Following the War of 1812, soldiers returning home by boat from New Orleans stopped at Wellington, and some remained as settlers.

In 1838, Judge Joseph McGuire—one of the earliest settlers and owner of a plantation next to Wellington—was given a contract to cut a road, and a house was purchased for $500 which became the courthouse.

Just prior to the Civil War, Prentiss had several buildings, a racetrack, a good hotel, and a newspaper, the Bolivar Times.

During the Civil War, Confederate soldiers would move east by foot from Napoleon, Arkansas, hide in a wooded area near the bend, and then fire on passing Union ships.

Following one such ambush in 1863, a Union gunship led by William Tecumseh Sherman landed at Prentiss and burned the town to the ground.

The Napoleon Channel improved the Mississippi River for shipping, as it removed 10 mi (16 km) from the navigable route.