Part of a series of articles titled Drive the Enemy South.
Previous: Battle of Berryville
Next: Battle of Fisher's Hill
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“Sheridan moved at the time he had fixed upon. He met Early at the crossing of Opequon Creek and won a most decisive victory—one which electrified the country. Early had invited this attack himself by his bad generalship and made the victory easy. He had sent Anderson’s division east of the Blue Ridge…”
Lt. Gen. Ulysses S. Grant
Confederates suffered a costly defeat at the Third Battle of Winchester, September 19, 1864. The largest battle in the Shenandoah Valley saw 54,400 total troops engaged and 8,630 casualties, including over a quarter of the Confederate Army of the Valley. The Confederates' retreat from Winchester to Fisher's Hill was the beginning of the end of their resistance in the Valley.
Shenandoah Valley Battlefields Foundation (SVBF) preserves the battlefield at Third Winchester Battlefield Park and Fort Collier Civil War Center. Visit Third Winchester Battlefield »
Maj. Gen. Philip H. Sheridan and his Army of the Shenandoah were on a roll, literally. The army’s wagon trains, along with horses, cannons, and over 35,000 soldiers were lumbering west toward Winchester, Virginia, on the Berryville Turnpike, the primary Federal avenue of approach. Their intent: destroy the 15,000-man Confederate Army of the Valley under Lt. Gen. Jubal Early, and finally rid the Valley of all secessionist resistance, civilians included.
Other than several cavalry probes and clashes, the tactical situation remained static for the next two weeks as the armies stayed on their own side of Opequon Creek, Confederates to the west, Federals to the east. While Sheridan sought an opening for an attack, United States Army commanding General Ulysses S. Grant decided that visiting Sheridan might prod him into battle.
Meanwhile, Sheridan received intelligence on September 16th that an entire Confederate division of over 3,000 soldiers under Generals R. H. Anderson and Joseph Kershaw had left the Valley. The information was provided by a Winchester Unionist named Rebecca Wright and relayed by a slave named Tom Laws. The shrewd Laws carried Wright’s handwritten note, wrapped in foil and in his mouth, back to Sheridan.
Arriving around 2:00 p.m., Crook sent Col. Isaac Duval’s division across Red Bud Run to turn left, advance west about one mile, ford the stream heading south, and crash into Gordon’s left flank. This was the sector where Breathed’s horse artillery guns had caused so much damage earlier, but now they were gone.
The brigade under Col. Rutherford B. Hayes found the stream very difficult to cross, “twenty or thirty yards wide, and nearly waist deep, with soft brown mud at the bottom,” wrote one Federal veteran. Resistance was fierce as Gordon’s troops and Col. George Patton’s men from Wharton’s division defended the Confederate left flank.
Seeing Duval’s flanking march in trouble, Sheridan sent Col. Joseph Thoburn’s 8th Corps division along Red Bud Run’s south side to hit Gordon’s division near the Hackwood Farm. This strike opened things up for Duval who’s soldiers now crossed the stream and attacked Gordon and Patton.
With the powerful Federal cavalry and their seven-shot repeating Spencer carbines bearing down from the north, Gen. Early had pulled Breckinridge with Wharton’s division south to form a defensive perimeter around Winchester. Now Patton, the grandfather of the WWII hero George S. Patton III, was caught in desperate combat against both Duval’s infantry and Brig. Gen. Thomas Devin’s cavalry brigade.
As the Confederate left flank started to collapse, Patton was mortally wounded by shrapnel and died several days later. The Federal cavalry divisions under Brig. Generals Wesley Merritt and William Averell thundered south toward Winchester and its protective forts, but Breckinridge and Wharton pulled together a patchwork defensive line that bloodied and temporarily stalled the aggressive Federal horsemen.
About two miles south, pressure from the Federal 6th Corps was finally driving the remnants of Ramseur’s and Rodes’s beaten-up divisions west into Winchester. The battle in this sector had become a bloody stalemate, but a counterattack by Brig. Gen. Emory Upton’s brigade spurred on the entire 6th Corps. Sheridan rode up in the afternoon and yelled to some of the soldiers, “give them hell, my men, the only way to do it is kill every son of a b____.”
By 4:30 p.m., the 6th Corps, firing their M1861 Springfield rifle muskets and building momentum, drove the Confederates away. Frustrated Confederate brigade commander Brig. Gen. Bryan Grimes yelled at his retreating men, “I will blow the brains out of the first man who leaves the ranks.” Despite the threats, the outnumbered Confederates gave ground.
The entire Confederate line grudgingly broke apart. Combined arms pressure from Thoburn’s infantry, the relentless Federal cavalry, and horse artillery batteries punished Breckinridge’s and Wharton’s rag-tag defense.
Cavalry brigades under Brig. Generals Thomas Devin and George A. Custer captured hundreds of fleeing Confederates. Col. Charles R. Lowell’s cavalry brigade overran Fort Collier, an earthwork redoubt on Winchester’s north end. The fort’s defenders under the already mortally wounded Captain George Chapman were no match for Lowell’s surging riders who scattered the remaining Confederates and captured two cannons.
Less than a mile west, the cavalry brigades under Colonels James Schoonmaker and William Powell bore down on the earthen structures of Star Fort and Fort Jackson. Schoonmaker’s troops chased Confederate defenders out of both forts.
Despite pockets of enemy resistance, the Federal cavalrymen were enjoying their bloody jobs. Riding, slashing, and killing with their Colt and Remington six-shooters, they got lots of practice as Sheridan’s shock troops. They kept charging toward Smithfield Redoubt, an L-shaped earthwork one-half mile south of Fort Collier where Confederate officers like Gordon, Breckinridge, and Cullen Battle tried to rally a last-ditch defense around the remaining guns of their artillery battalion.
The combat near the redoubt was ferocious as the Federal infantry of the 6th and 8th Corps closed in from the east. But the Federal cavalry was not done. Under Gen. Wesley Merritt’s command, the brigades of Custer, Devin, Lowell, and Powell charged in from the north, thundered over the earthworks, and scattered most of the Confederate defenders, “sabering right and left, capturing prisoners more rapidly than they could be disposed of,” wrote one Federal rider.
Beaten, fleeing Confederates streamed through Winchester. One soldier wrote, “it was the most disorderly retreat I ever saw…the road was filled with fugitives from all commands.” A North Carolinian noted, “I never ran so fast in all my life…” Gen. Early and his officers simply could not stop the retreat south toward Newtown.
After the battle Early wrote, “we deserved the victory, and would have had it, but for the enemy’s immense superiority in cavalry…” Fortunately for the Confederates, Federal pursuit attempts were cautious and disorganized; Early’s bloodied army slipped away to fight again three days later, September 22nd, 1864.
In terms of troops engaged and casualties, Third Winchester was the largest battle in the Shenandoah Valley. Of his approximately 15,000 soldiers, Early lost nearly 4,000 killed, wounded, and missing or captured (approximately 27%), but somehow managed to lose only five cannons. Sheridan lost slightly over 5,000 troops (approximately 13%).
While Early’s army was severely crippled by the casualties, Sheridan could replace his own losses. The Army of the Shenandoah was building confidence and momentum. It was again on a roll, this time following Early’s army south to the “Confederate Gibraltar,” Fisher’s Hill.
Part of a series of articles titled Drive the Enemy South.
Previous: Battle of Berryville
Next: Battle of Fisher's Hill
Last updated: February 1, 2023