In mid-October 1861, Gen. M. Jeff Thompson led the 1st Division of the Missouri State Guard into action to disrupt the Iron Mountain Railroad, the main Union route from St. Louis into the southeastern Ozarks. After Thompson's troops captured Union bridge guards, burned the Big River railroad bridge, and scattered another company at Blackwell's Station, Col. Aden Lowe and State Guard infantry reached Fredericktown while Thompson's cavalry joined them there. Thompson gathered recruits, collected 18,000 pounds of lead from local mines, and threatened Ironton, prompting Brig. Gen. U.S. Grant to send Federal forces under Col. Joseph Plummer and Col. William P. Carlin against him. As the two Union columns converged, Thompson began to withdraw south but then returned and on Oct. 21 placed about 1,200 men in concealed positions along the Greenville road south of Fredericktown. When Plummer pursued with part of Carlin's force, his advance encountered Lowe's men behind a rail fence and cornfield. Thompson had arranged his lines for an ambush and retreat, with Lowe's command east of the road, artillery behind them, and additional infantry west of the road. Federal artillery opened fire, more guns were brought up under Maj. John Schofield, and Union infantry attacked through the cornfield. Lowe's men twice drove back the attackers, but after about 40 minutes of fighting, mounting casualties and a Federal flanking movement forced the State Guard back. Lowe, who should have withdrawn, continued fighting until he was killed. Thompson then ordered a retreat down the Greenville road, leaving behind several killed and wounded and a damaged cannon. When Plummer sent the 1st Indiana Cavalry in pursuit, Thompson's concealed men sprang an ambush that killed four cavalrymen, including Maj. John S. Gavitt and Capt. John K. Highman, and wounded 28, allowing the Missourians to escape without serious pursuit. The Federals returned to Fredericktown, where angry soldiers burned eight dwellings and looted the courthouse and Catholic Church before being stopped. Federal losses were 14 killed and 60 wounded; Thompson's known losses were 17 killed, 52 wounded, and 78 captured, including 38 wounded. Although the battle was a tactical Union victory, it had no important strategic effect in southeast Missouri, and both sides soon returned to their posts.
