Following his defeat at Winchester, Jubal Early moved his army south up the valley to Fisher’s Hill. From a military topography point of view, his new position was a dominating one. Early placed his army on high ground that extended nearly across the entire valley floor. Wharton's division was entrenched on the Confederate right flank along a high bluff and extended to the left to cover the Valley Pike. On his left, Gordon's division was placed from the Valley Pike across Manassas Gap Railroad to near the Middle Road above the hamlet of Fisher's Hill. Ramseur’s old division, now led by John Pegram, was positioned to Gordon's left, and Rode's division, now under the command of Stephen Ramseur, extended the line west to a high hill south of Tumbling Run South Fork. While Lomax’s cavalry extended the main line northwest to and beyond the Back Road, it was little more than a skirmish line, which essentially left Ramseur’s flank “in the air.”
However, at first, Early was not overly concerned about his left flank because Lomax's position was at the base of the steep, rough terrain of Little North Mountain. As a result, he probably felt confident that no Union force could realistically threaten his left. Plus, he had a commanding view from atop the hill and his artillery covered every possible approach. One Southern officer referred to the Fisher’s Hill defenses as “our Gibraltar.” However, Early began to worry his position was not so impregnable. He realized that, while his position was impressive, he no longer had enough men to man the line. With his casualties at Winchester, his effective strength was reduced to about 10,000 men. As he rode his line, he realized how thin it truly was. By the afternoon of September 22, “Old Jube” had decided to abandon Fisher’s Hill, issuing an order for a nighttime retreat up the valley. However, his decision to fall back came too late.
Sheridan, far from being the passive, meek opponent Early had originally thought him to be, was aggressively pushing forward. At midday on September 21, he advanced his army south, massing most of VI Corps in a horseshoe opposite Early’s right-center, north of Flint Hill. For its part, XIX Corps had been so badly weakened by the fight at Winchester that Sheridan elected to place it on his left and had the corps entrench, hoping not to have to ask too much of it. Crook's Army of West Virginia was held in reserve and out of sight from the Confederate line. Averell's cavalry division, meanwhile, was assigned to cover Back Road, which ran along the base of Little North Mountain. The rest of Sheridan's cavalry was sent to advance up the Luray Valley to probe Early’s right.
Almost as soon as Sheridan’s men were in position, skirmishing began in earnest. Surveying what lay ahead, Sheridan discovered that the two rises called Flint Hill blocked his view of Early’s position. The hill was defended by a Confederate skirmish line entrenched in what was termed “bull pens,” U-shaped barricades made up of fence rails and filled in with earth. Not to be denied a decent view of the enemy, Sheridan ordered units from VI Corps to take the hill. After two attacks by three regiments failed, he sent an entire brigade of five regiments in to finish the job. Now, Sheridan not only had a clear view, but a commanding position for his infantry and artillery.
Sheridan then set in motion a plan designed to attack Early where he was the most vulnerable and from where he least expected it: on the Confederate left from Little North Mountain. For this difficult task, Sheridan needed men who were prepared to march through rough mountainous terrain. Crook’s West Virginians were ideally suited to the task, so, after sunrise on September 22, he ordered them to move forward up the mountainside. The entire force of 5,000 men quietly marched towards Early’s left, following deep ravines and staying in the forest, safely out of sight of Confederate observers. Although two of those observers would see evidence of Crook’s movement and report it to Ramseur, the usually vigilant young general seems to have taken no notice or discounted the reports entirely.
As Crook’s men climbed Little North Mountain, Ricketts division of VI Corps advanced to take control of the high ground overlooking the North Fork of Tumbling Run, while Averell's cavalry division moved south down Back Road until they linked with Ricketts’ right flank. The VI Corps skirmish line was now within range of Early’s defenses and began steadily popping away at the Confederates. Ricketts, meanwhile, formed his division behind the crest of the hills and awaited Crook's attack.
Crook’s “Mountain Creepers,” as they soon would call themselves, moved relentlessly but silently forward along Little North Mountain. Crook ordered the color bearers in his command to trail their flags so they could not be seen. He also directed his troops to discard their knapsacks and arrange their canteens and bayonet scabbards such that they would not rattle and reveal the army’s position. Around 2:00 p.m., Crook began a flanking movement along the shoulder of the mountain, forming his men into two parallel columns and marching south until more than half of the command was beyond the Confederate left flank. Encountering only sporadic fire from a few of Lomax’s cavalry pickets, Crook ordered his troops forward.
Map image used with permission by the Civil War Preservation Trust
Around 4:00 p.m., all was in readiness and Crook ordered his columns to face left and to charge. The West Virginia and Ohio boys moved at the double-quick down the side of the mountain, shouting at the tops of their lungs. Lomax’s cavalry shook off their momentary astonishment, took to their horses, and scattered in wild confusion. Charging down the hill pell-mell, Crook's troops quickly lost all semblance of order, becoming a massive wave of men pouring toward Ramseur’s infantry on what is now called “Ramseur’s Hill.” Jubal Early had never been so utterly surprised.
Soon, the blue wave split and one part funneled to the right along an old road towards the rear of the Confederate positions. One brigade of North Carolinians tried desperately to hold out against Crook's assault but, suddenly, they heard the sound of Rickett’s VI Corps division, which Sheridan had unleashed against Ramseur’s front, charging to their right and rear. From the sounds of battle, the Tar Heels knew that they were flanked. The North Carolinians fled, and Ramsuer’s entire division was now flanked by Crook’s assault. Sheridan quickly seized the moment and ordered an advance by the entire Army of the Shenandoah. Literally within minutes, Early’s whole defensive line across the valley collapsed and his army fled southward, abandoning equipment and artillery pieces.
With his army in shambles, Early tried to collect his men at the base of Round Hill on the Valley Pike. Gordon, Ramseur, and Pegram established a rear guard of artillery and infantry at Prospect Hill, holding off what was a badly disorganized Union pursuit. Meanwhile, hundreds of Confederates either fled into the mountains or simply surrendered, telling their Federal captors that they were tired of “poor rations and sound lickings.” In one instance, a captured officer from Virginia, who was being escorted to the rear, encountered his son, a Union soldier in the 13th West Virginia. The two men silently shook hands, tearfully embraced, and then the elder soldier continued his journey down the road to captivity. Nearby, a group of Union officers came upon one ragged Confederate prisoner, crouching next to a fire, shivering, and singing a song. The one line they could clearly hear said, “Old Jube Early’s about played out.” And, on this cool September night, that is exactly how it seemed. But “Old Jube” was not done just yet and there was one more act to play in the Shenandoah.