Homecoming & Reunion Weekend

Join us October 4th-6th, 2019

Mark your calendars, Trinity-Pawling community! Homecoming and Reunion Weekend 2019 will be held on campus from Friday, October 4th through Sunday, October 6th. Highlights include Homecoming games, Athletic Hall of Fame Induction, Reunion dinners, and more. Stay tuned for registration information. We hope to see you!

Are you in a Reunion Class this year? Graduation years ending in 4's and 9's...that means you! Visit the Reunion Classes for details about your reunion chairs, accommodations, classmates planning to attend, and more.

Weekend Schedule

*Please note: This schedule is subject to change. 

Friday, October 4, 2019

School Store Hours:  8:15–11:30 AM and 12:30–5:00 PM

9:30 AM - 1:30 PM   Sporting Clays  Ten Mile River Preserve  (Pre-registration required)

11:00 AM   All-School Chapel Service  All Saints’ Chapel

11:45 AM   Family Style Lunch  Scully Hall (Pre-registration required)

1:00 PM     Campus Tours with Alumni Ambassadors  Cluett Lobby
Is your son interested in joining the Pride?  Admissions interviews available by appointment only.

1:30 - 3:30 PM   Fly-fishing  Trinity-Pawling School Pond  (Pre-registration required)

2:00 PM     Open Classes  Dann Academic Building

3:00 PM     Registration and Welcome Center open  Cluett Lobby
Pick up your Trinity-Pawling swag!

4:00 PM     Shuttle from Danbury hotels to campus

5:15 - 6:00 PM     Leadership Donor Reception  Gamage Gardens
Meet with the Headmaster and new Board President Erik Olstein ’86, P’11, ’14, ’17.

6:00 - 9:30 PM     Welcome Dinner, Cocktails, and Distinguished Alumni Awards  Scully Hall
Your class photo will be taken at this event!  Jacket and tie optional.

Saturday, October 5, 2019

School Store Hours:  9:00–12:15 PM and 1:15–5:00 PM

8:00–9:30 AM    Warm breakfast buffet available  Scully Hall

8:30 AM     Shuttle from Danbury hotels to campus

8:30 AM–2:00 PM    Registration and Welcome Center open  Cluett Lobby
Pick up your Trinity-Pawling swag!

9:30–10:15 AM    Meet Today’s Student Leaders  Gardiner Library and Learning Commons
Moderated by Headmaster Taylor

10:30–11:15 AM   Special Programming with Steve Hannock ’69 and Ned Reade  Gardiner Theater

11:15 AM    Sing with the Choir!
Join the Choir for the Alumni Memorial Service. Please arrive promptly for practice. All Saints Chapel

11:30 AM    Alumni Memorial Service  All Saints’ Chapel
12:30–1:30 PM   Buffet Lunch  Smith Field House

1:30 PM   Dedication of Class of 1964 Alumni Room  Smith Field House

1:45 PM   Athletic Hall of Fame Induction  Smith Field House, 1964 Alumni Room
Join us as we celebrate Sean Casey ’89, Foster Orton ’64, Bill Shannon ’69, and Peter Wyeth ’64.

3:00 PM   Appalachian Trail Tour  Meet in Cluett Lobby

3:00 PM  Varsity Soccer vs. Berkshire
3:00 PM  JV Soccer vs. Berkshire
3:00 PM  Third Soccer vs. Berkshire
3:00 PM  Cross-Country at Berkshire
4:00 PM  Homecoming Football Game vs. Taft  Coratti Field

*Please be aware
:  According to the NEPSAC Code of Ethics and Conduct, the use of Alcohol and illegal drugs should not be associated with any athletic event on campus.

Cocktails and Hors D’oeuvres immediately after the football game  Field House Terrace

Following cocktails:  Southwestern Celebration  Smith Field House
Your class photo will be taken at this event!  Jacket and tie optional.

Class of 1969 – 50th Reunion Dinner  Gamage House
Class of 1964 – Dinner and Dedication of 1964 Alumni Room Smith Field House   

9:00 & 10:00 PM   Shuttle from campus to Danbury hotels

Sunday, October 6, 2019

10:00 AM–12:30 PM    Brunch available  Scully Hall

Monday, October 7, 2019

10:00 AM  15th Annual Trinity-Pawling Golf Outing  Southward Ho Country Club, Bay Shore, NY

Accommodations / Lodging


Hilton Garden Inn
119 Mill Plain Road
Danbury, CT 06811
Room Blocks w/ Discounted Pricing - $119 per room

Hotel Zero Degrees
15 Milestone Rd
Danbury, CT 06811
Single King - $149 // Double - $169

Transportation to Campus


A shuttle schedule will be available once registration has opened in the coming months.

Members from the Class of 1984 on Coratti Field during Homecoming and Reunion Weekend
Members from the Class of 1979 during Homecoming and Reunion Weekend at Trinity-Pawling

Every time I stop in for Homecoming and Reunion Weekend, I realize I need to come back more often. It's so great to see everyone!

Brian Desrosier ’76

Reunion Classes

Class of 1964 - 55th reunion

Class of 1969 - It's your 50th reunion!

Class of 1974 - 45th reunion

Class of 1979 - 40th reunion

Class of 1984 - 35th reunion

Class of 1989 - 30th reunion

Class of 1994 - It's your 25th reunion!

Class of 1999 - 20th reunion

Class of 2004 - 15th reunion

Class of 2009 - 10th reunion

Class of 2014 - 5th reunion

If you would like to serve as a Reunion Chair or on a committee, please email alumni@trinitypawling.org