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.
Current Windward families are invited to join The Windward School for its annual Winter Ice Skating Party at the Winter Village at Bryant Park usually held the last Sunday in January.