The Battle of Fredericktown was fought on Oct. 21, 1861. Gen. M. Jeff Thompson set the stage for the Battle of Fredericktown in mid-October 1861 when he led the 1st Division, Missouri State Guard, to disrupt the Iron Mountain Railroad, the main Union artery from St. Louis into the southeastern Ozarks.
From a base in Stoddard County, Col. Aden Lowe and the State Guard infantry marched to Fredericktown while Thompson took his cavalry directly to the Big River railroad bridge. On Oct. 15, Thompson’s Missourians captured a company of Union bridge guards, burned the bridge and then scattered another company nearby at Blackwell’s Station.
On Oct. 16, Lowe reached Fredericktown. The next day, there was minor skirmishing with Union scouts. Thompson and his cavalry rode into the town later that day to support Lowe. He chased the Federal cavalry for a few miles and then turned back to Fredericktown. For the next three days, he remained there and gathered recruits. He also accumulated 18,000 pounds of badly needed lead from local mines.
Thompson and his brigade threatened Ironton, which prompted Brig. Gen. U. S. Grant, commanding in southeast Missouri, to send troops to dislodge the troublesome “Swamp Fox.” Federal columns soon converged on Fredericktown. Col. Joseph Plummer left Cape Girardeau on Oct. 18 with 1,500 soldiers. Two days later, Col. William P. Carlin, with 3,500 troops, marched from Pilot Knob to attack Thompson.
Learning of the dual Federal advance on the same day, Thompson decided to withdraw south to Greenville. With lead-filled wagons in front, the Missourians marched 12 miles before Thompson rashly decided to return to Fredericktown and give the larger Union force a fight. On the morning of Oct. 21, he placed his 1,200 men in concealed positions on both sides of the Greenville road south of Fredericktown and prepared to give battle.
On the same day, Carlin’s column reached Fredericktown and was told that the Missourians had left the previous day. Carlin, who was ill, decided not to give chase, pleading short rations. When the Cape Girardeau column arrived about noon, however, Plummer decided to pursue Thompson despite what he assumed was a long head start.
Taking a portion of Carlin’s units, Plummer started down the Greenville road. The cavalry advance had only proceeded a mile from town when they encountered Lowe’s guardsmen ahead, formed for battle behind a rail fence surrounding a cornfield. Plummer immediately deployed his troops to attack.
Thompson had planned only an ambush and quick retreat. He arranged his lines to support each other for a withdrawal. Lowe’s command, consisting of a regiment and two battalions, totaling some 500 men took position behind the fence and cornfield east of the Greenville road. Behind him was the four-gun battery that comprised the State Guard artillery. Across the road to the west, two infantry regiments held a line to the rear of Lowe’s cavalry and a small reserve force protected the flanks and rear.
Plummer ordered two guns of the Federal battery to unlimber on the Greenville Road and open a brisk fire. Thompson’s artillery responded in kind. Plummer deployed additional Federal units west of the road, including four more cannons under Maj. John Schofield. Part of Schofield’s battery and the 8th Wisconsin Infantry were held in reserve.
Plummer sent the 17th Illinois and 11th Missouri infantry regiments into the cornfield to attack Lowe’s position. The Federal skirmishers encountered heavy musket fire and were twice driven back by the Missourians. The 20th Illinois was thrown into the fray. For 40 minutes, the fighting raged. State Guard casualties mounted and the Federals began to flank their position. Lowe was supposed to fall back at this point, but recklessly fought on until he was shot dead. In the face of well aimed artillery fire and superior numbers, the Guardsmen, at last, retreated. Union rifles exacted a heavy toll as the Missourians raced for their reserve line. Seeing the enemy’s overwhelming numbers, Thompson ordered a withdrawal down the Greenville road, leaving behind several killed and wounded and a damaged cannon.
Hoping to rout the retreating Missourians, Plummer ordered the 1st Indiana Cavalry to charge. But, Thompson had anticipated such a move and had set an ambush. As the Indiana Cavalry thundered down the road, soldiers of Thompson's command suddenly arose from concealment and unleashed a volley that killed 4 cavalrymen, including Maj. John S. Gavitt and Capt. John K. Highman, and left 28 wounded. The Indianans wheeled in retreat while the Missourians hurried down the Greenville Road without serious pursuit.
Elated by success, the Federals returned to Fredericktown. Angry soldiers, suspecting the hapless townspeople knew of Thompson’s ambush, burned eight dwellings and looted the courthouse and Catholic Church before the rampage was halted.
Federal losses in the battle tallied 14 killed and 60 wounded. Reports of Thompson’s casualties vary, but his known losses totaled 17 killed, 52 wounded, and 78 captured, including 38 wounded.
Although it was a tactical victory for the Union, the battle had no important strategic effect on the war in southeast Missouri. Each side simply returned to their posts to await another opportunity.