Howell County was organized on March 2, 1857, from Oregon County, and is named for Josiah Howell, who made the first settlement in Howell Valley.
The first Circuit Court met in a log cabin one mile east of West Plains, according to an 1876 account. A small, wooden courthouse was built on the square in West Plains in 1859. It was damaged during the Civil War in 1862. The county was reorganized three years later, but all of the county records were destroyed in an 1866 fire. A second courthouse was built in West Plains in 1869. It was a small, three-room, frame building, about 24 by 30 feet.