Upcoming Events

A blue and gold Trinity-Pawling banner hangs on Cluett

Celebrate with us!

Mark your calendars, Trinity-Pawling community — these are events you don't want to miss!

December 8, 2025
New York City Holiday Reception

6:00-8:00 PM
Union Club of the City of New York
101 East 69th Street, New York, NY 
Graciously hosted by Jean Doyen de Montaillou and Michael Kovner ’58

RSVP TODAY VIEW ATTENDEES

December 11, 2025
Boston Holiday Reception

6:00-8:00 PM
Harvard Club of Boston
374 Commonwealth Avenue, Boston, MA
Graciously hosted by Phil Haughey ’53

RSVP TODAY VIEW ATTENDEES

December 14, 2025
Candlelight Service and Reception

5:00 PM
All Saints' Chapel, Trinity-Pawling School 
Hosted by Head of School Bill Taylor and Jennifer Taylor 

RSVP TODAY VIEW ATTENDEES

March 24, 2026
Palm Beach Reception

Palm Beach, FL
Hosted by Dick Bauer ’70

More details and registration coming soon! 

June 4, 2026
Washington, D.C. Reception

University Club
1135 16th St. NW, Washington, D.C.
Graciously hosted by Kathy and Erik K. Olstein ’86, P’11,’14,’17; Ryan E. Olstein '11; Kathryn and Kenneth B. Weeman, Jr. '59, P'92, GP'27; and Carter A. Weeman '92

More details and registration coming soon! 

June 15, 2026
Cape Cod Reception and Golf Outing

Cape Cod, MA
Reception hosted by Becca and Tom Ahrensfeld ’73, and Chris Roux ’73
Golf Outing hosted by Tom Ahrensfeld ’73, Kevin McGrath ’73, Chris Roux ’73, and Will Stephens ’73

More details and registration coming soon! 

Relive the Moments!

View photos from past events.

CLICK TO VIEW PHOTOS

Logo for the Pride Perspectives webinar series

RECENT WEBINARS

Pride Perspectives is a series of webinars featuring key members of the Trinity-Pawling School community. Join hosts Head of School Bill Taylor and Director of Admission Jeff Beck, along with Trinity-Pawling faculty, as the Pride Perspectives series continues throughout the year!

VIEW ALL WEBINARS

A group of Trinity-Pawling alumni smiling in front of a Christmas tree during the New York City Holiday Reception
A group of Trinity-Pawling alumni and friends during a football game on Coratti Field
A group of Trinity-Pawling alumni on a golf course during a recent golf outing

If you have any questions about upcoming Trinity-Pawling events, please reach out to Chris Wilson at cwilson@trinitypawling.org.
For questions related to Homecoming and Reunion Weekend, please email alumni@trinitypawling.org or call 845-855-4823.
To receive details about our forthcoming events, please submit your updated contact information to ensure you're on our mailing list.

All events are subject to change.