On arriving at the front, where the work of reorganization was already well advanced, Sheridan inspired his men with new courage by his appearance and words. For two hours he rode back and forth in front of the line, encouraging the troops; and when the order was given, "The entire line will advance, etc.," the infantry went steadily forward upon the enemy. Early's front was soon carried, while his left was partly turned back; and after much desperate fighting, his astonished troops turned and fled in utter confusion over the field.
"As they streamed down into the Middletown meadow," says Headley, "Sheridan saw that the time for the cavalry had come, and ordered a charge. The bugles pealed forth their stirring notes, and the dashing squadrons of Custer and Merritt came down like a clattering tempest on the right and left, doubling up the rebel flanks, and cleaving a terrible path through the broken ranks. Back to, and through our camp, which they had swept like a whirlwind in the morning, the panic-stricken rebels went, pellmell, leaving all the artillery they had captured, and much of their own, and strewing the way with muskets, clothing, knapsacks, and everything that could impede their flight. The infantry were too tired to continue the pursuit, but the cavalry kept it up, driving them through Strasburg to Fisher's Hill, and beyond, to Woodstock, sixteen miles distant."
After the battle of Cedar Creek and during the winter of 1864—5, Sheridan's army, including Custer's division, remained inactive, occupying cantonments around Winchester.
On the 27th of Feb., Sheridan started out on his last great raid, taking with him Gen. Merritt as chief of cavalry, the First and Third divisions of cavalry under Generals Devin and Custer, artillery, wagons, and pack-mules. The raiding column, including artillerymen and teamsters, numbered 10,000 men.
Moving rapidly up the Shenandoah Valley over the turnpike road, they passed many villages without halting or opposition, and on the 29th, approached Mount Crawford, where Rosser with 400 men disputed the passage over a stream and attempted to burn the bridge; but Col. Capehart of Custer's command, which was in advance, by a bold dash drove Rosser away and saved the bridge.
Custer now pushed on to Waynesboro' and finding Early intrenched there, immediately attacked him. The result, as told by Sheridan, was as follows:—
"Gen. Custer found Gen. Early in a well chosen position, with two brigades of infantry, and some cavalry under Rosser, the infantry occupying breastworks. Custer, without waiting for the enemy to get up courage over the delay of a careful reconnaissance, made his dispositions for attack at once. Sending three regiments around the left flank of the enemy, Custer with the other two brigades, partly mounted and partly dismounted, at a given signal attacked and impetuously carried the enemy's works; while the Eight New York and the First Connecticut cavalry, who were formed in columns of fours, charged over the breastworks, and continued the charge through the streets of Waynesboro', sabring a few men as they went along, and did not stop until they had crossed the South Fork of the Shenandoah, (which was immediately in Early's rear) where they formed as foragers, and with drawn sabres held the east bank of the stream. The enemy threw down their arms and surrendered, with cheers at the suddenness with which they had been captured."
Sixteen hundred prisoners, 11 pieces of artillery, 200 loaded wagons, and 17 battle-flags were captured single-handed by Custer at Waynesboro', while his own loss was less than a dozen men. Vast amounts of public property were subsequently destroyed. The prisoners were sent to Winchester under guard.
Pushing on across the Blue Ridge in a heavy rain during the night after Early's defeat, Custer, still in the van, approached Charlottesville the next afternoon, and was met by the authorities, who surrendered to him the keys of the public buildings as a token of submission. The balance of the column soon came up, and two days were spent in destroying bridges, mills, and the railroad leading to Lynchburg.
Sheridan now divided his command, and sent Merritt and Devin to destroy the canal from Scottsville to New Market, while he and Custer tore up the railroads as far west as Amherst C.H. The columns united again at New Market on the James River; and as the enemy had burned the bridges so they could not cross to the south side, they moved eastward behind Lee's army, destroying bridges, canals, railroads and supplies, thus inflicting a more serious blow to the confederate cause than any victories by land or sea gained during the last campaign. Then they swept around by the Pamunkey River and White House, and joined Grant's besieging army in front of Petersburg, March 27th. They encamped on the extreme left of the lines, close to their old comrades of the Second Division of cavalry, (now under Gen. Crook) who here again came under Sheridan's command.