Lebanese-born poet Kahlil Gibran, an "intimate friend" of headmistress Mary Haskell, designed a ring for her students depicting a "flower" "growing" in an open "hand".

In 1939, the school implemented a form of community self-governance modeled after the traditional New England town meeting.

The goal of the Module, or "Mod" System, is to provide a framework to allow students to focus on fewer subjects more intensively during a given term.

The Cambridge School of Weston offers the following interscholastic sports: Soccer, Cross country running, Field hockey, Basketball, Baseball, Ultimate, Volleyball, Tennis, and Girls' lacrosse.

[6] Additional fitness courses offered include: Yoga, Rock climbing, Fencing, Bicycling, Weight training, Golf, Table tennis, Dance, and Martial arts.