During the Civil War, Tompkinsville was the site of Confederate General John Hunt Morgan's first Kentucky raid. July 9, 1862, Morgan's Raiders, coming from Tennessee, attacked Major Thomas J. Jordan's 9th Pennsylvania Cavalry. Raiders captured 30 retreating Union soldiers and destroyed tents and stores. They took 20 wagons, 50 mules, 40 horses, sugar and coffee supplies. At Glasgow, Kentucky they burned supplies, then went north, raiding 16 other towns before returning to Tennessee.