Waynesboro was a Civil War engagement fought in Virginia, 1865. It was a Union victory.
On February 27, Maj. Gen. Philip Sheridan with two cavalry divisions rode from Winchester up the Shenandoah Valley to Staunton. Turning east, the Federals encountered the last remnant of Lt. Gen. Jubal Early's Valley army at Waynesboro on March 2. After a brief stand-off, a Federal attack rolled up Early's right flank and scattered his small force. More than 1,500 Confederates surrendered. Early and a few of his staff evaded capture. Sheridan crossed the Blue Ridge to Charlottesville and then raided south, destroying the James River Canal locks near Goochland Court House. He joined forces with the Army of the Potomac near Petersburg on March 26 for the opening of the Appomattox Campaign.
At Waynesboro, located in Augusta County, Virginia, opposing forces clashed on March 2, 1865, in an engagement that would prove decisive during the American Civil War. Brig. Gen. George Armstrong Custer emerged with total success that day, while Confederate Lt. Gen. Jubal Early saw his command wiped out in what turned out to be his last fight of the war.
Philip Sheridan, a Major General, set out from Winchester on February 27, 1865, leading two cavalry divisions up the Shenandoah Valley in the direction of Staunton. His superiors had instructed him to bring his horsemen south so they could unite with Major General William T. Sherman's forces in the Carolinas campaign. The following day, February 28, after fording the North Fork of the Shenandoah River, the division commanded by Brigadier General George Armstrong Custer ran into roughly 300 Confederate horsemen posted under Brigadier General Thomas Rosser near Mount Crawford, where they were guarding the Middle River. In an attempt to slow the Federal advance, Rosser set fire to a lengthy covered bridge. Custer responded by sending two regiments swimming across the river to hit Rosser's flank while his remaining regiments charged directly at the bridge. This combined assault pushed Rosser's small force back, allowed the flames to be put out, and cleared the way for Custer to reach Staunton, where the rest of Sheridan's command caught up with him a day later. Rather than continuing on toward Sherman, Sheridan chose to swing east, intent on removing the threat that Early's modest army posed to his rear.
On March 2, Custer's troopers moved out toward Waynesboro, where Early's men were positioned, carrying instructions to advance on the town, gather solid intelligence about the enemy's location, movements, and numbers, and, if the opportunity arose, to wreck the railroad bridge spanning the South River there. Days of relentless rain mixed with sleet had reduced the roads to thick mud, slowing the column's progress considerably. Near Fishersville, only six miles short of Waynesboro, Custer's men pushed aside a line of Confederate vedettes before pressing forward. When they reached the outskirts of Waynesboro, they discovered that Early had entrenched his army behind what was described as a formidable line of earthworks.
Waynesboro's western approach featured a low ridge where Early arranged his forces, with earthworks running along the whole line. The far right held three cannon from Kirkpatrick's Amherst Artillery, while one infantry brigade occupied the right-center. A small body of cavalry along with a second infantry force, likely Harman's militia, held the middle ground. Just to their left stood Milledge's Georgia Regular Battery alongside Snead's Fluvanna Artillery, and Early's remaining infantry brigade anchored the far left. That left flank, though, sat open and unprotected, since Early wrongly assumed thick woodland would block any Federal advance from that direction. Worse still, the layout of his lines left only two paths of retreat across the swollen South River, a rail crossing and a modest footbridge. Early would later insist he intended to pull back once night fell and cover his withdrawal, adding that supplies and guns still needed transport to safer ground.
Around two in the afternoon, as Custer's troopers reached the edge of town, the two sides opened up with artillery fire. Custer pushed Colonel William Wells and his Second Brigade forward to test the Confederate line, quickly finding it well fortified. Soon afterward, though, Custer discovered a critical opening between the enemy's left flank and the riverbank. Seeing a chance to avoid the heavy losses a frontal assault would bring, he directed Colonel Alexander Cummings McWhorter Pennington Jr. to lead three
For twelve miles Custer's troopers chased the broken Confederate ranks until nightfall finally halted the chase. Federal officers afterward asserted they had taken somewhere between 1,000 and 1,800 prisoners, along with 11 to 14 pieces of artillery, 150 to 200 wagons, and 16 flags, one of which was a Union banner recovered from earlier loss. Early pushed back hard against these numbers, yet other evidence, notably the fifteen Medal of Honor awards given specifically for seizing flags at Waynesboro, points toward the Federal tallies being nearly accurate. Whatever the precise count, every account agrees that Early's entire artillery train, his wagons, and his ambulances were lost, and that his infantry emerged too broken to function as a real fighting force for the remainder of the conflict. Custer reported his own casualties at only nine men killed or wounded.
From there Sheridan moved across the Blue Ridge toward Charlottesville, then swept south, wrecking the locks of the James River Canal close to Goochland Court House. On March 26 he linked up with the Army of the Potomac near Petersburg, marking the start of the Appomattox Campaign. Early would never again hold a field command before the war ended.
Captain Christopher C. Bruton, serving with the 22nd New York Cavalry, was later awarded the Medal of Honor for seizing Early's own headquarters flag during the fighting.
Second Lieutenant Andrew Kuder, of Company G in the 8th New York Cavalry, likewise earned the Medal of Honor for remarkable bravery and for capturing a flag.
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