Field Day in the spring gives students, faculty, and parents a chance to unwind. Active parents are involved in every aspect of school life. The Wakefield Parents Association is a strong support group and fund raiser for the school. Wakefield supports a diverse program of extra-curricular programs. The school has seven varsity sports teams, teams for lower grades, and a school-wide Winter Sports Week.
Student government is also active and carries significant responsibilities.
Academic competition teams prosper, particularly in Latin and general knowledge categories. Community service is not a requirement but is the choice of many students in the Preparatory School. Faculty members coach students interested in participating in Model UN and Harvard Model Congress.