Fredericktown was a Civil War engagement fought in Missouri, 1861. It was a Union victory.
Two Union columns, one under Col. J.B. Plummer and another under Col. William P. Carlin, advanced on Fredericktown to overtake Brig. Gen. M. Jeff Thompson and his men. On the morning of October 21, Thompson's force left Fredericktown headed south. About twelve miles out, Thompson left his supply train in a secure position and returned toward Fredericktown. He then learned that Union forces had occupied Fredericktown, so Thompson spent the morning attempting to discern the enemy numbers and disposition. Unable to do so, he attacked anyway, around noon. Plummer, with his force and a detachment of Col. William P. Carlin's troops, met the Rebel forces outside town and a two-hour fight ensued. Overwhelming Union forces took their toll, and Thompson's men retreated. Union cavalry pursued. Fredericktown cemented Union control of southeastern Missouri.
On October 21, 1861, Union and Confederate forces clashed in Madison County, Missouri, in what became known as the Engagement at Fredericktown, sometimes called the Battle of Fredericktown. The fighting ended in a Union triumph, one that helped secure the southeastern part of the state firmly under Union control.
In October 1861, M. Jeff Thompson, a brigadier-general in the Missouri State Guard, marched a force of 1,500 men into the southeastern part of the state. His troops set fire to the Iron Mountain Railroad bridge spanning the Big River in Jefferson County on October 15, an action that also netted the capture of numerous soldiers guarding the span. In response, the Union dispatched two columns after him: one led by Col. Joseph B. Plummer, numbering 1,500 men, and a second under Col. William P. Carlin, comprising 3,000. Word of this pursuing force reached Thompson by October 20, prompting him to pull his men back to a position south of Fredericktown. Despite this retreat, he changed course that same evening and resolved to send his infantry against the approaching Federal troops.
Before dawn Thompson worked to gauge how many enemy troops faced him and how they were arranged, but the information eluded him. Rather than advance blindly, he arranged his men and guns along the roadway in a concealed position and waited for the Federals to arrive. Most of his Missouri State Guard troops stayed out of sight atop wooded heights shaped like a U that looked down over the road. Positioned ahead of this main line, Col. Aden Lowe's infantry regiment sat exposed in a cornfield, serving as a lure. A 12-pounder cannon waited just behind them for support, while three more 6-pounders were stationed farther back and off to the side.
Plummer's column reached the scene around midday, accompanied by a detachment from Col. William P. Carlin's command. The first shots came from Capt. Stewart's company of Illinois cavalry. Col. Ross then sent his 17th Illinois Infantry against Lowe's men, opening with skirmishers before committing the full regiment. Union guns opened fire on the Missourians' 12-pounder, which fired back. Meanwhile the 20th Illinois and 11th Missouri pressed in on both sides of Lowe's position as additional Union cannon joined the fight. Lowe lingered too long before pulling back and was struck fatally in the head; what remained of his regiment fled after suffering severe losses.
Seeing the abandoned 12-pounder, the 1st Indiana Cavalry tried to run it down and seize it, but Thompson's men, firing from both ridgelines, drove them back with heavy losses. The cavalry called for infantry help, and the 17th Illinois rushed forward to claim the gun once the Missourians had left it. As still more Union infantry arrived on the field, Thompson set his guardsmen to an orderly retreat. He managed this withdrawal successfully for the most part, aside from a portion of his cavalry that broke and ran.
Certain Union troops suspected that townspeople had lent Thompson a hand during the fighting. Their anger deepened over what they saw as mistreatment of Unionist citizens along the route they had marched. Out of this bitterness came a wave of vengeance against the town, carried out by common soldiers rather than their commanders. Before officers managed to reassert discipline, at least seven houses in Fredericktown had gone up in flames, and additional structures suffered damage.
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