Philip "Pip" Cutler, a faculty member at St. George's School, along with Dr. Francis Caswell and Brinley Hall, set in motion negotiations to purchase Villa Crest stables on Brookwood Road in the spring of 1956.

By December, the school was incorporated as The Essex Country Day School and in January 1957 the name was officially changed to Brookwood School. Renovations to the building and grounds commenced in the spring and summer, and in September 1957 the Board of Trustees approved the budget and Founding Headmaster Cutler reported the first enrollment of 64 students: 16 Nursery, 20 PreK, 17 Kindergarten and 11 1st grade.



In the early days, registration took place under a maple tree where Headmaster Cutler sat at a folding table with pen in hand while parents stood in line to give him names of their children. Though Headmaster Cutler retired in 1973, the values he stood for remain.

John Ogden served as Headmaster until 1979, A. Marshall Lawton from 1980 through 1992, John Peterman from 1992 through 2015, and Laura Caron from 2015 through 2021. Jon Bartlett became Brookwood's sixth Head of School in July 2021.





A variety of annual school-wide traditions provide students and families with opportunities to connect with one another while celebrating our rich history and values that endure. Noteworthy events include: