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Situated near the eastern border of Chickasaw County, the city of Okolona, Mississippi is one of two county seats, the other being Houston. It is uncertain precisely when the community was founded, but it was known as Rose Hill in 1845. However, when a post office was established in 1850, it was found that another town had that name, so it was named Okolona, supposedly the name of a Chickasaw warrior. By the mid-1800s, Okolona and the surrounding Black Prairie Region, also known as the Black Belt or the Prairie Belt, became what would be known as the Bread Basket of the Confederacy, and was part of the original Cotton Belt before it was supplanted by the Mississippi Delta Region. The Mobile and Ohio Railroad came through in 1859, and much of the town grew up along the rail line. Okolona suffered greatly during the Civil War, as it was the site of five skirmishes or battles, the most significant being the Battle of Okolona, which occurred on February 22, 1864, with Brigadier General William Sooy Smith commanding 7,000 Union cavalry troops, and Major General Nathan Bedford Forrest commanding 2,500 Confederate cavalry. The result was a Confederate victory, with 388 Union and 144 Confederate casualties or losses. Among the dead was General Forrest’s brother, Jeffrey. Due to a lack of ammunition, Forrest decided not to pursue the retreating Union troops, however. Most of the buildings and businesses in Okolona did not survive the war. A few did, including the Elliot Donaldson House, which is listed on the National Register of Historic Places. Okolona College, founded in 1902, was a college for African Americans, and is now part of the Okolona College Historic District, also on the National Register. The columnist, William Raspberry, was born in Okolona, as was Milan Williams, keyboardist and composer for The Commodores.



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