During the early years of Chester, any child who received formal education traveled to East Liverpool by either ferry or a smaller boat. Attendance at that time was often hazardous and uncertain. The first attempted school was a one room log house located at Fairview Road. Cylis Mercer was the first teacher. The second school was located on the Riley farm, also located in the Fairview Road vicinity.

The third school building was located on Cunningham Run, just east of First Street near the Rhodes Service Station. J.J. Cunningham was the first teacher in this school building, which also housed the post office and a general store. It was called the Mechanics Lodge. Classes were attended here throughout the 1890's until 1903.

In 1900, the Central School was built along the north side of Indiana Avenue between Third and Fourth Streets. Before 1903, the classes were not graded. During 1903, the classes were graded and later in that year, a four year high school was implimented with freshmen and sophomore classes formed. This school was a two story frame structure with a steeple.

In 1904 Chester was organized as an independent school system. The original board of education were: Thomas WARD, Peter NOFCIER, and Thomas L. YOUNG.

In 1906, the brick Central School was constructed at Third and Indiana. The first and only graduate that year was Olive Hamilton.

In 1908, the Sacred Heart School was officially opened on Sept. 19th. Miss Elizabeth McKenna was the first teacher for this school, and enrollment that year was 65 students.

In 1907, the Washington School was built, and in 1925 Chester High School was constructed at the corner of Fifth and Indiana. This school is still in use today as Oak Glen Middle School and houses students in grades 7 and 8.