The Windward School hosts a variety of special events to benefit the School throughout the year. Learn more about them below.
- The Windward Classic Golf & Tennis Outing
- The Windward School Benefit
- Alumni Homecoming
- The Windward School Ice Skating Party
Every other year, The Windward School hosts a spring benefit. The most recent benefit was held on Saturday, March 10, 2018, and honored Drs. Sally & Bennett Shaywitz, Anderson Cooper, and Christine & Stephen Schwarzman. The proceeds from the Benefit go towards impacting the lives of Windward's 862 students.