Hampton High School is the direct descendent of the Syms-Eaton School, the first free school in America established in the American colonies. Syms Free School was founded in 1647 and soon after, in 1659 the Thomas Eaton Charity School was begun. These two schools operated individually until 1803 when the schools were combined and moved to Hampton. They opened in 1805 as one school.

In 1845 Hampton Academy was formed from the joint school but was later claimed by the school commissioners who made it the "district school" in 1855. Boys were taught in one half of the building and girls in the other. The school was burned during the Civil War and the burning of Hampton in 1862. After the war, the original mortgage bonds were reinvested and the second Hampton Academy was constructed on the same site as the original. It included the first high school building which opened in 1875. High school classes were introduced between 1887-1890. Hampton High School had its first commencement in 1896 with the graduation of two students, Miss Bessie Birdsall and Miss Blance Bullifant.