Education in the Western Branch area has had a long and vibrant history. Heeding Thomas Jefferson's pleas for public education in Virginia, the 1799 Virginia Assembly established four schools in the state, two of which were in Tidewater. One of these, the Craney Island School was the direct ancestor of Western Branch High School.

The local name of "Churchland" was given to a school in 1854. This Churchland School, consisting of grades one through eleven, moved in 1922 to a three-story brick structure. By 1950, the area's truck farms had given way to housing developments, and the present Churchland High School was built to accommodate the expanding school population. In 1961, the City of Portsmouth initiated annexation proceedings for the entire area, then under the jurisdiction of Norfolk County, with the City of South Norfolk to form the new corporate City of Chesapeake. This area became the City of Chesapeake by popular vote in January, 1963. When the final distribution of the area took place in 1968, Chesapeake received the building which was to become the first Western Branch High School. Thus Western Branch High School, comprised of 1,200 students in grades six through twelve, began in the new city of Chesapeake on September 3, 1968.

Further community growth resulted in the need for a larger high school building; the present Western Branch High School building was first occupied in September, 1972. In 1988, an addition was constructed to the school adding twelve classrooms in order to accommodate the growth of the community. In 1997, a second addition and renovation of the original building was initiated and completed shortly thereafter. Construction of another addition consisting of 70,000 square feet and renovation of the existing building will be completed in 2011.

Mr. William J. Peale served as the first principal and remained in that post until 1970. Mr. Arthur V. Brandriff, Jr. was then appointed as Principal of Western Branch High School and remained in that capacity until his retirement in 2008. Mr. Brandrif's service to Western Branch High earned him the honor of being the longest tenured principal in the state of Virginia. Mr. John R. Sykes III, a Chesapeake native and graduate, was appointed principal in July 2008. Mr. Sykes has received advanced degrees from both Virginia Tech and The George Washington University.

The administration, faculty, and staff at Western Branch High School have remained cognizant of their responsibilities to provide an safe learning environment that encourages personal growth, self-respect, pride in work and achievement, and the appreciation of learning. High standards within our school extend to our community and society. Western Branch High is envisioned as part of a cohesive school community - - one that recognizes the importance of the individual and of the larger society of which each person is a part, that provides for personal enrichment, and that assumes a vital role in education.