brigade captured more than 300 Confederates.

Sheridan had been ordered to move cautiously and avoid a defeat, particularly if Early were reinforced. Uncertain of Early’s and Anderson’s combined strength, Sheridan withdrew to a defensive line near Charles Town to cover the Potomac River crossings and Harpers Ferry. Early’s forces routed the Union rear guard at Abrams Creek at Winchester on August 17 and pressed north on the Valley Turnpike to Bunker Hill. Judging Sheridan’s performance thus far, General Early considered him a timid commander.

On August 21, Early and Anderson launched a converging attack against Sheridan. As Early struck the main body of Union infantry at Cameron’s Depot, Anderson moved north from Berryville against Sheridan’s cavalry at Summit Point. Results of the fighting were inconclusive, but Sheridan continued to withdraw. The next day, Early advanced boldly on Charles Town, panicking a portion of the retreating Union army, but by late afternoon, Sheridan had retreated into formidable entrenchments at Halltown, south of Harpers Ferry, where he was beyond attack.

Early then attempted another incursion into Maryland, hoping by this maneuver to maintain the initiative. On August 25, two divisions of Sheridan’s cavalry intercepted Early’s advance, but the Confederate infantry drove them back to the Potomac. Early’s intentions were revealed, however, and on August 26, Sheridan’s infantry attacked and overran a portion of the Confederate entrenchments at Halltown, forcing Anderson and Kershaw to withdraw to Stephenson’s Depot. Early abandoned his raid and returned south, establishing a defensive line on the west bank of Opequon Creek from Bunker Hill to Stephenson’s Depot.

On September 2-3, Averell’s cavalry division rode south from Martinsburg and struck the Confederate left flank at Bunker Hill, defeating the Confederate cavalry but being driven back by infantry. Meanwhile, Sheridan concentrated his infantry near Berryville. On the afternoon of September 3, Anderson’s command encountered and attacked elements of Crook’s corps (Army of West Virginia) at Berryville but was repulsed. Early brought his entire army up on the 4th, but found Sheridan’s position at Berryville too strongly entrenched to attack. Early again withdrew to the Opequon line.

On September 15, Anderson left the Winchester area to return to Lee’s army and by the 18th had reached the Virginia Piedmont. Early spread out his remaining divisions from Winchester to Martinsburg, where he once more cut the B&O Railroad. When Sheridan learned of Anderson’s departure and the raid on Martinsburg, he determined to attack at once while the Confederate army was scattered


On September 19, Sheridan advanced his army on the Berryville Turnpike, precipitating the battle of Third Winchester (Opequon).  By forced marches, Early concentrated his army in time to intercept Sheridan’s main blow. The battle raged all day on the hills east and north of Winchester. Early’s veterans decimated two divisions of the XIX Corps and a VI Corps division in fighting in the Middle Field and near the Dinkle Barn. Confederate division commander Gen. Robert E. Rodes and Union division commander Gen. David A. Russell were killed within a few hundred yards of one another in the heat of the fighting. Late in the afternoon a flanking movement by Crook’s corps and the Union cavalry finally broke Early’s overextended line north of town. Third Winchester was a do-or-die effort on the part of both armies, resulting in nearly 9,000 casualties

Sheridan’s victory was decisive but incomplete; Early retreated twenty miles south to his entrenchments at Fisher’s Hill and Sheridan followed.

Preliminary skirmishing on the 21st showed that a frontal assault would be costly, so Sheridan resorted to a flanking movement on September 22. Hidden from the Confederate signal station on Massanutten Mountain by the dense forest, Crook’s two divisions marched along the shoulder of Little North Mountain to get behind the Confederate lines. In late afternoon, Crook’s soldiers fell on Early’s left flank and rear “like an avalanche,” throwing the Confederate army into panicked retreat. At Milford (Overall) in the Luray Valley on the same day Confederate cavalry prevented two divisions of Union cavalry from reaching Luray and passing New Market Gap to intercept Early’s defeated army as it withdrew up the Valley.

Gen Jubal A. Early

Early retreated to Rockfish Gap near Waynesboro, opening the Valley to Union depredations and what came to be known as The Burning, a two-week campaign of destruction to neutralize the agricultural base of the Valley – the “Breadbasket of the Confederacy.”  After convincing Grant that he could proceed no farther than Staunton, Sheridan withdrew down the Valley, systematically burning mills, barns, and public buildings, destroying or carrying away the forage, grain, and livestock. During this portion of the campaign, Confederate partisan groups under John S. Mosby and Harry Gilmor increased their activities against Union supply lines in the Lower Valley.

Sheridan thought he had destroyed Early’s army, but Kershaw’s division and another brigade of cavalry were returned to the Valley, nearly making up the losses suffered at Opequon and Fisher’s Hill.  Early followed Sheridan’s withdrawal, sending his cavalry under Gen. Thomas L. Rosser to harass the Union rear guard. Angered by Rosser’s constant skirmishing, Sheridan ordered his commander of cavalry, Gen. Alfred T. Torbert, to “whip the enemy or get whipped.”  On October 9, Torbert unleashed the divisions of his young generals, Wesley Merritt and George Custer, on the Confederate cavalry, routing it at Tom’s Brook. In the melee that followed, victorious Union troopers chased the Confederates twenty miles up the pike and eight miles up the Back Road, in what came to be known as the “Woodstock Races.” The morale and efficiency of the Confederate cavalry were seriously impaired for the rest of the war.

Gen. Philip H. Sheridan
Gen. Philip H. Sheridan

On October 13, Early reoccupied Fisher’s Hill and pushed through Strasburg to Hupp’s Hill where he engaged a portion of Sheridan’s army. When Sheridan realized the proximity of Early’s forces, he recalled the VI Corps, which had again been dispatched to join Grant. On October 19, at dawn, after an unparalleled night march, Confederate infantry directed by Gen. John B. Gordon surprised and overwhelmed the soldiers of Crook’s corps in their camps at Cedar Creek. The XIX Corps suffered a like fate as the rest of Early’s army joined the attack. Only the VI Corps maintained its order as it withdrew beyond Middletown, providing a screen behind which the other corps could regroup.

Sheridan, who was absent when the attack began, arrived on the field from Winchester and immediately began to organize a counterattack, saying “if I had been with you this morning, boys, this would not have happened.” In late afternoon, the Union army launched a coordinated counterattack that drove the Confederates back across Cedar Creek. Sheridan’s leadership turned the tide, transforming Early’s stunning morning victory into afternoon disaster. Early retreated up the Valley under sharp criticism of his generalship, while President Abraham Lincoln rode the momentum of Sheridan’s victories in the Valley and Sherman’s successes in the Atlanta campaign to re-election in November.

Sheridan's Ride

The story of Sheridan’s campaign resonates in Valley families even today. Indeed, this history is especially compelling—not only because of its effect on the eventual outcome of the Civil War—but also because of its impact on the personal lives of the Shenandoah’s citizenry.

There are many places in the Valley that today tell the story of this dramatic campaign, from mill sites to battlefields to museums. As you explore the Valley, you may even encounter a resident who might share with you his or her own family’s experience during this dark chapter of the Valley’s history.


Guard Hill (August 16)
Berryville (Sept. 3-4)
Third Winchester (Opequon) (Sept. 19)
Fisher’s Hill (Sept. 22)
Tom’s Brook (Oct. 9)
Cedar Creek (Oct. 19)