The first school in Crestview was a two-story frame building. It opened in 1879 on Highway 85, where the cemetery is today. The names of some of the students who attended this school are still familiar today- Lance Richbourg, the Ferdon brothers, Opal Clark, R.D. Bush, and Alice Hart to name a few. At that time, the students went to school only four months out of the year.

The 1916, the original school was destroyed in a fire. Okaloosa County had just been formed and had appointed its first superintendent, W.G. Prior. Until they had a new school, the students were taught in a small church. The church stood where the Harris Building and the Church of Christ are today.

In 1917, the school was replaced by a small building across from the courthouse. It had only five rooms and seventy students. At that time, there were only two people in the faculty- Carey Rice (who was a principal, teacher, and a general handyman) and her assistant principal. This school had increasing enrollment until it was destroyed by a fire in 1920. After that, the students crammed into an old Baptist Tabernacle for classes.

Over the next six years, the county consolidated its school system. The schools went from sixty-four one-room buildings to fourteen larger institutions with more equipment and a varied curriculum. The first seniors graduated from Crestview in 1924. There were only three- Purl Adams, Julia Adams, and Alton Clary.

In 1926, there another new Crestview School was created. This one was located at Highway 90 and Ferdon Boulevard. In 1928, Crestview High School became an accredited institution. By 1937, it contained 200 students from grades one to twelve. The population of Crestview had reached 3,000.

During World War II, Eglin Air Force Base was built. The money from the national defense effort helped Okaloosa County progress. Education facilities were expanded and re-built. In 1942, Northwood Elementary School was built and grades one though and grades one through eight were moved there. Crestview High School then housed ninth through twelfth grade.

In 1953, disaster struck again, in the form of another fire. It was only a few hours before the students were going to be released for Christmas Break. So, another new school was built – the current Richbourg Middle School. It had 23 classrooms, a library, an office, a gym, a clinic and a lunchroom. The school cost $519,000 to build. There were 22 teachers that taught the 520 students enrolled there.

In 1969, Crestview High School had expanded so drastically that it was necessary for them to build another new CHS. This building is today’s Crestview High School. It now houses over 2000 students and 150 teachers and staff members.