During Gen. Nathan Bedford Forrest’s cavalry raid through West Tennessee in December 1862 and January 1863, his brigade approached Trenton as Union Col. Jacob Fry prepared to resist. Although Fry had fortified the high ground overlooking the town, orders sending most of his force to Jackson left him with only 250 convalescents, stragglers, fugitives, and other soldiers, enough only to defend the Mobile and Ohio Railroad depot, which he barricaded with cotton bales. On December 20, Fry placed 25 sharpshooters in a brick building across the street behind a parapet on the roof, six more in the windows of another brick building, and others in a nearby stockade. When Forrest’s men rode into town at 3:00 that afternoon, the Union defenders opened fire from the buildings and other positions. The Confederates moved out of range, surrounded the Union position, and shelled it from the earthworks Fry had constructed. Fry surrendered, believing Forrest could quickly destroy the stockade and depot and inflict heavy losses while his own men, armed only with old guns and without bayonets, could do little damage. Forrest reported two men killed and seven wounded on his side and claimed the Federals lost two killed and seven hundred prisoners. The Confederates captured and destroyed military stores and took several hundred cavalry horses, keeping those in good condition and giving the rest to the town’s residents. The next morning Forrest paroled the prisoners and continued toward Union City.