Divisions

Laying the foundation for academic and personal growth.

Middle School marks the beginning of each student’s Windward experience—a time to explore new ideas, build academic and social-emotional foundations, and become part of a community that values integrity, curiosity, and individuality. With vibrant classrooms and a deeply supportive faculty, Middle School students learn to ask questions, advocate for themselves, and take meaningful risks.

Throughout these years, learning goes far beyond the classroom:

Building independence, identity, and intellectual curiosity.

The Prep Division welcomes students into Upper School, guiding them as they become more independent, self-aware, and academically engaged. The curriculum becomes more rigorous and personalized, friendships deepen, and students begin taking on leadership and service roles across campus life.

College Counseling begins here with age-appropriate, exploratory programming. Students are encouraged to explore their passions, develop their talents, and begin thinking about how their interests can shape future opportunities. They attend information sessions, learn about the college search process, and are invited to reflect on their developing identities—not just in preparation for college, but for life beyond Windward.

Grade-specific retreats help students reflect, connect, and lead with purpose:

Preparing for college, leadership, and life beyond Windward.

In the Collegiate Division, students engage deeply in advanced academics, take electives that reflect their evolving interests, and assume leadership roles in clubs, sports, the arts, and student life.

College Counseling continues with individualized support, encouraging students to take ownership of their college search while keeping balance and purpose at the center. The focus is on finding the right fit—colleges that align with each student’s goals, values, and potential—not rankings.

Key experiences shape this final stage: