Battles in the East

“Disasters Commenced” – Battle of Third Winchester, September 19th, 1864

1864 was a productive and effective year in the Civil War. With Ulysses S. Grant at the helm, the Union armies in all theaters of the war had made progress in tightening the noose around the Confederacy. The branches of Grant’s ultimate plan included his Overland Campaign against Robert E. Lee’s Army of Northern Virginia, William T. Sherman’s advancement through Georgia and the capture of Atlanta, navy Admiral David Farragut’s siege of the port of Mobile, and the rampage of General Philip Sheridan through the Shenandoah Valley. The last of these branches aided Grant’s efforts further east in Virginia, clearing a backdoor to Richmond and depriving the Confederate army of its “Bread Basket.”

Few regions had been so hotly contested as the Shenandoah Valley. Cities like Winchester had been taken, given up, and retaken again by both sides dozens of times throughout the war (with Winchester changing hands over 70 times), and once again, both armies were at their doorstep. After his success against Confederate cavalry commander J.E.B. Stuart, Sheridan was given command of the Army of the Shenandoah as well as the newly formed Army of West Virginia, a total force of about 40,000 Federal troops, and given the task of sweeping out all Confederate opposition in the Valley. This meant going up against Confederate Jubal Early, Lee’s “Bad Old Man,” who had a propensity for cursing and a short fuse. Early had already given the Union a scare with his short-lived assault on the defenses around Washington D.C. in the summer of 1864. Early’s corps was made up of 13,000 troops, only 9,000 of which were infantry and artillery. Sheridan’s advantage lay in his three units of cavalry, which had been utilized as a striking force as opposed to a means of reconnaissance or guarding supplies – as General George Gordon Meade had argued prior to the campaign.

The opening of the Shenandoah Valley Campaign began in August and September of 1864, about the same time that Sherman had taken Atlanta, Grant had Lee pinned down around Petersburg, and Mobile fell to Farragut further south. Sheridan and Early took turns advancing up and down the Valley through the month of August, both gauging the other. Sheridan eventually took up a defensive position at Berryville, strengthening earthworks there. Sheridan’s hesitance lay in the news that Lee and Early were aware of Sheridan’s intentions and sent Richard Anderson’s corps to reinforce Early’s corps. However, during Sheridan’s feign down the Valley (northward), Anderson’s corps was called back to Petersburg. Sheridan devised a new plan to go on the offensive, altered only slightly from the plan that Grant had previously approved. Word of Early’s choice to place two of his divisions just north of Winchester gave Sheridan the confidence to obliterate the strung-out Confederate army. Official orders were sent out on September 18th for the Army of the Shenandoah to move out the following morning.

Sheridan would send James Wilson’s cavalry through the Berryville Canyon – a steep sided, narrow funnel of a road leading into Winchester – and attack Confederate General Stephen Ramseur’s division, the only enemy force that stood between the entire Federal cavalry and the town. On paper, the plan was to assault Ramseur’s division and then swallow up the Confederate reinforcements piecemeal with the Federal army that would follow up Wilson’s cavalry through the Canyon. Ramseur’s men gave way to the Federal cavalry, fighting as they retreated on the morning of September 19th. It was just enough to delay Sheridan’s plans, but were just as much of a nuisance as the traffic jam of infantry and artillery that tried to make their way through the Berryville Canyon. Speed and coordination had been the key to executing his plan and both had failed him that morning.

This gave Early time to call up two more divisions under Major General Robert Rodes and John Gordon, who deployed between 9 and 10am and contested with the first corps out of the canyon, Horatio Wright’s VI Corps, in the fields just south of the Berryville Pike. Astride the Pike, the reinforcing Confederate divisions fell onto Ramseur’s left, with Gordon’s left flank resting on Red Bud Run. While Union cavalry diverted to the infantry’s left flank, Confederate cavalry did the same and guarded both flanks of the three divisions. The battle began at 11:40am with the advancement of George Getty’s division against Ramseur.

A gap quickly formed between Getty’s right, comprised of the veteran Vermont Brigade, and the left of Rickett’s division. This was due to the Vermonters taking cover in a ravine just south of the road as they came under heavy Confederate fire, while the other divisions continued on straight toward the enemy’s position.

During a counter attack, Robert Rodes’ division lost their commander to either a bullet or artillery shrapnel. His death “shook the whole corps” and “caused such deep regret.” Driven by the loss, the division charged straight for the gap, widening it to the horror of Sheridan watching from Eversole’s Knoll south of the canyon. David Russell’s division in reserves were called up to plug the gap. The score was made even as Russell was struck by an exploding shrapnel and died instantly on the field, but not before sending on Brigadier General Emory Upton’s brigade to his right. Upton, famous for his approach at Spotsylvania that May previous, charged forward, faced his brigade to the left toward the Confederate line, and unleashed a thunderous volley. This effectively drove the Confederate line back.

To the right of Wright’s corps formed the XIX Corps of William Emory. His line stretched through a thicket known as the First Woods, with Brigadier General William Dwight connecting to Rickett’s division and Brigadier General Cuvier Grover’s to Dwight’s right. When the battle opened, Emory’s corps pushed through the thicket into an open field, facing a Second Woods on the other side and driving Confederate skirmishers in that direction. Gordon’s line wavered and broke, only salvaged by their artillery that stalled the Union advance. Gordon rallied his men and reversed the rout into an aggressive offensive counterassault. Dwight’s division staunched the Union rout with a stiff volley, pushing the Confederates back across the field before they could reach the First Woods. This seesaw action ended with both sides content to shoot at one another from their respective woods.

Needless to say, Sheridan’s grand plan to chew up the Confederates piecemeal had not gone as he intended. His VI and XIX Corps were now at a standstill against Early’s three divisions. But Sheridan still had a trick up his sleeve, the Army of West Virginia he had been holding in reserves. Despite their name, these troops hailed from Ohio, Massachusetts, and Pennsylvania, and had been nicknamed the “Mountain Creepers” for their reputation in the mountains of western Virginia and Tennessee. Sheridan ordered their commander, Major General George Crook, up through the Berryville Canyon to reinforce his struggling line, and they fell in on Emory’s right in the First Woods. At the same time, Early called forward John Breckinridge’s division under the command of Brigadier General Gabriel Wharton to also bolster his line.

First Woods, Winchester (author photo, 2021)

At 3pm, the attack was launched with Crook piloting the assault across Red Bud Run, successfully driving the Confederates out of the Second Woods, but no further. The Confederates kept up a galling fire and refused to break. Though outnumbered, the Confederates managed to bring the Federal advance to a crawl before sheer numbers overwhelmed. Sheridan, however, had regained the initiative and ordered a general advance all along the line and pulled out one more ace, his cavalry. His two divisions of cavalry crossed the Opequon River just north of Winchester (upon the Union’s right flank) to engage with the Confederate cavalry guarding their left flank. The Union cavalry beat back the Rebel cavalry and made their way south toward Winchester.

With bugles blaring, the mounted Federals stormed toward Fort Collier, a Rebel fortification constructed in 1861, and crumbled the left Confederate flank. The Confederate Army of the Valley broke under the pressure of cavalry on their left and infantry in their front. The town was evacuated by the Confederates for the last time, and no Rebel force would occupy Winchester for the rest of the war. Sheridan ordered a pursuing march for the following day, unwilling to let Early take a breather after his defeat.

Union: 5020
Confederate: 3610

Touring Third Winchester

Out of the three battles that took place at Winchester, the third during the Shenandoah Campaign of 1864 is the most preserved. That is, there is actually land set aside and interpreted for the public. However, there are some extra locations that can be safely visited.

Eversole’s Knoll – 143 Greenwood Road, Winchester, VA 22602
This is the hill where Sheridan watched the battle unfold and where his headquarters were set up. This hill was once part of J.A. Eversole’s farm and extends to the furthest western reaches of the Berryville Canyon. Looking toward the Berryville Pike, you’d be looking over the contested area of September 19th.

(On your way to the First Woods via GPS, you made travel through the Berryville Canyon, the avenue of the Union army’s approach. Notice how steep the sides are and imagine trying to funnel any army down this road.)

Red Bud Run, Third Winchester Battlefield Trail Map

First Woods
541 Redbud Road, Winchester, VA 22603
Perhaps the largest section of preserved battlefield in Winchester, the trails take you on Crook’s line of advance into Early’s left flank.

Fort Collier
922 Martinsburg Pike, Winchester, VA 22601
This is the site of the Confederate left-wing collapse on September 19th. The earthworks were originally built in 1861. The Fort Collier Civil War Center, Inc. is a non-profit organization dedicated to the preservation of the earthworks at Fort Collier Civil War site in Winchester, Virginia. FCCWC purchased the 10-acre Fort Collier tract on April 1, 2002. Purchase was made possible through private donations totaling approximately $295,000 and approximately $176,000 in grants. For more information about Fort Collier, visit their website: httsp://

Fort Collier, Winchester (author photo, 2021)

There are MANY more Civil War related sites in Winchester, which will be covered in other blog postings.

Recommended Reading:

“Bloody Autumn: The Shenandoah Valley Campaign of 1864” by Daniel Davis and Phillip Greenwalt

“The Shenandoah Valley Campaign of 1864” Edited by Garry Gallagher (collection of essays on the campaign)

2 thoughts on ““Disasters Commenced” – Battle of Third Winchester, September 19th, 1864”

  1. Great article! The Shenandoah Valley campaign of 1864 isn’t exactly one of my strong suits, so I learned something here. I’ve passed through Winchester several times in the past but have never visited the battlefield. I see myself stopping by to check it out in the near future though. Winchester and New Market sounds like it could make for a nice weekend of touring…


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