Thomas Dale High School has seen several iterations. The school was built in 1906 (right) and named Chester Agricultural High School. Students came from as far away as Suffolk, and in 1907 the school had only two graduates. By 1917, it was renamed Chester High School, and in 1942 it was given its current name, Thomas Dale High School.
In the early 1940s, a new building was constructed on the western side of the original building (above). The structure was later demolished. In 1964, another replacement facility opened less than a mile east on State Route 10.