Welcome Windward Alumni!

The Windward School Alumni Program works to provide value to alumni through:

  • Networking opportunities
  • Panel/lecture speaking opportunities
  • Mentor opportunities
  • Homecomings/reunions
  • Other events such as senior night and the Windward Fund alumni fundraiser
  • Keeping up with our alumni and highlighting our successful alumni

Please stay tuned for upcoming alumni events and contact us if there’s anything we can assist you with.

Please note: the Alumni Office uses the year of high school graduation as a student’s Windward class year.

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Alumni News

Alumni RoundTable

The Windward School Alumni Office held its first ever Alumni Roundtable on October 27, 2020.  James D’Amato ’06 and Tess Tregellas ’14, shared their experiences as writers, actors, and producers, and how dyslexia has shaped their similar, yet unique paths.


If you missed the event, you can watch the recording here and hear how Windward inspired them to be their best selves!

The Windward School College Planning Seminar - November 18, 2020

The Windward School Alumni Office welcomed back Carolyn Mulligan from Insider Network to College to host the College Planning Seminar. This special event was exclusive to Windward alumni in grades 10 and 11 and their parents/guardians. Carolyn Mulligan, College Consultant and Owner of Insiders Network to College, shared her expert knowledge on how to transform the college search and application process from a complicated maze to an expertly-guided journey with specialized knowledge in learning disabilities and ADD/ADHD.

Questions? Reach out to alumni@thewindwardschool.org