Middleton is a defunct town in Montgomery County, Mississippi. Middleton was originally located in Carroll County. It was incorporated into Montgomery County in 1871, following the formation of the county. The town was one of the area's first settlements. Middleton was well-known for his commercial and educational success.

Rise of Middleton

Irelton C. DeVane, a European American, was the first settler at the site. In 1790, he was able to construct a small log store where people could trade. In the 1920s, he was joined by Kentucky residents such as William Pace and his wife. They were later joined by other European-Americans who were forced to settle the land. Some of them were accompanied by African American slaves. As the population grew, the small log store grew into a well-known trading post. Two doctor's offices, two general merchandise stores, a furniture maker, a tavern, a shoe factory, a tailor, and a clock shop were among the various businesses established during the 1830s. Baptist, Methodist, Presbyterian, and Christian churches were established by the town's settlers. The town was incorporated as Irwin in 1837, but the name was changed to Middleton in 1840.

The town's population grew rapidly, and by 1840, it numbered 2,900 people. In 1843, a newspaper called 'The Family Organ' was published. In the thriving commercial center, the Middleton Hotel, a photographer's shop, a blacksmith shop, law offices, and a carriage factory were later established. Industries sprang up along the river's banks to harness its power. The town had built businesses such as a wool mill, flour mill, cotton mill, cotton factory, and leather tannery on its outskirts. The town had a cemetery surrounded by a deep ditch that resembled a moat. There were also two private schools in town: Judson Institute, a female academy, and The Peoples Academy, a boy school.

Cut off

Mississippi Central Railway built one of its rail lines through Winona in 1859. Winona was a city close to Middleton. The bypassing of the railway line was detrimental to Middleton because it drove operating businesses and residents to the new railway town of Winona. Some of the families who had settled in town returned to Tennessee and Kentucky. During the Civil War, the town mills were converted into a manufacturer of products for the Confederate army. Before abandoning the old Middleton, Benjamin Grierson and about 1000 Union soldiers camped nearby.

On January 1, 1963, the soldiers arrived in Vaiden, having taken almost everything in the town. The town had been abandoned and deserted. Currently, only a small portion of the town remains. In 1992, the Lions Club of Winona restored the cemetery's significant remains. The cemetery is considered to be one of the oldest in the country.