The winter of 1864-65 was one of the harshest on record in Virginia’s war-torn Shenandoah Valley. Heavy snows and frigid temperatures conspired to freeze into place two opposing armies that had just spent the previous fall contending for control of the vital Southern breadbasket. In Winchester, at the northern end of the valley, the Union Army of the Shenandoah, commanded by feisty Major General Philip H. Sheridan, rested in comparative comfort, well-supplied by the efficient Federal Quartermaster Corps — notwithstanding the veteran soldiers’ seemingly unbreakable habit of eating up five days’ rations in four days’ time. Meanwhile, 90 miles to the south at Staunton, Lieutenant General Jubal A. Early’s Confederate Army of the Valley shivered and starved in stark contrast to their victorious enemy. Early’s thrice-beaten soldiers huddled in their run-down huts and ragged tents, their morale as low as the arctic temperatures outside. ‘Men’s spirits dull, gloomy and all are evidently hopeless, waiting for we know not what end,’ one private wrote.

The two armies’ contrasting moods mirrored their commanders’ divergent fortunes. ‘Little Phil’ Sheridan, all 5 feet 5 inches of him, stood high in the ranks of public opinion. His three successive victories in the Shenandoah Valley, at Winchester, Fisher’s Hill and — most prominently — Cedar Creek, had effectively ended two years of Union frustrations in the Confederacy’s most important granary. Tough, unsentimental and confident to the point of cockiness, Sheridan had more than justified Lt. Gen. Ulysses S. Grant’s controversial decision the previous summer to give him command of the Army of the Shenandoah. Told by more than one person that the diminutive Sheridan was ‘rather a little fellow,’ the taciturn Grant had responded, ‘You will find him big enough for the purpose before we get through with him.’

Sheridan’s Confederate counterpart, Jubal Early, was not so sanguine. ‘Old Jubilee’ could more than match Sheridan’s rough, salty language and personal bravery, but he could not match the Federals’ overwhelming advantage in sheer numbers. While Sheridan counted nearly 10,000 battle-tested cavalry troopers in his winter camp, Early could scarcely scrounge together one-eighth that number of Rebel soldiers. To make matters worse, the enemy’s destruction of farms and livestock in the valley had depleted the Confederates’ food and forage supplies. To keep his men and horses from withering away completely, Early had been forced to disperse his already dwindling command. He returned two cavalry brigades to General Robert E. Lee’s equally hard-pressed army at Petersburg and sent another brigade to winter in southwestern Virginia, along with an infantry brigade and an artillery battalion. The situation was so dire that artillerymen who accepted responsibility for feeding their horses were allowed to take them home.

Two months earlier, on the morning of October 19, 1864, neither commander could have guessed what their comparative conditions would soon be. That morning, while Sheridan was still sleeping in Winchester after returning from a whirlwind visit to Washington, Early had sent his army crashing into the Union lines outside Middletown at Cedar Creek. The pre-dawn surprise attack, spearheaded by three divisions under Maj. Gen. John B. Gordon’s command, had nearly destroyed Sheridan’s army. A prematurely jubilant Early, consciously echoing Napoleon’s words at the Battle of Austerlitz half a century earlier, had greeted the rising sun with the satisfied exclamation, ‘The sun of Middletown!’

An unaccountable delay in pressing the attack — Gordon accused Early of shrugging off his calls for another charge with the airy reasoning, ‘This is glory enough for one day’ — had allowed Sheridan to ride back to his army in a stirring 10-mile dash known ever afterward as ‘Sheridan’s Ride.’ Once on the field, the Union commander had managed to rearrange his lines and inspire his troops, telling them flatly, ‘We’ll sleep in our own beds tonight, or we’ll sleep in hell.’ A subsequent counterattack, ably supported by Union cavalry, had completely reversed the Confederates’ gains that morning and sent Early and his army stumbling southward in ignominious defeat.

Sheridan’s victory at Cedar Creek, together with Maj. Gen. William T. Sherman’s capture of Atlanta earlier that fall, had gone a long way toward enabling President Abraham Lincoln to win re-election. Lincoln’s victory at the ballot box, in turn, ensured that the North would continue pressing its ‘hard war’ against the South, and nowhere was that concept more harshly carried out than in the Shenandoah Valley. Throughout the fall of 1864, Sheridan’s troopers fanned out across the lower valley, burning barns, poisoning wells, killing livestock and doing all they could to follow their commander’s orders to ‘consume and destroy all forage and subsistence, burn all barns and mills and drive off all stock in the region.’ Valley residents who complained about the wholesale destruction were told, per Sheridan’s instructions, ‘that they have furnished too many meals to guerrillas to expect much sympathy.’

One subordinate who followed Sheridan’s instructions to the letter was Brevet Maj. Gen. George Armstrong Custer. The flamboyant 25-year-old commanded Sheridan’s 3rd Cavalry Division, and that fall he led his troopers on a series of raids and reprisals against the deadly Confederate guerrillas who patrolled the region. Custer directly owed his new rank to Sheridan, who had requested following the Battle of Cedar Creek that Custer and 30-year-old Brig. Gen. Wesley Merritt, whom Sheridan proudly styled his ‘brave boys,’ be promoted. The impetuous Custer, brave to the point of recklessness, was Sheridan’s particular protégé. Perhaps Sheridan saw something of himself in Custer: Both men had struggled mightily to complete their courses at the U.S. Military Academy at West Point. Indeed, Custer was the class ‘goat’ in 1861, finishing dead last academically. More likely, however, the unsentimental Sheridan simply appreciated the young Michigander’s unhesitating obedience to orders and his utter lack of remorse in carrying them out.

Repeatedly that fall, Custer crossed swords with Lt. Col. John Singleton Mosby and his 43rd Virginia Cavalry Battalion. Mosby’s men were legally sworn Confederate soldiers, but their irregular raiding habits caused them to be considered guerrillas, and Custer, for one, was not much troubled by military formalities. In early October, near Dayton, Custer had a Southern bushwhacker summarily shot. Two days later, two more captured Confederates were tried as spies and executed. On October 12, one of Mosby’s horsemen was hanged from a tree alongside a roadway, bearing a placard that read, ‘In retaliation.’ And when a favorite trooper in the 6th Michigan was killed by a sniper shot from one of two adjacent houses, the owners of both houses were dragged outside and shot, without reference to which — if either — was the guilty party. Custer was also blamed erroneously for the execution of six Mosby’s Rangers at Front Royal on September 23. In fact, Merritt had commanded the force that captured the Rangers, but Custer was present when four of the men were shot down in a field behind the Methodist Church — one in front of his screaming mother — and two others were hanged from a nearby walnut tree. The flamboyant Custer was easily the most recognizable Yankee on hand for the killings, and residents of the town mistakenly labeled him the chief perpetrator of the outrage. Mosby, who had not been present for the initial attack, began stockpiling any Custer troopers he managed to capture, and on November 6, at Rectorville, he had 27 Federal prisoners draw numbered slips of paper to determine which seven would be executed in reprisal for the murders at Front Royal and the slaying of a seventh Confederate prisoner on October 13. The unlucky seven were led away (two managed to escape) and executed, with a note left dangling from one of the bodies, reading: ‘These men have been hung in retaliation for an equal number of Colonel Mosby’s men hung by order of General Custer, at Front Royal. Measure for measure.’

The reprisals at Rectorville put an end to the most blatant violations of military code, but they left behind a festering bitterness in Custer and his men. That bitterness was compounded by a surprise attack on Custer’s camp at Lacey Springs in mid-December by members of Brig. Gen. Thomas Rosser’s skeleton cavalry force. With the two opposing armies largely locked into place for the winter, only the cavalry could negotiate the ice-wracked countryside, and Custer and his troopers had set out on a raid toward Staunton. Instead, nine miles above Harrisonburg, Custer’s camp was overrun by Rosser’s hard-charging riders. Little real damage was done, but the blow embarrassed the Union cavalry commander, not least because Rosser had been his best friend at West Point, and Custer was forced to explain to Sheridan — somewhat sheepishly — how he had managed to get himself attacked in his camp in the first place.

Fortunately for Custer, Sheridan was in a forgiving mood, and the incident at Lacey Springs was quickly dismissed, if not forgotten. Custer spent the rest of the winter with his wife, Elizabeth, who had come south to join her husband during his triumphant visit to Washington following the Battle of Cedar Creek. The popular cavalry commander had been selected by Sheridan to lead an honor guard to present a number of captured Confederate battle flags to Secretary of War Edwin Stanton. It was the sort of extravagant ceremony that Custer always excelled at, and even the hard-to-please Stanton was impressed by the young general’s gleaming demeanor. ‘A gallant officer always makes gallant soldiers,’ the secretary told him. Following the ceremony, the Custers made their way back to the Shenandoah Valley — carefully escorted by 150 handpicked men — and set up housekeeping at the home of Robert and Sarah Glass, four miles outside Winchester. The Glasses were Quakers and, in the words of Libbie Custer,’such nice people.’

With winter campaigning at a standstill, the Custers took a 20-day furlough in late January, visiting family and friends in their hometown of Monroe, Mich. A fellow traveler on the train to Michigan jotted down a hasty, hero-worshiping account of the general in his diary. ‘Genl Custar [sic] reminded me of Tennyson’s description of King Arthur,’ wrote Lewis T. Ives. ‘He is tall straight with light complexion, clear blue eyes, golden hair which hangs in curls on his shoulders[,] has a fine nose.’ Kingly or not, Custer took advantage of his furlough to put himself right with God. At a Sunday evening service at the Monroe Presbyterian Church, he experienced a religious conversion, one that left him feeling, Custer said:’somewhat like the pilot of a vessel who has been steering his ship upon familiar and safe waters but has been called upon to make a voyage fraught with danger. Having in safety and with success completed one voyage, he is imbued with confidence and renewed courage, and the second voyage is robbed of half its terror. So it is with me.’

When Custer returned to Winchester in mid-February, he quickly learned from Sheridan what that second voyage would be. For the past four months, since the great Union victory at Cedar Creek, Grant had been urging Sheridan to cut the Virginia Central Railroad at or around Charlottesville and then move eastward toward Richmond and the rear of Robert E. Lee’s lines at Petersburg. For various reasons — inclement weather, Mosby’s guerrillas, the threat of Confederate reinforcements in the valley and just plain stubbornness — Sheridan had resisted. But Grant was impossible to dissuade, and he sent Sheridan a new set of discretionary orders: Sheridan was to destroy the Virginia Central Railroad and the James River canal, capture Lynchburg and then either return to Winchester or link up with Sherman’s army in North Carolina. Sheridan decided to obey Grant’s orders — but only up to a point.

At dawn on February 27, 1865, Sheridan and his cavalry broke camp at Winchester and headed south. Along with two full cavalry divisions and a section of artillery, the blue-clad force included a long train of supply wagons, a pontoon train, 12 ambulances and two medical wagons. Each trooper rode out with five days’ worth of rations for himself, 30 pounds of forage for his horse and 75 rounds of ammunition. Winchester resident Emma Reily observed the departure of the Union invaders. ‘I witnessed one of the grandest spectacles that can ever be imagined as they were leaving,’ she wrote, ‘10,000 cavalry passing our house four abreast, thoroughly equipped in every detail. Their horses, having been in winter quarters so long, had been fed high and curried and rubbed until their coats shone like satin. Each man had a new saddle, bridle and red blanket, and all their accouterments such as swords, belts, etc., shone like gold. It was a grand sight, requiring hours in passing.’

The departure of the Federals was not such a grand event for Jubal Early and his winter-shriveled command in Staunton. Spies in Winchester and soldiers manning the army’s observation and signal station on Massanutten Mountain had already detected signs of the impending Union movement. Nine days earlier, Confederate Private Henry Berkeley confided to his diary: ‘We hear that the Yanks are collecting a very large cavalry force at Winchester and are expected to move up the Valley as soon as the weather permits. I don’t see how it is possible for our little force to make any headway against them. We are only 1,500; they are reported to be 15,000. They will run over us by sheer weight of numbers. Who will be left to tell the tale?’

Berkeley’s estimation of the Federals’ strength was off by one-third, but his apprehension was shared by his army commander. All winter Early had brooded about his three stinging defeats, particularly the lost opportunity at Cedar Creek. Ungenerously, he had blamed that defeat on his own men, complaining to Lee, ‘We had within our grasp a glorious victory, and lost it by the uncontrollable propensity of our men for plunder.’ He failed to mention his own delay at the time of the initial breakthrough, and he flatly declared that the subsequent Confederate retreat had been ‘without sufficient cause,’ a panic created by ‘an insane dread of being flanked and a terror of the enemy’s cavalry.’ That the army had already been outflanked twice before, at Winchester and Fisher’s Hill, and that the Confederate cavalry had been sent reeling at Tom’s Brook were factors Early neglected to mention.

Robert E. Lee, however, could understand clearly enough what had happened, and in the intervening weeks and months he had proceeded to strip Early of much of his command. The skeleton force that still remained in Staunton, Lee advised Early, was simply there ‘to produce the impression that the force was much larger than it really was.’ Gently, Lee advised Early to do the best he could. Faced with a flurry of alarming reports announcing the enemy’s advance up the valley, Early minded Lee’s advice. He directed Rosser to regather his horsemen, who had temporarily disbanded to winter at their homes, and attempt to delay the Union advance at Mount Crawford, where a covered bridge crossed the North River. At the same time, Early telegraphed Maj. Gen. Lunsford Lomax at Millboro, 40 miles west of Staunton, and ordered him to bring his understrength cavalry division back east. Similar orders went to Brig. Gen. John Echols to dispatch his infantry brigade by rail to Lynchburg, which Early assumed was Sheridan’s ultimate target. Finally, Early had all military stores removed from Lynchburg, in case the town fell to the Federals.

The blue column moved up the macadamized Valley Pike on the 27th, stopping to camp for the night at Woodstock. The next morning, with Custer’s 3rd Division in the lead, the march resumed. Despite a steady rain, spirits were high, with Sheridan informing Grant that ‘the cavalry officers say the cavalry was never in such good condition.’ The mood darkened, at least temporarily, when eight troopers drowned while attempting to swim their horses across the rain-swollen North Fork of the Shenandoah River. ‘[M]any others would have been drowned had it not been for the superhuman efforts of a number of officers and men…who rushed into the stream, and at great personal risk brought them to the shore,’ reported the commander of Custer’s 1st Brigade, Colonel Alexander Pennington. The rest of the army waited for the engineers to put out a pre-constructed pontoon bridge.

As early as February 28, Sheridan made it plain to his officers — if not to Grant — that he had no intention of returning to Winchester following the raid. (Whether he intended to head south and join Sherman, as Grant wanted, Sheridan did not say.) At officers’ call that morning, Sheridan gathered his subordinates together and told them ‘that we were on a big march of not less than 350 or 400 miles,’ Sergeant Roger Hannaford of the 2nd Ohio reported — certainly much longer than an advance and return from Winchester to Staunton would require.

Rain continued to fall on the third day of the Union march. Again, Custer’s division took the lead, and at Mount Crawford they ran into a familiar foe, Tom Rosser, who had scraped together a couple hundred cavalrymen and was busy setting fire to the covered wooden bridge across the North River. Custer called for Colonel Henry Capehart, commander of the 3rd Brigade, and ordered him to secure the bridge at all costs. Capehart had just joined Custer’s division after a transfer from the 2nd Division, and he was understandably eager to make a good impression. He quickly had two regiments swim across the river above the bridge, while he personally led the rest of the brigade in a high-throated charge across the burning timbers. Rosser’s men fired a last volley at the oncoming Federals and melted back into the woods, but not quickly enough to prevent the capture of 37 Southerners.

That night the Federals bedded down in an icy shower at Cline’s Mill, seven miles north of Staunton. Sheridan ordered Colonel Peter Stagg’s Michigan brigade to skirt Staunton in the dark and burn the railroad bridge to the east at Christian Creek to prevent the Rebels from evacuating the town. Stagg’s troopers successfully burned the bridge after piling fence rails on top of the span, but they were too late to stop the evacuation. Early and his staff had ridden out of Staunton at 3:45 that afternoon, headed for a fateful rendezvous with Brig. Gen. Gabriel C. Wharton’s ragtag infantry division at Waynesboro, a small village midway between Staunton and Charlottesville on the banks of the South River near Rockfish Gap in the Blue Ridge Mountains.

The next morning Sheridan entered Staunton. The streets were deserted, the warehouses empty, but somehow Early had left word for his old adversary that he intended to fight at Waynesboro — or at least that is what Sheridan reported later. It seems doubtful that Early, leaving in haste with an army eight times the size of his snapping at his heels, would have been so bold as to invite further pursuit. Probably, Early expected Sheridan to continue south to Lynchburg, where ‘Jube’ had already dispatched his largest infantry force. Sheridan later explained that he was reluctant to leave Early’s troops — all 1,200 of them — in his rear, although what possible harm they could have done in their present worn-down state was anyone’s guess. Still, if Early wanted to fight at Waynesboro, Sheridan would be more than happy to accommodate him. Besides, each step Sheridan took to the east carried him that much closer to Grant — and that much farther away from Sherman. All in all, it seemed like a good trade-off.

Sheridan summoned Custer and told him, Custer reported, to ‘ascertain something definite in regard to the position, movements, and strength of the enemy, and, if possible, destroy the railroad bridge over the South River at that point.’ Since Sheridan already knew how many men Early had and where he had gone, the order did not make much sense, but it was all Custer needed to mount up and head east.

In the meantime, Early had reached Waynesboro and set about preparing a makeshift defensive line on a low ridge west of town. General Wharton, a veteran of every major valley fight since the Battle of New Market, was given the unenviable task of holding down a three-quarter-mile-long line of rifle pits with a skeleton force of 1,000 infantry, 100 cavalry and six artillery pieces. The thin-stretched line was a mere 200 yards from the rain-swollen South River, and the sleet-soaked Confederates were uncomfortably aware of the raging watercourse to their rear. To make matters worse, the line did not stretch far enough south to touch the westward bend of the river — a gap of about an eighth of a mile that left the Rebel flank hanging in the air. Captain Jedediah Hotchkiss, Early’s New York–born topographical engineer, charged later that Early had ‘committed an unpardonable error’ in posting his troops in such an exposed position. Early explained, rather lamely, that he had placed the men there in order ‘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.’

Perhaps that was so, but Early was gambling on being able to out-bluff the Federals, and the ever-aggressive Custer was a hard man to bluff. Arriving outside Waynesboro at about 2 p.m. on March 2, Custer sent Colonel William Wells’ 2nd Brigade forward to probe the Confederate line. A brisk rattle of rifle fire convinced Custer that a frontal assault ‘would involve a large loss of life.’ Hastily, he looked for another approach, and soon discovered the dangerous gap between the Rebel left and the river. While Wells kept the enemy occupied in the front, Custer sent Lt. Col. Edward Whitaker, his chief of staff, to relay his orders to Colonel Pennington’s brigade. Custer directed Pennington to dismount three of his regiments and attack the enemy’s flank through a stand of woods that would obscure the troopers’ approach. The three attacking regiments — the 2nd Ohio, 3rd New Jersey and 1st Connecticut — were armed with seven-shot Spencer repeating rifles. The brigade’s fourth regiment, the 2nd New York, was held in reserve.

At a signal from bugler Joseph Fought, the Union forces began the attack. It did not last long. While Lieutenant C.A. Woodruff’s section of horse artillery blasted away at the Rebel breastworks, compelling the defenders to lie flat, Pennington’s men lifted a yell and attacked at a dead run, firing their Spencers as quickly as they could. Meanwhile, Colonel Capehart’s 3rd Brigade stormed into the works from the front. The overwhelmed Confederates broke for the rear in what a disgusted Jedediah Hotchkiss termed ‘one of the most terrible panics and stampedes I have ever seen. There was perfect rout along the road up the mountain.’

Early, who was watching the fight from a hill between the rifle pits and the river, saw at once that ‘everything was lost.’ Cutting through a nearby stand of trees, he and his staff raced for the bridge leading to Rockfish Gap. Early and Wharton made it, but Dr. Hunter McGuire, the army’s gifted medical director, was not so lucky. Attempting to jump his horse over a rail fence, McGuire and his mount went sprawling face first in the mud. When he looked up, a Union cavalryman was pointing a carbine at his head. Thinking quickly, McGuire made the arcane distress sign used by members of the Masonic Order. A Federal officer and fellow Mason immediately rode up and took charge of the shaken physician, telling the other soldier: ‘This man is my prisoner. Let him alone.’

McGuire was one of more than 1,200 Confederates captured at Waynesboro, along with all 11 artillery pieces, 17 battle flags and 150 wagons, including Early’s own headquarters wagon. Union losses were nine men killed or wounded. After a brief pursuit of the handful of Rebel stragglers who made it safely to Rockfish Gap, Custer broke off the attack and reported to Sheridan, who had arrived on the scene.

As Sheridan staffer Captain George B. Sanford remembered: ‘Up came Custer himself with his following, and in the hands of his orderlies, one to each, were the seventeen battle flags streaming in the wind. It was a great spectacle and the sort of thing which Custer thoroughly enjoyed.’

Sheridan, too, enjoyed the scene, praising Custer for the ‘brilliant fight’ and reporting to Washington with pardonable pride that the battle at Waynesboro had ‘closed hostilities in the Shenandoah Valley.’ It had also closed Early’s military career. Never again would Old Jubilee command troops in battle.

While Sheridan went on to complete a brilliant Civil War career and advanced to eventual command of the entire U.S. Army, Early retired to an embittered postwar career as one of the most unreconstructed of all unreconstructed Rebels. The fulcrum of fate that had held both men’s careers in the balance one October morning at Cedar Creek had tipped irreversibly in favor of Phil Sheridan, with a slight assist from his golden-haired protégé, George Armstrong Custer.

This article was written by Roy Morris, Jr. and originally appeared in the March 2001 issue of America’s Civil War. For more great articles be sure to pick up your copy of America’s Civil War.