Confederate guerilla leader John Singleton Mosby and his intrepid Rangers are known for their incredibly daring feats, but they weren’t always successful. One cold night in the winter of 1864, Union cavalry troops were surprised by a Confederate raid and suffered a bloody defeat.
On December 30, about 80 men of Capt. Albert M. Hunter’s Cole Cavalry (or the 1st Regiment, Potomac Home Brigade, named for its commander, 29-year-old Maj. Henry Cole) marched 40 miles south from their base at Loudoun Heights in sleet and snow and charged into Mosby’s Confederate forces hoping to strike a blow against the pesky guerrilla fighters. The Union forces rested for the night in Middleburg and then headed the next day for Rectortown, the heart of Mosby’s territory. They entered the eerily deserted town cautiously.
All along the way, Mosby’s men used basic psychological warfare to intimidate their targets, appearing on every hillock and knoll and watching the Union troops like hawks. To the invading Union troops, it seemed like a Ranger was lurking behind every tree and hill.
Their fears were realized when Captain Billy Smith, who had recently taken command of Mosby’s Company B, assembled nearly 30 Rangers to pursue the Union soldiers. Smith ambushed the hunters at Five Points, a crossroads of five country roads about four miles from Rectortown. The Union soldiers formed into strong lines and fired their carbines at the approaching cavalry, but much of their ammunition was damp from the bad weather and misfired.
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The Rangers charged the Union flank and rear, shouting, firing a torrent of lead from their Colts. Smith’s second charge destroyed Hunter’s force. The Rangers routed the Union troops, “killing, wounding, and taking prisoner fifty-seven men.” In the melee, Hunter fell from his horse and lay wounded on the ground. Two Rangers with empty pistols stood over him and demanded his weapon. The Union officer hid behind a long tree and covered himself with leaves while the Confederates searched for his fleeing horse. “Here I was, walking alone, forty miles from my camp, much wounded, and surrounded by enemies in enemy territory. Between three and four o’clock, and in less than an hour it was bitterly cold.” A wet snow fell. Miraculously, the cavalry captain hid from the Rangers’ pursuit and walked forty miles in frigid weather back to Loudon Heights, only to encounter the Rangers again within a few days.
Shortly after his victory over Hunter, Mosby attempted to wipe out Cole and his cavalry. Frank Stringfellow, a 94-pound elite Confederate Secret Service agent, identified a weak spot in Cole’s position.[Cole had] “There was no support except for the infantry about a half mile away.” Based on this information, Mosby gathered about 100 men and planned a surprise attack on Upperville on the frosty night of January 9, 1864.
Wrapped in blankets and thickly wrapped to ward off frostbite and the frigid weather, the group headed northeast toward Round Hill, stopping at Ranger Henry Heaton’s spacious estate, Woodgrove, for a hot meal and a fire. “No sound broke the silence of the night but the dull, heavy thud of our horses tramping through the snow. The fields, roads, and bushes were all clothed in the white garments of winter, and to stain their pure garments with the blood of any human being, friend or foe, seemed an almost desecration of the beauty and sacred serenity of the landscape,” Ranger James Williamson recalled.
About two miles from the enemy positions, Stringfellow and his scouts joined Mosby. Instead of heading straight up Harpers Ferry Road and launching a frontal attack on Cole’s headquarters, which would have resulted in a bloody battle, Stringfellow instead led his men north to the Potomac River. They dismounted and led their horses in single file through deep snow on a steep, narrow mountain trail alongside the river.
About 200 yards from the sleeping and unsuspecting camp, Mosby stopped and ordered Stringfellow and several other men to sneak up on Cole and his staff in a two-story house 100 yards from the battalion camp. However, “the men sent with Stringfellow charged over the hill toward the camp, screaming and firing. They made no attempt to secure Cole,” Mosby recalled.
The Rangers mistook Stringfellow’s men for the enemy and opened fire on the charging Confederates, while Mosby’s men fired into Cole’s tents. Cole had issued standing orders that if any Confederates attacked his battalion, his men were to remain unmounted and “shoot every man that is on a horse” so they could get a clear view of the enemy.
Cole’s men opened fire with their carbines on the mounted rangers. A bloody, deadly battle ensued on both sides. Hunter described the chaos of the melee: “Dark objects were moving, some of them with the flashes of our carbines, and moving rapidly for several minutes. I think this state of affairs lasted no more than fifteen minutes. When calm returned it was as if an earthquake, or some terrible act of nature, had swarmed us and tore everything to pieces.”
Bright red blood splattered onto the white snow. Several Rangers were mortally wounded, including one of Mosby’s 15 original men. A signal gun was fired from Harpers Ferry indicating Union reinforcements were marching toward the besieged camp. Seeing the casualties mounting, Mosby ordered his men to retreat. As the Rangers tried to evacuate the wounded, more were killed, including Billy Smith, who tried to save young Charles Paxson, who had fallen from his horse in a hail of bullets. Alone and dying, Paxson stammered, “Are you going to leave me on the battlefield?”
Ranger William Chapman remembers seeing Smith fall: “The flash of the volley blinded me for a moment, and then a feeling of gratitude came over me that I had escaped. Suddenly… [Smith] Smith jumped straight out of the saddle and fell over the right side of the horse, his left foot pulling the stirrup over to the right side, both feet hanging in the stirrup and his head above the snow. ” Ranger officers pulled Smith’s hanging body out of the horse’s stirrups and placed the body in the snow.
Then, like a mist, the Rangers vanished into the darkness. Union Captain Hunter recalled, “I thought for a moment, came to my senses, then looked for the enemy, but they were always gone.”
The Confederate retreat to Wood Grove was filled with gloom. “A sad and sombre silence pervaded our ranks and was expressed in every countenance.” Mosby called it “one of the worst battles.” His Rangers suffered heavy losses: eight men killed and several wounded, all of whom possessed valuable leadership and experience. The Rangers’ strength came from the exceptional skill and courage of their soldiers. “Even the major [Mosby]Although he always came across as cold and stubborn, he could not hide his disappointment. [tears ran down his face] and he felt deep regret at the outcome of the enterprise. He realized and felt that he had suffered an irreparable loss.”
At daybreak, the Union troops surveyed the devastation. Hunter recalled, “We found the body of Capt. Smith, Mosby’s brave leader, in front of Capt. Corner’s tent; another was nearby, with a trail of blood running from the rear of my tent down to the road, about a hundred yards away. Several of our men were wounded, and several of Mosby’s men were also lost to us.” One of these was mortally wounded Ranger Charlie Paxson. As he lay dying, Paxson asked for Samuel McNair, a Union soldier under Cole’s command. A few months earlier, Paxson’s mother, a staunch Southerner, had nursed McNair back to health, and brought him back to Cole, promising that if her son, who had been riding with Mosby, needed the same care, Paxson would do so. Hunter wrote, “Paxson was a great man, and he … [sic] “I visited McNair and conveyed the facts to him. He received all the kindest treatment he could receive, but his wounds were fatal and he soon died.” And so the promise was fulfilled on that cold, bloody January night in 1864.
Patrick K. O’Donnell is a bestselling and acclaimed military historian and expert on elite military forces. He is the author of thirteen books, including a new bestselling book on the Civil War. The untold story of Lincoln’s Special Forces, Mosby’s Ranger Hunt, and the shadow war that gave birth to American special operations, It is currently on display in Barnes & Noble stores nationwide. His other bestsellers include: Must-Haves, Unknown Peopleand Washington ImmortalsO’Donnell served as a combat historian for a Marine rifle platoon during the Battle of Fallujah and is a frequent speaker on espionage, special operations and counterinsurgency. He has served as a historical consultant on DreamWorks’ award-winning miniseries Band of Brothers, as well as documentaries produced by the BBC, the History Channel and Discovery. PatrickKODonnell.com translation:





