September 19, 1864 – Major General Philip Sheridan’s Federals attacked the weakened Confederate army outside Winchester as part of Sheridan’s overall effort to drive the Confederates out of the Shenandoah Valley.
Lieutenant General Jubal Early’s Confederate Army of the Valley was reduced to just 12,000 men after Lieutenant General Richard H. Anderson’s detachment left the Shenandoah to rejoin the Army of Northern Virginia at Petersburg. Despite this, Early sent two divisions under Major Generals Robert Rodes and John B. Gordon north to destroy a bridge on the Baltimore & Ohio Railroad, west of Martinsburg.
This left just 4,000 Confederates to defend Winchester and Stephenson’s Depot along Opequon Creek. Early decided to spread his army thin because Sheridan, commanding the 40,000-man Federal Army of the Shenandoah, had shown no aggression since taking command. But Early was unaware that Sheridan, having received vital intelligence from a spy named Rebecca Wright, was about to attack.
Sheridan initially planned to attack the Confederates at Winchester while cutting off the Valley Turnpike below the town. But when he learned that Early divided his army, Sheridan instead opted to destroy the force at Winchester and Stephenson’s Depot, and then move on to destroy the force west of Martinsburg. Orders were issued for the Federals to mobilize at 2 a.m. on the 19th. According to Sheridan’s plan:
- Major General Horatio G. Wright’s VI Corps would advance on the Berryville Pike, and, “As soon as it has reached open country it will form in line of battle, fronting in the direction of Stephenson’s Depot.”
- Brigadier General William H. Emory’s XIX Corps would support Wright.
- Major General George Crook’s Army of West Virginia (i.e., VIII Corps) would be in reserve, “to be marched to any point required.”
As the Federals prepared, Early learned from intercepted dispatches that Lieutenant General Ulysses S. Grant, the overall Federal commander, had recently met with Sheridan. This indicated that Sheridan might attack soon. Early therefore ordered Rodes and Gordon to stop wrecking railroad tracks and hurry back to Winchester. By the end of the 18th, Rodes was back at Stephenson’s Depot, and Gordon was at Bunker Hill. The Confederates were still spread along a 14-mile line, but they were more concentrated than they had been when the day began.
The Federals advanced at 3 a.m. on the 19th, led by the cavalry. Their initial target was Major General Stephen D. Ramseur’s isolated division on the Berryville Road, about a mile and a half east of Winchester. However, Sheridan mishandled the advance by sending his men through the narrow Berryville Canyon, and a major traffic jam ensued among the men, horses, and wagons. The delay gave Early time to bring up Rodes and Gordon from the north, and Major General John C. Breckinridge’s division from the south.
The Federals approached the Confederates on a north-south line, with Wright on the left (south) and Emory on the right. Gordon’s division came up to Ramseur’s left (north), and fighting began in the cornfields and woodlands at 11:40 a.m. One of Emory’s divisions under Brigadier General Cuvier Grover pushed Gordon back but was then repulsed by a counterattack. Gordon’s division nearly decimated XIX Corps.

The Confederates discovered a gap in the Federal center just as Rodes’s division came up, and troops from both Rodes’s and Gordon’s commands pushed through. Early wrote that it “was a grand sight to see this immense body hurled back in utter disorder before my two divisions, numbering a very little over 5,000 muskets.” But Early suffered a major loss when Rodes was mortally wounded in the assault.
Sheridan brought up the rest of VI and XIX corps to plug the gap, and Brigadier General David A. Russell, commanding a division in VI Corps, was killed by shrapnel in the counterattack. The Federals eventually closed the gap, which possibly saved the army from destruction. Sheridan later wrote:
“The charge of Russell was most opportune, but it cost many men in killed and wounded. Among the former was the courageous Russell himself, killed by a piece of shell that passed through his heart, although he had previously been struck by a bullet in the left breast, which wound, from its nature, must have proved mortal, yet of which he had not spoken. Russell’s death oppressed us all with sadness, and me particularly.”
During a lull on the field, Sheridan directed Crook’s Federals to move around the Confederate left. The Confederates crumbled under the overwhelming assault; Colonel George S. Patton (grandfather of World War II General George S. Patton) was mortally wounded and his brigade was decimated. Gordon repositioned his withdrawing men behind a stone wall on a line running east to west, perpendicular to the rest of Early’s army. Breckinridge’s division came up to extend the Confederate left flank.
Meanwhile, Wright’s Federals launched another attack on the Confederate right, as Sheridan rode along the front, waving his hat and yelling, “Give ‘em hell… Press them, General, they’ll run!” As the Federals gradually pushed the Confederates back toward Winchester, Major General Alfred T.A. Torbert’s Federal cavalry attacked Breckinridge’s isolated division on the far left until one of Early’s cavalry brigades fought them off.

Around 4:30 p.m., Crook and Wright launched assaults that broke the Confederate left and penetrated Breckinridge’s part of the line. Cavalry under Brigadier Generals Wesley Merritt and William W. Averell attacked in support. Sheridan wrote, “Panic took possession of the enemy, his troops, now fugitives and stragglers, seeking escape into and through Winchester.” Ramseur’s Confederates held off the Federals to allow an orderly retreat. This marked the first time that Early’s army had been driven from the field.
The Confederates withdrew along the Valley Turnpike to Newtown while moving their supplies, munitions, and equipment to Fisher’s Hill. Sheridan reported to Grant, “I have the honor to report that I attacked the forces of General Early on the Berryville pike at the crossing of Opequon Creek, and after a most stubborn and sanguinary engagement, which lasted from early in the morning until 5 o’clock in the evening, completely defeated him.” The Federals captured “2,500 prisoners, five pieces of artillery, nine army flags, and most of their wounded.”
Sheridan’s chief of staff telegraphed Washington, “We have just sent them whirling through Winchester, and we are after them to-morrow. This army behaved splendidly.” The Federals secured Winchester for the last time, holding the town for the rest of the war.
The Federals sustained 5,018 casualties (697 killed, 3,983 wounded and 338 missing) in what they called the Battle of Opequon. The Confederates lost about 3,921 (276 killed, 1,827 wounded and 1,818 missing or captured) in what they called the Third Battle of Winchester. The Confederate losses equated to about a quarter of Early’s entire army, but he nevertheless asserted that “Sheridan ought to have been cashiered” for allowing the Confederate army to escape relatively intact.
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References
Angle, Paul M., A Pictorial History of the Civil War Years (New York: Doubleday, 1967), p. 181; Catton, Bruce, The American Heritage Picture History of the Civil War (New York: American Heritage Publishing Co., 1960), p. 538; CivilWarDailyGazette.com; Cochran, Michael T., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 648-49; Davis, Jefferson, The Rise and Fall of the Confederate Government: All Volumes (Heraklion Press, Kindle Edition 2013, 1889), Loc 20474-504; Davis, William C., Death in the Trenches: Grant at Petersburg (Alexandria, VA: Time-Life Books, 1983), p. 136; Denney, Robert E., The Civil War Years: A Day-by-Day Chronicle (New York: Gramercy Books, 1992 [1998 edition]), p. 460; 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 11629-49; Fredriksen, John C., Civil War Almanac (New York: Checkmark Books, 2007), p. 497-98; Hoffsommer, Robert D., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 640; Lewis, Thomas A., The Shenandoah in Flames: The Valley Campaign of 1864 (Alexandria, VA: Time-Life Books, 1983), p. 109, 112, 118, 122; Long, E.B. with Long, Barbara, The Civil War Day by Day (New York: Da Capo Press, Inc., 1971), p. 570-72; 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. 776-77; Ward, Geoffrey C., Burns, Ric, Burns, Ken, The Civil War (New York: Alfred A. Knopf, 1990), p. 332-33; Wert, Jeffry D., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 260-61, 328, 677-79, 835