Whether you graduated from our High School or attended Oakwood for only a few years, you are important to us and will always be considered part of the Oakwood Alumni community!

Oakwood Alumni provide a vital link to our school’s history and are a reminder of our dedication to educating the whole child and creating a love of learning in each student. We hope that you will take one of these opportunities to get involved at Oakwood and to demonstrate your connection to our school:

  • Join us for Oakwood's inaugural Homecoming celebration on Saturday, January 8, 2022!
  • Come back to Oakwood for a visit in your favorite classroom or be part of an Alumni panel to talk about your experience at Oakwood School and after.
  • Volunteer to help the Alumni Office locate your classmates or organize a class or regional reunion of Oakwood Alumni.
  • Donate items, attend, or volunteer for our annual Auction or attend one of our annual events like the Fund Run, musical or drama performances, or graduation.

Your continued participation in the life of our school is important to our current students and sets an example for future alumni to join in Oakwood’s legacy. Please contact us at alumni@oakwoodway.org to update your contact information or submit an update for the Alumni Spotlight section of our website and annual Book of Gratitude.

We look forward to hearing from you and seeing you around Oakwood soon!

Homecoming 2022

Join us on campus for the many exciting events during Oakwood's inaugural Homecoming event where you can reconnect with classmates, friends, faculty, watch or participate in Alumni athletics games, watch an Alumni theatre performance, and tour our beautiful expanded campus, while ending the day with an on-campus reception! 

Please reach out to alumni@oakwoodway.org if you would like to help plan alumni get togethers for Homecoming weekend! We look forward to seeing you soon!

Alumni Homecoming 2022


20th Anniversary Alumni Reunion Celebration
20th Anniversary Alumni Reunion Celebration

On Saturday, May 18, Oakwood Alumni and their parents from the classes of 2009 through 2018 celebrated with a 20th Anniversary Reunion Celebration. Thanks to Nasreen Ahmed, P '13, '15, the gym was beautifully transformed for our guests to enjoy.

Current and former faculty and staff loved reminiscing with our alumni and sharing favorite memories of their time at Oakwood. Head of School Michelle Helvey led tours of the new Liberal Arts Building and Upper School Gymnasium, which are part of our Campus Expansion Project, in conjunction with our Spreading Our Roots campaign. Guests marveled at the sheer size of the spaces, as well as the opportunities that these new additions will offer current and future students. Alumni and their parents were also treated to a wonderful performance by our High School Vocal Ensemble throughout the evening.

Remarks were made by Ted and Michelle Helvey, and Patty Crone, with Madame de Bree closing out the evening with a toast to our alumni with special sentiment toward our first graduating class' 10th reunion--the class of 2009!

We always love to hear what our alumni are up to after their time at Oakwood and look forward to many more visits with each and every one of you! Thank you to all who were able to join us Saturday evening.


Alumni Liaison

Sheryl de Bree

(408) 782-7177 x133
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Alumni Share Their Thoughts About Oakwood

Our alumni have much to say about their Oakwood experience, and we interviewed some of them to get their perspectives. Watch what they have to say in the following videos:


We love to hear from alumni and parents of alumni on the where abouts of any of our former students. Please share news and major life milestones with us, as well as current contact information by completing our Alumni Update Form.