October 18, 1864 – Major General Philip Sheridan went to attend a conference in Washington, while Lieutenant General Jubal Early’s Confederates prepared to launch a surprise attack on Sheridan’s army.
As the Federal Army of the Shenandoah withdrew to Woodstock, Sheridan’s cavalry, commanded by Major General Alfred T.A. Torbert, fought rear guard actions against Early’s Confederate troopers. Disapproving Torbert’s order not to confront the Confederates, Sheridan directed him, “Either whip the enemy or get whipped yourself.”
Torbert complied, ordering two of his divisions under Brigadier Generals Wesley Merritt and George A. Custer to turn and face the opposing Confederate divisions led by Brigadier Generals Lunsford Lomax and Thomas L. Rosser (a former West Point classmate of Custer’s). Merritt pushed back Lomax’s undersized force on the left, while Custer’s 2,500 troopers took on Rosser’s 3,500 posted on hills along the south bank of Tom’s Brook, near Woodstock.
As Merritt continued pushing Lomax back, Custer traded artillery fire in Rosser’s front while shifting his men to attack the Confederate left. The unsuspecting Confederates immediately broke; according to Custer:
“The enemy, seeing his flank turned and his retreat cut off, broke in the utmost confusion and sought safety in headlong flight. The pursuit was kept up at a gallop by the entire command for a distance of nearly two miles, where a brigade of the enemy was formed to check our farther advance.”
With Rosser’s force broken, Lomax’s soon broke and ran as well. The Federals took some 300 prisoners and 11 guns (or 36 total since September 19th) as the Confederates fled 26 miles back to Early’s lines north of New Market. Federals nicknamed this fight the “Woodstock Races” as a response to the “Buckland Races” that Major General Jeb Stuart had inflicted on Custer the previous year. Custer wrote triumphantly:
“Never since the opening of this war had there been witnessed such a complete and decisive overthrow of the enemy’s cavalry. The pursuit was kept up vigorously for nearly twenty miles, and only relinquished then from the complete exhaustion of our horses and the dispersion of our panic-stricken enemies.”
Despite having his cavalry routed, Early still intended to take the offensive against Sheridan. He wrote to General Robert E. Lee, commanding the Confederate Army of Northern Virginia at Petersburg, explaining his intentions and stating, “I think I can defeat his infantry and thwart his movements…” However, Early acknowledged that he might have trouble obtaining supplies now that the Federals had laid waste to much of the upper Valley.
Meanwhile, Sheridan’s forces continued falling back northward “down” the Valley, closer to their supply lines. They crossed Cedar Creek on the 10th, just north of Strasburg. The Federals set up strong positions on either side of the Valley Turnpike, unaware that Early planned to attack. Sheridan even detached Major General Horatio G. Wright’s crack VI Corps to return to the Army of the Potomac at Petersburg.
By the 13th, Early’s Confederates had advanced to Fisher’s Hill, about five miles south of Sheridan. Despite being reinforced by Major General Joseph B. Kershaw’s infantry division, Early’s Army of the Valley was still outnumbered two-to-one. Nevertheless, a part of his force advanced and drove off Federal skirmishers before returning to Fisher’s Hill. More probing on both sides took place over the next two days.
Sheridan reacted to these probes by recalling Wright’s corps, which had stopped at Ashby’s Gap. Sheridan planned to attack Early on the 14th, but the Confederates had fallen back to strong positions on Fisher’s Hill, so Sheridan instead put Wright in command of his army and accepted a summons by Chief of Staff Henry W. Halleck to come to Washington for a strategy conference.
While preparing to leave, Sheridan learned that Federals had intercepted and deciphered a message supposedly from Lieutenant General James Longstreet, who had recently recovered from wounds suffered at the Wilderness. The message was intended for Early: “Be ready to move as soon as my forces join you, and we will crush Sheridan.”
Sheridan believed this was a bluff, but as a precaution he called off a cavalry raid into the Blue Ridge and placed those men on his right flank. Wright assured Sheridan, “I shall hold on here until the enemy’s movements are developed, and shall only fear an attack on my right, which I shall make every precaution for guarding against and resisting.”
Before his train left, Sheridan warned Wright, “Look well to your ground and be well prepared. Get up everything that can be spared.” Sheridan left with his entire cavalry corps, assuring Wright that he would return in two days, “if not sooner.”
Sheridan conferred with Halleck and Secretary of War Edwin M. Stanton in Washington on the 18th. Sheridan convinced them to approve his plan to take up defenses in the lower (northern) Valley and send VI and XIX corps back to the Army of the Potomac at Petersburg. He left the capital that day, traveling by train to Martinsburg and then by horse to Winchester, about 15 to 20 miles from his army.
Meanwhile, Confederates spied the Federal positions from atop the Shenandoah Peak and the Massanutten Mountain. They saw Sheridan’s three corps spread out along Cedar Creek’s east bank, not suspecting an attack. Being outnumbered, Early could not launch a frontal assault, but his officers informed him that the Federal left was vulnerable to a flank attack.
On the afternoon of the 18th, Early held a council of war and resolved to launch a full-scale attack at dawn. Major General John B. Gordon began the operation that night by leading three divisions around Massanutten Mountain and across the North Fork of the Shenandoah River so they could assault the Federal left in the morning. Early would then deploy Kershaw’s division to support Gordon and his fifth division with 40 guns under Major General Gabriel Wharton to hit the Federal center along the Valley Turnpike.
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