There’s nothing like coming back to campus to relive memories, catch up with friends, and see what’s new. Alumni events are a fun, meaningful way to reconnect with classmates, favorite teachers, and the community that will always feel like home. We hope you'll join us for one—or many—of the events happening this year!
Reunion
We love welcoming alumni back to campus each year for Reunion—a cherished tradition that brings our community together to reminisce, reconnect, and celebrate lasting bonds. It’s a time to catch up with classmates and faculty and revisit the spaces and places that shaped so many memories. Save the dates for Reunion Weekend 2026 (May 29-31). Details coming soon!
Reunion 2025 PhotosAlumni Events
Mark your calendar for our annual events, and be sure to check back or follow Brewster’s social media accounts for updates on regional and special gatherings throughout the year.
Reach out with any questions to alumni@brewsteracademy.org.
Reception in Williston, VT
Get ready for a great night in Williston, Vermont! Join us on Friday, January 16, from 5:30 to 7:30 p.m. at Rise to the Top for a special Brewster Academy reception for alumni, current families, and prospective families. We’re excited for an evening of connection, conversation, and community.
Learn More and Register
EYBL Post-Game Reception
Join us for a special post-game gathering that brings the Brewster community together. Alumni, prospective families, and friends are invited to connect with Brewster’s EYBL National Team players and families following a big game in Springfield, Mass.
Learn More and Register
The Winni Classic
Join us for a day of sticks, pucks, and fun! We’re excited to welcome alumni, families, and friends for a great time on the ice. Reconnect with faculty, classmates, and fellow Bobcats.
Register Here
Maine Mariners Hockey
Alumni and their families are invited to join us for the Maine Mariners vs. Greensboro Gargoyles on Sunday, March 29th at 3 p.m. at the Cross Insurance Arena in Portland, Maine!
Register Here
Boston Networking Event
Save the date for the Northern New England Peer Schools networking reception at Hampshire House on Tuesday, March 31, 2026. Registration coming soon.
NYC Networking Event
Save the date for the Northern New England Peer Schools networking reception at The Penn Club (30 W 44th Street, New York, NY) on Thursday, April 2, 2026. Registration coming soon.
Reunion 2026 Save the Date!
May 29-May 31, 2026. Be sure to mark your calendar for the last week in May to return to Wolfeboro and reconnect with the Brewster community.
