Originally located in Carroll County, Middleton was one of the earliest settlements in the area.

In 1790 he built a small log store used for trading with the Choctaw, whose territory this was, and with the occasional traveler.

[3] Following the Treaty of Dancing Rabbit Creek with the United States in 1830, most of the Choctaw from the area were removed to west of the Mississippi River in Indian Territory.

The "Little Log Store", located at the junction of the Carrollton and Shongalo roads, became a well-known trading post.

[5] As a result of being bypassed, Middleton was abandoned in favor of the new railway town of Winona, which was designated as the county seat.

[3] During the Civil War, the town's mills were converted to manufacture products for the Confederate army.

[3] Benjamin Grierson and about 1,000 Union soldiers camped near Old Middleton before traveling to nearby Vaiden on January 1, 1863.