Confederate guerilla leader John Singleton Mosby and his intrepid Rangers are known for their incredibly daring feats, but they weren’t always successful. One chilly night in the winter of 1864, the Union calvary met the Confederates’ surprise raid with a bloody defeat.

On December 30th about eighty members of Cole’s Cavalry (or the 1st Regiment Potomac Home Brigade, named after its commander twenty-nine-year-old Major Henry Cole) led by Captain Albert M. Hunter rode forty miles south from their base camp in Loudoun Heights through sleet and snow into Mosby’s Confederacy hoping to strike a blow against the troublesome guerilla warriors. The Union troops halted in Middleburg to camp for the evening before continuing on the following day to Rectortown, the heart of Mosby’s territory. They cautiously entered the eerily deserted town.

All along the way, Mosby’s men had intimidated their quarry through basic psychological warfare, riding around being “seen on every little hill and knoll” watching the Federals like hawks. To the invading Union troops, a Ranger seemed to lurk behind every tree and hill.

Their fears were realized as the recently minted commander of Mosby’s Company B, Captain Billy Smith, collected nearly three dozen Rangers to go after the Union troopers. Smith ambushed Hunter at Five Points, a junction where five country lanes converge about four miles from Rectortown. Forming a line of battle, the Union troopers occupied a strong position and fired their carbines at the oncoming horsemen, but many of the cartridges were damp from the inclement weather and misfired.

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Screaming as they charged into the Union flanks and rear, the Rangers unleashed a torrent of lead from their Colts. Smith’s second charge broke Hunter’s men. The Rangers routed the Federals, “killing, wounding, and capturing 57.” In the melee, Hunter was unhorsed and lay wounded and bruised on the ground. Two Rangers with empty pistols stood over him and demanded his weapons. The Union officer then hid himself behind a long and covered himself in leaves while the Confederates looked for his horse which had bolted away. “Here I was alone forty miles from camp on foot considerably hurt, and in an enemy’s country, and surrounded by the enemy. It was between 3 and 4 o’clock and in less than an hour turned awful cold.” A wet snow fell. Miraculously, the cavalry captain was able to hide from roving bands of Rangers and made the forty-mile trek back to Loudoun Heights on foot in the frigid weather only to come face-to-face with the Rangers again within a few days.

Fresh off their victory against Hunter, Mosby sought to vanquish Cole and his cavalry once and for all. A scout and elite member of the Confederate Secret Service, ninety-four-pound Frank Stringfellow, identified a weakness in Cole’s encampment: “[Cole had] no supports but infantry, which was about a one-half mile off.” Based on this intelligence, Mosby gathered some one hundred men and planned a surprise attack on the freezing night of January 9, 1864, in Upperville.

Johannes Adam Simon Oertel , 1866. Title: The Union Scout, Public Domain

Wrapped in blankets and bundled clothing to stave off frostbite and the frigid conditions, the group rode toward the northeast to Round Hill and stopped at Ranger Henry Heaton’s commodious estate, Woodgrove, for warm food and fire. “No sound broke the stillness of night except the dull, heavy tramp of the horses as they trod the snowy path. Fields, roads, and shrubs were alike clothed in the white robes of winter, and it seemed almost a sacrilege against the beauty and holy stillness of the scene to stain those pure garments with the lifeblood of men, be he friend or foe,” recalled Ranger James Williamson.

About two miles from the enemy camp, Stringfellow and his scouting party joined Mosby. A frontal assault up Harpers Ferry Road straight into Cole’s headquarters would have been a bloodbath. Instead, Stringfellow led the band north to the Potomac. They dismounted and led their horses in single file on foot through deep snow on a treacherous steep, narrow mountain trail following the river.

About 200 yards from the sleeping, unsuspecting camp, Mosby paused and ordered Stringfellow and a few other men to stealthily capture Cole and his staff, located in a two-story house 100 yards from the battalion’s bivouac area. Instead “the party sent with Stringfellow came dashing over the hill toward the camp, yelling and shooting. They made no attempt to secure Cole,” remembered Mosby.

Mistaking Stringfellow’s men for the enemy, the Rangers fired into the charging Confederates. Simultaneously, Mosby’s men fired into Cole’s tents. Cole had issued standing orders that if the Confederates attacked the battalion, his men were not to mount a horse so as to more clearly identify the enemy, and to “shoot every man on horseback.”

Cole’s men directed deadly carbine fire at the mounted Rangers. Deadly bloody combat ensued on both sides. Hunter described the chaotic nature of the melee: “Dark objects moving, some by the flash from the discharge of carbines, that was rapid for a few minutes. I do not think the whole thing lasted more than fifteen minutes, and when quiet was restored, it seemed as if an earthquake or some terrible convulsion of nature had swept over us and tore everything all to pieces.”

Crimson blood splattered the white snow. Several Rangers including one of Mosby’s original fifteen were mortally wounded. A signal gun from Harpers Ferry discharged, indicating Union reinforcements were on the march toward the besieged camp. Faced with mounting casualties, Mosby ordered his men to retire. As the Rangers tried to evacuate their wounded, more went down, including Billy Smith, as he tried to save young Charles Paxson who had been unhorsed by a hail of bullets. Alone and dying, Paxson had stammered, “Are you going to leave me here on the field?”

Ranger William Chapman remembered seeing Smith fall. “The flash from the volley for a moment blinded me and a feeling of thankfulness that we had escaped possessed me, when suddenly [Smith] leaped upright from the saddle and fell on the right side of his horse, his left foot drawing the stirrup over the right side and both of his feet hung in the stirrups with his head on snow.” The Ranger officer pulled Smith’s dangling body off the stirrups of his horse and placed his corpse in the snow.

Then like mist, the Rangers dissolved into the darkness. Union Captain Hunter remembered, “A moment’s reflection brought us to our senses, and a search for the enemy but always gone.”

The Confederate’s retreat to Woodgrove was filled with gloom; “sad and sullen silence pervaded our ranks and found expression in every countenance.” Mosby called it “one of the worst fights.” His Rangers suffered great losses—eight killed and several wounded who possessed invaluable leadership and experience. The Rangers’ strength stemmed from the exceptional skill and bravery of the men. “Even the Major [Mosby], though he usually appeared cold and unyielding, could not conceal his disappointment [tears ran down his face] and keen regret at the result of this enterprise. He knew and felt that he had suffered a loss which could not well be repaired.”

At dawn, the Federals surveyed the carnage. Hunter recalled, “We found Captain Smith, Mosby’s dashing leader, dead in front of Captain Corner’s tent, another near and a track of blood from behind my tent toward the road and 100 yd. off we found a dead man… A number of our men were wounded. Also, several of Mosby’s men fell into our hands.” One of those men was the mortally wounded Ranger Charlie Paxson. In his dying breath, Paxson asked for a Union soldier under Cole’s command, Samuel McNair. Months earlier Paxson’s mother, an ardent Southerner, had cared for the wounded McNair in their family home after he sustained wounds in a raid. After nursing him back to health, Paxson’s mother brought McNair back to Cole with an understanding that if her son, who rode with Mosby, needed the same care he would receive it. Hunter remembered that “Paxton [sic] asked for McNair and stated that fact to him. He got all of the kind attention that could be given to him, but his wound was fatal, and in a short time, he died.” A promise had been fulfilled on that cold, bloody night in January 1864.

Patrick K. O’Donnell is a bestselling, critically-acclaimed military historian and an expert on elite units. He is the author of thirteen books, including his new bestselling book on the Civil War The Unvanquished: The Untold Story of Lincoln’s Special Forces, the Manhunt for Mosby’s Rangers, and the Shadow War That Forged America’s Special Operations, currently in the front display of Barnes and Noble stores nationwide. His other bestsellers include: The Indispensables,  The Unknowns, and Washington’s Immortals.  O’Donnell served as a combat historian in a Marine rifle platoon during the Battle of Fallujah and often speaks on espionage, special operations, and counterinsurgency. He has provided historical consulting for DreamWorks’ award-winning miniseries Band of Brothers and documentaries produced by the BBC, the History Channel, and Discovery. @combathistorian