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As many small towns do today, Deerfield, Massachusetts, struggled with how to fund a free, public high school from as early as the mid-1800s. In 1858, under state pressure, Deerfield Academy opened a free high school that was co-funded by the town. In 1875, a Deerfield widow, Esther (Harding) Dickinson, left a substantial fortune for a separate free high school. The money was combined with funds from Deerfield Academy for one new building, and the "Deerfield Academy and Dickinson High School" opened in 1878. Deerfield students could go to the high school for free, but had to pass the entry test as did paying students. Students who were not from Deerfield paid tuition (which varied by term and department, in this 1888 prospectus). Until 1917, instruction was shared, with only the source of funding differentiating students from each other. Although the two schools were combined, the institution was still quite small -- in 1900 the student body consisted of only eleven students of both sexes.

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