History & Traditions

Brookwood School was founded in 1956 as a non-denominational, coeducational, non-profit day school, born out of the demand for a new independent school following the baby boom of World War II, the explosion of year-round families on the North Shore, and the completion of Route 128.


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.

We are all firmly convinced that we have a wonderful, exciting, stimulating project here, one that we want to keep successful, and one of which we are already proud, and of which we hope to be even prouder as years go by.Brinley Hall, President of the Board of Trustees, speaking to the Parents’ Committee in November 1958

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.



Act of Incorporation and Pip Cutler appointed Headmaster


First opening day

First graduation ceremony

First annual Harold W. Wise Declamation Contest

John Ogden appointed second Headmaster

Completion of the art building and science complex

First Grandparents’ and Special Friends’ Day

A. Marshall (Buck) Lawton appointed third Headmaster

Brookwood entered the computer age when an Apple 2 was purchased

Cutler Activity Center and Beatrice Patton Waters Library opened and Middle School established

Hallaren Computer Lab established

Florence M. Halleran Lower School Wing and Cunningham-Eisemann Gallery dedicated

First Recess Regatta

John C. Peterman appointed fourth Headmaster

First Closing School Meeting to honor graduates

DiCroce Library and Dodge Writing Center dedicated

Lower School expansion completed

Laura Caron appointed fifth Head of School

60th anniversary celebration

Jon Bartlett appointed sixth Head of School



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:

School Meeting (year-round)

A favorite community tradition! Every Thursday morning., the entire school gathers for announcements, student performances, Cultural Enrichment programs and more. Parents and families are invited and encouraged to attend.

Halloween Parade (October)

Students (and faculty!) dress in costumes and parade around the front courtyard. Parents and families are invited and encouraged to attend.

Students in costume during school Halloween Parade

Grandparents’ Tea (November)

Lower School grandparents are invited to join our Head of Lower School for a special reception preceding the Lower School Holiday Play.

Grandparents' tea at Brookwood School

Revels (December)

Students in 4th through 8th grade take part in this heart-warming, joyous performance, along with employee and parent volunteers, on the Friday before winter break begins. Parents and families are invited and encouraged to attend.

Students perform at school event

The 8th Grade Play (March)

An annual musical production that involves the entire 8th grade class and is a must-see for all members of the Brookwood community. Parents and families are invited and encouraged to attend.

Students perform in 8th grade play

Community Art Day (April)

Our campus is transformed into a gallery showcasing the art of the entire student body and live musical performances by students fill the hallways. Parents and families are invited and encouraged to attend.

Teachers and students on Community Art Day

Harold W. Wise Declamation Contest (May)

Named by longtime teacher and administrator Dan Wise for his father who struggled to memorize his lines, finalists in 5th through 8th grade compete in this annual competition of poetry recitation. Parents and families are invited and encouraged to attend.

Grandparents’ and Special Friends’ Day (May)

Grandparents and special friends are invited to experience a morning at Brookwood alongside students, providing an opportunity for generations to connect, reflect and enjoy the gift of time spent together.

Student and older man do crafts during Grandparents' Day

Recess Regatta (May)

In celebration of the art and science of woodworking, 4th grade “sailors” compete to see which boat makes it to the duck house on Cutler Pond first. Students are invited to bring their boats back for a second, third, fourth, or even fifth year following their maiden solo voyage. Parents and families are invited and encouraged to attend.

Group of students participate in Recess Regatta

The Salute (June)

A beloved tradition that honors soon-to-graduate 8th grade students. Every grade participates by singing an original song written for the event as an ode to the graduating class. Parents and families are invited and encouraged to attend.

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