The county was founded on December 31, 1833. Tallahatchie is a Choctaw name meaning "rock of waters". The county is one of ten in Mississippi with two county seats, Charleston and Sumner. Charleston was the first county seat, and Sumner was organized later in 1872.
Charleston was founded in 1837, but its history antedates that. A settlement of five communities had grown up along the forks of Tillatoba Creek.
In 1833 the land was opened for settlement. There were only Indian trails at the time. Most of the settlers entered the county over what was called Charley's Trace, an Indian trail that came across from the Mississippi river and entered the hills about where Leverett is now located. Here the trail merged with a trail from the south and passed near the present site of Charleston.
Colonel Thomas Bailey came from Kentucky and formed the first settlement on the north fork of the creek which was about five miles to the northeast. He was later joined by James Bailey, Samuel Caruthers, William Flemming, M. Johnson, Willam Kendrick, Robert Thrasher, A. Patterson, and Kinchen Mayo who extended the settlement along the creek toward the Junction. Another settlement was started by the Priddys, the J. Houstons, Cade Alford and the Carson family who extended the settlement along the creek to the junction of three forks.
DeKalb and Tillatoba were founded on the north fork of the creek just west of the present town. Both towns wanted to be county seat of Tallahatchie, and Tillatoba succeeded. In 1837 the Board of Police found it necessary to abandon Tillatoba. There was a section of unsettled land in the heart of the first five settlements. This section of land had been granted to Greenwood LeFlore under the terms of the Dancing Rabbit Treaty of 1830. J.S. Topp & Co. had acquired this section of land and proposed to build the town of Charleston (named for Charleston, South Carolina) and to have this as the permanent county seat. In 1843 the county seat fight flared up again. The board voted to abandon Charleston, but Mr. Steel, the president of the Board of Police, refused to sign the minutes which killed the rally.
J.B. Sumner moved to this section in 1872 and founded what is now Sumner. The present site was a dense forest. He donated land for the railroad right-of-way, railroad park, courthouse square and jail lot. The next year Maria Church, a Presbyterian church, was erected. A post office was established in 1885 and the town incorporated in 1900.
From 1882 through 1884 disastrous floods and overflows of the river forced the people of Sumner to go by boat to Webb (which was at the time called Hood) for their supplies. From 1931 through 1933 there were overflows which inundated thousands of acres of farmland and destroyed much property.
The first court house was built in 1902 and destroyed by fire in 1908. The records were saved, but in 1909 the entire business section of the town burned and all records were destroyed.