September 16, 1864 – Major General Philip Sheridan unveiled a plan to drive Lieutenant General Jubal Early’s Confederates out of the Shenandoah Valley once and for all.
As September began, Sheridan’s Federal Army of the Shenandoah began coming out of its defenses and moving down the Valley Turnpike toward Winchester. Early’s Army of the Valley blocked Sheridan at Bunker Hill, north of Winchester. The Confederates were reinforced by elements of Lieutenant General Richard H. Anderson’s corps from General Robert E. Lee’s Army of Northern Virginia.
Both sides maneuvered and skirmished, with Early’s main force setting up at Stephenson’s Depot and Sheridan’s moving east of Winchester, between Berryville and Clifton. No major confrontation seemed imminent, so Anderson’s Confederates began heading east toward Snicker’s Gap; from there they were to move through the Blue Ridge and return to Lee’s army at Petersburg.
Anderson’s lead division under Major General Joseph B. Kershaw advanced toward Berryville, unaware that Sheridan had stationed Brigadier General George Crook’s VIII Corps there. The two forces collided near sunset on the 3rd. The Federals fell back but then regrouped and counterattacked. Kershaw disengaged for the night, and Early came up with three reinforcing divisions the next day. But as Early wrote after the war:
“I at first thought that I had reached his (Sheridan’s) right flank, and was about making arrangements to attack it, when casting my eye to my left, I discovered, as far as the eye could reach with the aid of field glasses, a line extending toward Summit Point. The position the enemy occupied was a strong one, and he was busily engaged fortifying it, having already made considerable progress. It was not until I had this view that I realized the size of the enemy’s force, and as I discovered that his line was too long for me to get around his flank, and the position was too strong to attack in front, I returned and informed General Anderson of the condition of things.”
The Confederates fell back west toward Winchester and took positions on high ground east of the Valley Turnpike. The Federal army doubled the size of Early’s, but Sheridan did not pursue the Confederates. This was mainly because Sheridan had to detach units to guard his supply lines, prevent raids into Maryland or Pennsylvania, and protect both the Baltimore & Ohio Railroad and the Chesapeake & Ohio Canal. Also, with the presidential election coming in two months, Sheridan did not want to risk jeopardizing Abraham Lincoln’s reelection with a defeat.
The two armies probed each other’s defenses for the next two weeks, looking for exploitable weaknesses but finding none. Lieutenant General Ulysses S. Grant, the overall Federal commander, encouraged Sheridan on the 9th:
“I would not have you make an attack with the advantage against you, but would prefer just the course you seem to be pursuing–that is, pressing closely upon the enemy, and when he moves, follow him up, being ready at all time to pounce upon him if he detaches any considerable force.”
This strategy would prevent Early’s Confederates from reinforcing Lee’s Army of Northern Virginia. But it would also allow Early to control the Valley, where his men could ensure the continued transfer of the rich harvests to Lee’s besieged forces at Petersburg.
Another three days of sparring prompted President Lincoln to write Grant: “Sheridan and Early are facing each other at a deadlock. Could we not pick up a regiment here and there, to the number of say 10,000 men, and quietly but suddenly concentrate them at Sheridan’s camp and enable him to make a strike? This is but a suggestion.” Grant replied that he intended “to see Sheridan and arrange what was necessary to enable him to start Early out of the Valley. It seems to me it can successfully be done.”
Meanwhile, Early held strong positions along Opequon Creek, and after delays, Anderson’s Confederates began leaving the Valley on the 14th to rejoin Lee, who desperately needed them on the Petersburg siege lines. That same day, Grant left Petersburg to confer with Sheridan at Charles Town.
Rumors quickly spread among Sheridan’s army that Anderson was leaving, but Sheridan informed Grant, “I have nothing new to report for yesterday or today. There is as yet no indication of Early’s detaching.” Sheridan asked his cavalry commanders to determine whether Early’s army had been weakened by Anderson’s departure. When they were slow in gathering information, Sheridan enlisted troops to serve as scouts and asked Crook if he knew of any civilians at Winchester who would be willing to provide intelligence.
Crook recommended Rebecca Wright, a Quaker teacher and known Unionist. Sheridan wrote her a letter of introduction, which was smuggled to her by a black messenger who wrapped it in tinfoil and carried it under his tongue. Wright read the message and answered: Anderson’s men and three batteries had returned to Petersburg, and Early’s reduced army was scattered around Winchester and highly vulnerable to attack.
This meant that Sheridan’s chance of defeat was greatly reduced. And news of William T. Sherman’s capture of Atlanta meant that even if Sheridan was defeated, Lincoln’s reelection bid was already gaining momentum. Sheridan therefore resolved to take the offensive, but to increase his chance of success even further, he would wait until Anderson’s Confederates were far enough away so they could not hurry back to help Early.
As Sheridan plotted his moves, Grant arrived in Charles Town and met with him at the Rutherford House. Grant had a specific plan in mind for Sheridan to drive Early out of the Valley and destroy Lee’s supply line. Worried that administration officials might reject this plan, Grant had bypassed Washington and traveled straight to Sheridan’s headquarters.
But before Grant could share his plan, Sheridan revealed one of his own. Most of his Federals would seize the Valley Turnpike at Newtown, below Winchester, while his cavalry would confront the small Confederate force in Winchester. The Federals would cut off Early’s supply lines and escape route, forcing him to fight on ground of Sheridan’s choosing.
According to Sheridan, Grant “neither discussed nor disclosed his plans, my knowledge of the situation striking him as being so much more accurate than his own.” Instead, Grant simply told Sheridan, “Go in.”
CivilWarDailyGazette.com; Denney, Robert E., The Civil War Years: A Day-by-Day Chronicle (New York: Gramercy Books, 1992 [1998 edition]), p. 452-54, 458-60; Foote, Shelby, The Civil War: A Narrative: Volume 3: Red River to Appomattox (Vintage Civil War Library, Knopf Doubleday Publishing Group, Kindle Edition, 2011), Loc 11585-616; Fredriksen, John C., Civil War Almanac (New York: Checkmark Books, 2007), p. 492-95, 497; Lewis, Thomas A., The Shenandoah in Flames: The Valley Campaign of 1864 (Alexandria, VA: Time-Life Books, 1983), p. 108-09; Long, E.B. with Long, Barbara, The Civil War Day by Day (New York: Da Capo Press, Inc., 1971), p. 564-65, 569-70; McPherson, James M., Battle Cry of Freedom: The Civil War Era (Oxford History of the United States Book 6, Oxford University Press, Kindle Edition, 1988), p. 776; Wert, Jeffry D., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 677-79