Throughout the Civil War, Confederate forces were stationed in Okolona to take advantage of the agriculturally rich prairie region, and with a large supply depot the town became the object of Union raids at least twice. On February 22, 1864, Maj. Gen. William Sooy Smith's expedition was defeated by Nathan Bedford Forrest's cavalry in a day-long battle. Later, in December, Benjamin Grierson, commanding a cavalry raid down the Mobile and Ohio Railroad, occupied and burned much of the town of Okolona.
