Okolona was a Civil War engagement fought in Mississippi, 1864. It was a Confederate victory.
From Vicksburg, Mississippi, Sherman launched a campaign to take the important railroad center at Meridian, Mississippi, and if the situation were favorable, to push on to Selma, Alabama, and threaten Mobile. Sherman ordered Brig. Gen. William Sooy Smith to lead a cavalry force of 7,000 men from Memphis, Tennessee, on February 1, 1864, south through Okolona, along the Mobile & Ohio Railroad, and to meet the rest of the Union force at Meridian, on February 10. With the main force of approximately 20,000 men, Sherman set out on the 3rd for Meridian, but made feints on various other locations. Against orders, Smith delayed ten days, while waiting for reinforcements, and did not start out until February 11. Destroying crops and railroad track along the way, Smith's force met almost no opposition, and, before long, 1,000 former slaves were traveling with them. Smith was supposed to rendezvous with Maj. Gen. William T. Sherman at Meridian on the 10th, but he never arrived there. Sherman left Meridian on the 20th, due in part to apprehension over Smith's whereabouts. Smith neared West Point, 90 miles north of Meridian, on the 20th, and he fought with Confederate cavalry units at Prairie Station and Aberdeen. Smith-knowing that Nathan Bedford Forrest commanded the troops he was fighting, concerned about the fate of the former slaves with him, and not knowing how many of the enemy he faced-decided to concentrate at Prairie Station, and, on the morning of the 21st, he set out for West Point. Shortly after dawn on the 21st, Col. Jeffrey Forrest's Confederate cavalry brigade engaged Smith. Withdrawing at times, Forrest drew Smith into a swamp west of the Tombigbee River. Other Rebel troops arrived and the fighting intensified. Smith was sure that this was a trap set for him, and, discerning that he was greatly outnumbered, he ordered a retreat, leaving a rearguard. The rearguard held off the Confederates for about two hours before withdrawing in good order. About the same time, Maj. Gen. Nathan Bedford Forrest arrived and ordered a pursuit. Skirmishing occurred the rest of the day. At sunup on the 22nd, the Rebels attacked Smith just south of Okolona on the prairie. More Confederate troops arrived, causing breaks in the Union battle line, precipitating a retreat. For most of the rest of the day, they engaged in a running battle for a distance of eleven miles, with both sides attacking and counterattacking. Col. Forrest was killed during one Rebel charge. The Yankees finally broke off the fighting and headed for Pontotoc. Maj. Gen. Nathan Bedford Forrest, the commander on the field, realized that his men were nearly out of ammunition and did not order a pursuit. Mississippi militia harassed Smith to the state line. Smith arrived in Collierville, Tennessee, near Memphis, on the 26th. Although Smith had caused much destruction during his expedition, Okolona forced him to retire before he could do more. Smith's actions against Sherman's orders jeopardized the Meridian Expedition.
On February 22, 1864, Confederate and Union troops clashed at Okolona, in Chickasaw County, Mississippi, in one of the many engagements of the American Civil War. Major-General Nathan B. Forrest led the Confederate horsemen against a Union cavalry contingent of more than 7,000 men under Brigadier-General William S. Smith, and the Confederates carried the field, inflicting 100 casualties while suffering 50 of their own.
Smith had received orders to march out of Memphis, Tennessee, and join up with Major-General William T. Sherman's much larger army, some 20,000 strong, which was advancing on Meridian, Mississippi. Instead of complying promptly, Smith held back his march for ten days, waiting for a unit trapped by ice in Kentucky. Once he finally got underway, his column ran into Forrest's cavalry on February 21, and the following day the two sides fought a running engagement stretching across eleven miles. Bolstered by reinforcements, Forrest broke Smith's force and sent it fleeing, though a shortage of ammunition kept him from chasing the beaten Federals any further. Smith's battered command crossed into Tennessee on February 26, and afterward he faced sharp criticism for having jeopardized Sherman's Meridian campaign through his delay.
Because it served as a crucial railroad hub, Meridian became the target of a Union campaign that Sherman set in motion from Vicksburg, Mississippi, starting on February 3. He led 20,000 troops to the edges of the town. Meanwhile, seven thousand cavalrymen under Smith's command, stationed in Memphis, received orders on February 1 to march toward Meridian along the Mobile & Ohio Railroad, with a planned meeting with the main Union army set for February 10. Sherman used feints to mislead Confederate defenders about his true direction, but Smith held back his own departure for ten days, finally setting out on February 11. His troops encountered no resistance as they crossed the countryside, tearing up railroad lines, ruining crops, and gathering roughly 1,000 freed slaves along the way. Muddy conditions hampered his progress by February 16, when he reached New Albany. Two days later, on February 18, his men pushed Confederate defenders out of West Point. By February 20, Smith's column stood just 90 miles from Meridian, near West Point, right as Sherman abandoned the town and headed back to Vicksburg, worried about Smith's unknown location. Upon learning of Sherman's withdrawal, Smith reversed direction and set his sights on Okolona.
That same day, February 20, Smith clashed for the first time with Forrest's Confederate troops near Prairie Station and Aberdeen. The following day, worried both about the strength of the opposing force and what might happen to the freed slaves if captured, Smith chose to pull back toward West Point. During this retreat, a Confederate cavalry brigade led by Colonel Jeffrey E. Forrest drew him into the marshy terrain surrounding the Tombigbee River. Smith once again had to fall back, leaving behind a rearguard that did not rejoin his main body until two hours afterward.
As the rearguard began pulling back, Forrest reached the scene and took charge of the fighting, opening the engagement with an assault at first light on February 22 across the open prairie south of Okolona. The Union troops had gotten off their horses and thrown up barricades to defend their position. Striking straight ahead while also probing the flanks, Forrest's men, bolstered by fresh Confederate troops, tore openings in the Union line and forced a broader withdrawal, leaving five cannons behind on the field.
Pulling back to a ridge, the Union soldiers regrouped, and amid a series of charges and countercharges, Col. Forrest, younger brother of the major general, took a fatal wound to the neck. Legend holds that he died in his brother's arms, with the older Forrest repeating only "Jeffrey, Jeffrey." The Confederate momentum stalled briefly after the colonel fell, but the major general rallied his men, personally leading a charge meant to "exact vengeance" and shatter the Union line. As they pressed the pursuit, Forrest's party was momentarily surrounded, until Col. McCullough arrived with additional troops to relieve them.
What followed was an eleven mile running fight as the retreating Union forces tried to hold a succession of positions, using plantations and makeshift roadblocks for cover. None of these held for long against the Confederate advance. By late in the day, the Union troops had formed three lines across an open field and launched charges against the Confederates, who broke both assaults with volley fire delivered at a distance of forty yards. With his men beaten back, Smith ordered another retreat. Forrest, running low on ammunition, called off the chase soon after, though Smith still had to fight through other Mississippi militia forces during the remainder of his march toward the Tennessee line.
Smith finally crossed into Tennessee with what remained of his command on February 26 at Collierville, where he faced criticism for having ignored his original orders to march toward Meridian on February 1. His health in decline, Smith resigned from the army in September 1864 and went back to civilian life.
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