Admission Open House - Oct. 9 [Click Here](https://cheshireacademy.org/events/#REGISTER)
Admission Open House - Oct. 9 [Click Here](https://cheshireacademy.org/events/#REGISTER)
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Reunion Weekend – June 9–10, 2023

Return “home” to where it all began!

June 9–10, 2023


We’ll be celebrating the classes ending in 3 and 8 this year from June 9-10, 2023. All alumni are invited. Pick the events you wish to attend and return home with your Cheshire Academy family, friends, and faculty.


 To register please contact Director of Alumni & Family Relations Kayla Lipsitz ’10
kayla.lipsitz@cheshireacademy.org | 203-439-7276

Reunion 2023 Schedule

Please note, this schedule is subject to change and is continuously updated.


Click here for hotel accommodations


Friday, June 9


5:30-8:30 p.m.

Cheshire Craft Brewing

Wandering Agave food truck

Live music with “Wing It”


Saturday, June 10


9 a.m.

Fun Run


9-11 a.m.

Alumni lacrosse game


10 a.m.-5 p.m.



11 a.m.-noon

State of the school


Noon-1:30 p.m.

BBQ lunch


Noon-1:30 p.m.

50th reunion lunch


1:30-3 p.m.

Alumni basketball game


12:30-4 p.m.

Campus tours


1:30-4 p.m.

Axe throwing & lawn games


2-3 p.m. & 4-5 p.m.

Back to the Classroom

Rick Morris ’73: Environmentalist, conservationist, lover of the sea and all things aquatic 

Write your own memoir with English teacher Allison Bass-Riccio


2-3:30 p.m. 

Archives & Memorial


3:30-4:30 p.m.

Pub trivia


5:15-6 p.m.

Kevin Slaughter Memorial Athletic Hall of Fame & D. Robert Gardiner Arts & Letters induction ceremony


6-6:45 p.m.

Wine tasting with Bill Bishop ’73


6:45-10 p.m.

Dinner & Dancing