One broad goal of the program is to introduce students to the need for and the value of noble and generous actions, as well as the joy and privilege of giving service to people who need help. Learning through being involved in the community and caring for the environment are every bit as essential as preparation and success in academic subjects. Students are encouraged to engage in hands-on service projects through which they learn they can make a difference in their community.
Students have access to a wide range of activities outside of the classroom.
Student Council meets regularly to promote school spirit, plan special events, and help in nearly every aspect of school life. A Human Development program in both the Middle and Upper Schools is designed to present a number of issues that are relevant to adolescent growth and development. Windward is justifiably proud of the school's Performing Arts Department and theater productions, most notably the fall play and the spring musical. Students may audition for these productions and may also participate behind the scenes as stage manager, house manager, set crew member, artist or publicity manager. The school also offers the opportunity to participate in The International Thespian Society, The Madrigal Singers, Jazz Ensemble, Chamber Players, Yearbook production and the school newspaper.