In 1951, after Max Bondy's death, his son Heinz succeeded him as headmaster.[7] Heinz Bondy led the school for 25 years until it closed in 1975.[8]
Operated according to progressive education principles, the school was unusually democratic in its governance, with a student government that was empowered to make all nonacademic rules. As of 1970, there was no dress code, student publications were not censored, and there were no restrictions on student political activities. The school's philosophy held that the exercise of freedom would help students become responsible, self-directing people.[7]
As of 1970, Windsor Mountain had about 250 students, including about 40 African Americans.[7]
Educator Hans Maeder, who was later to establish and lead the Stockbridge School, taught at Windsor Mountain School for a year in the 1940s. Poet Gerald Hausman taught at Windsor Mountain School from 1969 to 1976.[12]
Eric "Rick" Goeld, who attended Windsor Mountain from 1961 to 1963, recently published "People of Windsor Mountain," which is a history of the school spanning the years 1920 to 1975. The book includes many remembrances and personal stories of alumni and former faculty.
There is also another recently published book By Roselle Kline Chartock, a retired professor of education from nearby Great Barrington, titled Windsor Mountain School A Beloved Berkshire Institution. This book is centered on Windsor, referencing several other private schools of the era in the Berkshires, which focused on progressive education.