The Battle of Waynesboro

March 1, 1865 – Major General Philip Sheridan’s Federal cavalry advanced to within seven miles of the last substantial Confederate force in Virginia’s Shenandoah Valley. The Federals attacked the next day.

Federal Major General Philip Sheridan | Image Credit:

“Little Phil” Sheridan had left Winchester with 10,000 cavalry troopers under Major General Wesley Merritt in late February. They had orders from Lieutenant General Ulysses S. Grant, the overall Federal commander, to destroy what remained of the Valley to increase pressure on Confederate General Robert E. Lee’s starving army under siege at Petersburg. The Federals marched through Harrisonburg early on the 1st and continued toward Staunton.

Their only opposition was what was left of Lieutenant General Jubal Early’s Army of the Valley near Staunton. This once formidable force now consisted of just two decimated brigades and some artillery. Cavalry was also scattered throughout the region. When “Old Jube” learned that the Federals were heading his way, he called for the cavalry to concentrate. Brigadier General Thomas L. Rosser and 100 troopers rode out to stop the Federals.

Brigadier General George A. Custer’s division led the Federal advance and tried seizing a key bridge over the Middle Fork of the Shenandoah River, also known as the North River. Rosser’s Confederates set the bridge on fire and waited for the Federals in rifle pits on the other side. The Federals outflanked Rosser by fording the river above and below the bridge, thus forcing the Confederates to retreat.

Merritt reported, “This command, under Rosser, was dispersed, captured, or killed. A number of wagons were taken and destroyed by the advance.” The Federals also saved the bridge from destruction, which ensured a quick crossing by the rest of Sheridan’s men. Custer later wrote, “The importance of our success in securing the bridge over North River cannot be over-estimated. Had the enemy succeeded in destroying the bridge it would have compelled a long delay on our part, as there were no fords practicable in the vicinity.”

Rosser and just 30 remaining men joined the main Confederate force at Staunton, where Early ordered a withdrawal to Waynesboro, 15 miles southeast. The Confederates fell back and set up a defense line just west of that town. Their backs were to Rockfish Gap, an important defile in the Blue Ridge. Early wrote:

“My object, in taking this position, was to secure the removal of five pieces of artillery for which there were no horses, and some stores still in Waynesboro, as well as to present a bold front to the enemy, and ascertain the object of his movement, which I could not do very well if I took refuge at once in the mountain. I did not intend making my final stand on this ground, yet I was satisfied that if my men would fight, which I had no reason to doubt, I could hold the enemy in check until night, and then cross the river and take position in Rockfish Gap; for I had done more difficult things than that during the war.”

Brig Gen G.A. Custer | Image Credit:

The Federals entered Staunton later on the 1st and found that the Confederates had stripped it of all supplies before retreating. The Federals camped just outside town that night and then resumed their advance in the morning, with Custer’s division in the lead. Custer reported:

“My orders were to proceed to Waynesborough, ascertain something definite in regard to the position, movements, and strength of the enemy, and, if possible, to destroy the railroad bridge over the South River at that point. The roads were almost impassible, owing to the mud caused by the heavy rains of the past few days. Our march was necessarily slow.”

The Federals easily drove off Confederate pickets at Fisherville before approaching the main enemy line. Custer stated that the Confederates were “posted behind a formidable line of earth-works. His position was well chosen, being upon a range of hills west of the town, from which his artillery could command all approaches, while his infantry could, by their fire, sweep the open space extending along their entire front.”

Custer dismounted his men and determined that Early’s front was too strong to break. “But one point seemed favorable to attack,” Custer wrote. “The enemy’s left flank, instead of resting on South River, was thrown well forward, leaving a short gap between his left and the river. The approach to this point could be made under cover of the woods.”

Custer dispatched three regiments under Colonel Alexander Pennington to assault the Confederate left, which was commanded by Major General Gabriel Wharton. Early saw the movement and later wrote, “I immediately sent a messenger with notice of this fact to General Wharton, who was on that flank, and with orders for him to look out and provide for the enemy’s advance; and another messenger with notice to the guns on the left, and directions for them to fire towards the advancing force, which could not be seen from where they were.”

But Wharton was with Early when the Federals poured out of the woods at 3:30 p.m., and he could not alert his men in time. Early “pointed out to him the disorder in his line, and ordered him to ride immediately to that point and rectify it. Before he got back, the troops gave way on the left, after making very slight resistance, and soon everything was in a state of confusion and the men commenced crossing the river.”

As the Confederate left crumbled, two mounted Federal regiments rode straight through the center of the line, leaping over the fortifications and sending the Confederates fleeing through the mud and snow. The Federals chased them through the streets of Waynesboro until nearly all were killed, wounded, or captured. Early rode to the river and implored his men to turn back and fight, “but they could not be rallied, and the enemy forded the river above and got into our rear.”

Pennington wrote, “The movement was completely successful. The entire line of the enemy was thrown into confusion and obliged to retreat, many throwing away their arms and accouterments to enable them to do so more effectually.” Custer reported, “The rout of the enemy could not have been more complete; no order or organization was preserved. The pursuit was taken up by my entire command, and continued through Rockfish Gap for a distance of twelve miles.”

Early barely escaped capture as he rode off with some of his staff to Jarman’s Gap, out of the Federal pursuers’ reach. He wrote that he “rode aside into the woods, and in that way escaped capture. I went to the top of a hill to reconnoiter, and had the mortification of seeing the greater part of my command being carried off as prisoners, and a force of the enemy moving rapidly towards Rockfish Gap.”

Early and the few Confederates not captured eventually returned to Richmond. Public opinion turned against Early for the many defeats he had sustained leading up to the virtual destruction of his army. General Lee was therefore forced to relieve him of command.

Meanwhile, Custer tallied the spoils of the Federal victory:

“Among some of the substantial fruits of this victory we had possession of about 1,800 prisoners, 14 pieces of artillery, 17 battle-flags, and a train of nearly 200 wagons and ambulances, including General Early’s headquarters’ wagon, containing all his official desks and records. The result of this engagement was of the highest value and importance to us for another reason; it opened a way across the Blue Ridge Mountains through Rockfish Gap, and thereby saved us from several days’ delay and marching.”

The Waynesboro rout permanently ended Confederate opposition in the Shenandoah Valley. Not only did it deprive Lee of a final infantry reserve, but it gave Sheridan free reign to spend most of this month laying waste to the region before rejoining the Federals at Petersburg. Sheridan’s Valley campaign, which had begun last August, was a stunning Federal success from which the Confederates would never recover.



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