About Us
History
In 1901, two elderly sisters realized their dream of founding a school for needy boys. For many years before Charlotte Drinkwater retired as director of the Boston Y.W.C.A., she and her sister, Mary Drinkwater Warren, had welcomed children to their farm in Greenwich, Massachusetts, during the summer months. Their program of farm work, lessons, moral principles, and play became the basis for the early school, and for a curriculum that lasted into the 1980s.
In 1927, aware that Greenwich was part of the area that was to be flooded to form the Quabbin Reservoir, Hillside's Board moved the school to its present location. Throughout the tenures of five headmasters and challenging financial times, the school maintained its self-sufficiency by means of its farm and with the help of its many benefactors.
By the late 1980s, with the farm no longer viable as a support mechanism, it became evident that change was necessary if the school were to survive.
During the 1990s, Hillside increasingly received requests to enroll boys who needed help in closing the gaps in their personal and educational development that were preventing them from realizing their potential. The school's programs are now dedicated to meeting the needs of such students with the same caring commitment as its founders.
