Reunion Weekend – June 10-12, 2022

Return Home to Cheshire Academy

June 10-12, 2022


A combined reunion to celebrate the classes ending in 0, 1, 2, 5, 6, and 7 is scheduled for June 10-12, 2022. Stay in housing on campus or off, pick the events you wish to attend, and return home with your Cheshire Academy family, friends, and faculty for the first time in 3 years.


*While milestone classes ending in 0,1,2,5,6, and 7 will be especially celebrated, all alumni are invited and encouraged to attend Reunion Weekend!


 For all questions, please contact Peter White ’07: peter.white@cheshireacademy.org | 203-439-7276

Welcome Home Reception

Welcome Home Reception

A special “Hard Hat Happy Hour” at Bowden Hall with golf cart tours of the construction of the new multi-purpose field and tennis courts on campus. Friday, June 10, 6-9 p.m.

Register Today

Back to the Classroom

Back to the Classroom

Featuring classes with Mr. Boyd, Mr. Gardiner, Mrs DiGiacamo, and Mr. Ferraro. Saturday, June 11, 1:15-2:45 p.m.

Register Today

Hall of Fame Ceremony

Hall of Fame Ceremony

Kevin Slaughter Memorial Athletic Hall of Fame and Arts & Letters Hall of Fame Ceremony at Slaughter Field. Saturday, June 11, 4-5 p.m.

Register Today

Cheshire Clam Bake & Music

Cheshire Clam Bake & Music

End the day with festive food, drink, and music under the tent on Slaughter Field. Saturday, June 11, 6:30-10 p.m.

Register Today

50th Reunion Brunch

50th Reunion Brunch

Exclusively for alumni of the 50th Reunion classes and family members(1972,1971,1970). Hosted by Head of School Julie Anderson P’19 P’23 at the O’Connor House. Sunday, June 12, 11:30 a.m. - 1 p.m.

Register Today


Friday, June 10


10 a.m.-2 p.m.

Alumni Golf Outing
Farms CC
Contact Peter White to reserve your spot.

6-9 p.m.

Welcome Home Reception
Bowden Hall
Golf cart tours of the construction of the new multi-purpose field and tennis courts will depart every 15 minutes.


Saturday, June 11


9 a.m.

Alumni & Faculty Fun Run
Meet at Gideon Welles Dining Hall
Will conclude at Cheshire Coffee, courtesy of the Office of Advancement.

9 a.m.-7 p.m.

Slaughter Field
Continental breakfast available. 

10-10:45 a.m.

Alumni Affinity Spotlight: Coleman GroupCheshire Academy Library
A special opportunity to honor retired senior master Karen Smith.

11-11:45 a.m.

Cheshire Conversations
Community Forum
Moderated by HOS Julie Anderson.

Noon-2:30 p.m.

Community BBQ, Lawn Games & Beer Garden
Slaughter Field

12:15-1 p.m.

Alumni Athletics Panel
Arthur Sheriff Field House

12:30-2:30 p.m.

Archives Open House
The historic archives of Cheshire Academy will be made available to all alumni and families.

12:15-2:45 p.m.

Back to the Classroom
Community Forum and John J. White ’38 Science Center

1-3 p.m.

Hard hat tours of new field project
Arthur Sheriff Field House

2:15-2:45 p.m.

Alumni Affinity Spotlight: Alumni of Color Mentoring Network
Blue Room, Bowden Hall
An opportunity for alumni who identify as people of color, and are interested in re-engaging with the school as part of the new Alumni of Color Mentoring Network.  

3-4 p.m.

Cheshire Academy Pub Trivia
JJW White Patio
Emcee: Leo Hiertz

4-5 p.m.

Hall of Fame Ceremonies
Bowden Hall patio
Kevin Slaughter Memorial Athletic Hall of Fame and Arts & Letters Hall of Fame Ceremony.  

5:30-6:30 p.m.

Cocktail Reception and Class Photos
Slaughter Field (outside of tent)

6:30-10 p.m.

Clam Bake & Music
Slaughter Field (under the tent)


Sunday, June 12


10:30-11 a.m.

Memorial Service
Bowden Hall

11:30 a.m.-1 p.m.

50th Reunion Brunch
O’Connor House
Exclusively for alumni of the 50h Reunion classes and family members (1970, 1971, 1972)

11:30 a.m.-1 p.m.

All Community Brunch
Gideon Welles Dining Commons



Download a PDF of the schedule.