In 1925 on a site east of the present Bolivar Middle School, the Julius Rosenwald Foundation built and operated a school known as Bolivar Industrial School. The building, which presently houses Bolivar Middle School, was completed in 1959.

As a result of the county desegregation and consolidation plan, in 1970 Bolivar Industrial School became Bolivar Junior High, serving grades seven, eight, and nine. The ninth grade received students from Whiteville, Toone, and Hornsby. The Southern Association of Colleges and Schools first accredited Bolivar Junior High School in 1976. An extensive countywide building program began in 1996 that added five classrooms to the existing twenty-seven.

The new wing was utilized in 1998 when Bolivar Junior High became Bolivar Middle School, serving grades six, seven, and eight. At this time the ninth grade was moved to Bolivar Central High School, making Bolivar Middle the largest of four feeder schools to the high school, and the sixth grade was moved from Bolivar Elementary School.

Bolivar Middle School is a Title I school providing services to all students, and it utilizes a variety of instructional programs to support the curriculum. The school day consists of six class periods. The class periods include five academic classes of Language Arts, Reading, Social Studies, Math, and Science, and one exploratory class or Band.  There are four exploratory classes:  Technology Engineering, Physical Education, STREAM, and Keyboarding. The students change exploratory classes every nine weeks. Students are also offered the option to participate in the band program in place of their exploratory classes.