It had been a long and grueling War in the Shenandoah Valley with some towns changing hands some seventy times between Union and Confederate forces. On March 2, 1865 it came to an end. Jubal Early’s force, stripped over the winter to shore up Lee’s thin ranks holding the lines at Petersburg, was now reduced to 1500 men. Sheridan was moving South, initially under orders to move into North Carolina and link up with Sherman advancing into North Carolina. Not wanting to leave Early in his rear, Sheridan sent twenty-five year old Brigadier General George Armstrong with a division of cavalry, 2,500 men, to find Early.
Custer had graduated dead last in his class at West Point in 1861, making him the class goat. The “goat” had a spectacularly successful War, rising in rank from Second Lieutenant to Major General of Volunteers. (He had been promoted from Captain to Brigadier General of Volunteers, passing over the intervening ranks, in 1863.) Daring and combative, Custer had helped transform Union cavalry from lackluster to an able strike force.
Early posted his small force on a ridge due west of Waynesboro, Virginia. Arriving at 2:00 PM on March 2, Custer quickly saw that Early had fortified his position and that head on attacks would probably not work, but that Early’s left could be turned. (Early had thought that a thick wood adequately protected this flank.) Sending one brigade to turn the Confederate left while he attacked frontally with two brigades worked to perfection. Virtually the entire Confederate force was taken prisoner with Early and fifteen to twenty Confederates escaping. Here is Sheridan’s account of the battle from his Memoirs:
General Early was true to the promise made his friends in Staunton, for when Custer neared Waynesboro’ he found, occupying a line of breastworks on a ridge west of the town, two brigades of infantry, with eleven pieces of artillery and Rosser’s cavalry. Custer, when developing the position of the Confederates, discovered that their left was somewhat exposed instead of resting on South River; he therefore made his dispositions for attack, sending around that flank the dismounted regiments from Pennington’s brigade, while he himself, with two brigades, partly mounted and partly dismounted, assaulted along the whole line of breastworks. Pennington’s flanking movement stampeded the enemy in short order, thus enabling Custer to carry the front with little resistance, and as he did so the Eighth New York and First Connecticut, in a charge in column, broke through the opening made by Custer, and continued on through the town of Waynesboro’, never stopping till they crossed South River. There, finding themselves immediately in the enemy’s rear, they promptly formed as foragers and held the east bank of the stream till all the Confederates surrendered except Rosser, who succeeded in making his way back to the valley, and Generals Early, Wharton, Long, and Lilley, who, with fifteen or twenty men, escaped across the Blue Ridge. I followed up the victory immediately by despatching Capehart through Rock-fish Gap, with orders to encamp on the east side of the Blue Ridge. By reason of this move all the enemy’s stores and transportation fell into our hands, while we captured on the field seventeen battle flags, sixteen hundred officers and men, and eleven pieces of artillery. This decisive victory closed hostilities in the Shenandoah Valley. The prisoners and artillery were sent back to Winchester next morning, under a guard of 1,500 men, commanded by Colonel J. H. Thompson, of the First New Hampshire.