Dana Hall School was born out of the vision and generosity of Henry F. Durant, who founded Wellesley College and soon discovered that many of his students needed further preparation before entering college. To address this need, Charles P. Dana, a Wellesley businessman, gave Durant a building to use for housing students in a new preparatory school; this served as the first site for Dana Hall School.

Julia and Sarah Eastman, hired from Wellesley College by Henry Durant to run this new school, began classes at Dana Hall School on September 8, 1881. That first year, 18 students paid board and tuition of $325. If they completed the course of study, they were guaranteed admission to Wellesley without further examination. While the Misses Eastman did not neglect the social graces, their "Fitting School" was dedicated to providing women with the type of rigorous mental training that had long been available to men. The founders believed in the equality of women and their right to be educated. Durant and the Eastmans avoided unnecessary rules, stressed individual development and offered a full program of liberal arts education for young women.

The Eastman sisters retired in 1899. The school was then bought by Helen Temple Cooke, whose energy and brilliant mind were dominant forces in the school until her death in 1955. During Miss Cooke's tenure, Tenacre, Dana Junior, Dana Hall, and Pine Manor Junior College were added to form the Dana Hall Schools.

Pine Manor became independent of Dana Hall in 1962, as did Tenacre in 1971. When Pine Manor relocated to Chestnut Hill, Dana Hall moved down Grove Street to the adjoining Pine Manor campus, adding new dormitories, a new dining center and a new gymnasium. The lower grades (seventh and eighth) formed the current Dana Hall Middle School, and the grade nine became a part of the Upper School. The sixth grade was added to the Middle School in 1984.

Dana Hall School's commitment to excellence in education has been reinforced by a succession of exceptional women leaders. Alnah J. Johnston, (1938-1962), Edith B. Phelps (1963-1973), Dr. Patricia A. Wertheimer (1973-1981), and Dr. Barbara S. Powell (1981-1983). Dorothy O. Farmer served as acting head in 1962-1963, as did Ann E. Bekebrede for the academic year 1983-1984. Elaine W. Betts became the eighth headmistress of Dana Hall School in 1984. In 1993, Blair H. Jenkins became the ninth head of school, sharing leadership with Elaine Betts until her retirement in 1995.