Before 1900, the future Chesapeake School District had twelve schools: Bethel, Bear Creek, Big Branch, Chesapeake Central, Upper Chesapeake, Coryville, Ranking Creek, Red Oak, Union, Getaway, Henson Hollow, and Bradrick. The Bethel School, located next to Methodist Church at Bethel, was a one-room building that held eight grades. Chesapeake Central had six rooms and was located at the foot of the 6th Street Bridge in Chesapeake. A two-roomed school located on Rockwood Avenue in Chesapeake was named Upper Chesapeake. Bradrick School was located on Bradrick Hill in Bradrick and had two rooms.
The first high school was formed in 1921 after overcrowding at Central Junior High School in Huntington caused ninth grade students to be sent home. Fraternal Hall Building originally housed the one room school. The one room was used as a classroom, gynasium, and a study hall. Willard McDaniel taught classes with no modern heating and lighting. A second teacher, John Dillon, was added in 1922. The first graduation ceremony was held in 1924 at the Christian Church.
In 1925, nine students graduated and the first high school building was ready for use. Ten more rooms were added to the high school building in 1948 to house the elementary grades.
1956 saw two new buildings built, a new high school and a new elementary. At that time, the school district boasted three schools: East Elementary, West Elementary, and Chesapeake High School. In 1989, East Elementary was replaced by a new high school building.