Choctaw Indian legends say the tribe originated at Nanih Waiya in what is now the extreme southeastern part of Winston County.
A large mound at Nanih Waiya is a sacred place to the Choctaws and is preserved today as a Mississippi State Park.
Winston County is one of 16 Mississippi counties formed in the 1830s from lands ceded to the United States in September 1830 by Chief Greenwood LeFleur, the Chief of the Choctaws, in the Treaty of Dancing Rabbit Creek. Soon after the treaty was signed, most of the Choctaws were removed to what is now the State of Oklahoma.
The few Choctaws who remained in Mississippi after the 1830 treaty were the direct ancestors of the Mississippi Band of Choctaw Indians, today one of the most prosperous and progressive Indian tribes in America.
Winston County was established December 23, 1833. Louisville was charted in 1836. Both were named for the same man, Louis Winston, a Natchez lawyer then prominent in Mississippi politics.
Colonel Louis Winston (1784-1824), a native of Virginia, moved to the Mississippi Territory and became a prominent lawyer and the colonel of a regiment of militia. In 1809 he was appointed the district attorney general for Madison County, but it appears that he moved to the Natchez District in about 1817. He was the secretary of the Constitutional Convention of 1817, and he served as a judge of the Mississippi Supreme Court from 1821 until his death, on August 20, 1824, at his home in Washington, Mississippi.
By the start of the American Civil War, Louisville was a prosperous city, serving as a regional commercial center.
Although there were no Civil War battles fought in Winston County, more than 400 Winston County men died in the service of the Confederacy during the war.
Several prominent Winston Countians lost fortunes loaned to the Confederacy.
Union Colonel Benjamin H. Grierson marched his 900 troops through Louisville on April 22, 1863 while on his famous "raid" through the heart of Mississippi. Grierson's troops camped for the night in Winston County.
There was no fighting. Having been spared from significant destruction of property, Louisville and Winston County recovered earlier than some other places in the South and continued to grow after the war.
Much of Winston County's economic strength, starting from the earliest years of the 20th century, came from the plentiful growth of timber. The timber industry and industries closely allied to it continue today as the back bone of the local community, as witnessed by the large Georgia Pacific Plant and other industries.
