to 230 Years!

You're Invited: Reunion 2024 May 31-June 1

Return “home” to where it all began! 

Come celebrate an amazing Reunion weekend with your fellow Cheshire Academy Cats. All CA alumni are encouraged to come back, but this year starting with the Class of 2019 (yes, it’s already your five-year reunion!) and earlier milestone classes ending in 4 and 9 are invited to come back and celebrate! 

Milestone year? Just miss campus life and your early days at Cheshire Academy? Any reason is a good reason to connect with old friends and new, as well as some of your favorite faculty members, and relive treasured memories. Grab your friends and come home to CA. 

Read the information and our FAQs below. We can’t wait to see you soon. 

Questions? Looking to connect with classmates or participate in class outreach?  

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


Celebrating a Milestone Year?

2019 (5 years) 

2014 (10 years) 

2009 (15 years) 

2004 (20 years) 

1999 (25 years) 

1994 (30 years) 

1989 (35 years) 

1984 (40 years) 


1979 (45 years) 

1974 (50 years) 

1969 (55 years) 

1964 (60 years) 

1959 (65 years) 

1954 (70 years)  

1949 (75 years) 

1944 (80 years) 


Please note, this schedule is subject to change. Check back for regular updates! 

Friday, May 31, 2024

Welcome Back Gathering Join us at a local brewery and sip on a Cheshire Academy specialty beer: “The CA Wildcat! 

Saturday, June 1, 2024

Among more programming to be announced, check out some Reunion 2024 highlights below. 
  • 50th and Legends Luncheon Hosted by Bob Gardiner
  • Beer Garden & Pub Trivia
  • Campus Tours
  • Win a Game – Get a Prize!
  • The Cats Open, Doubles Tennis & Pickle Ball 
  • State of the School 
  • Hall of Fame
  • Cocktail Hour & Wine Tasting 
  • Campus Tours 
  • Head of School Reception – Don’t miss dinner, dancing, and a special surprise for our community that will surely get you reminiscent of your days at CA!

Interested in joining a fun and casual panel session with your fellow alumni? We are looking for alumni interested in sharing highlights about their professional career paths with CA student leaders. Please email by clicking the button below if interested.

Frequently Asked Questions (FAQ)

Parking is available throughout campus. Please view the campus map for parking locations.  

Yes! The Cheshire Academy store will be open for specific hours during Reunion Weekend. 

Although on-campus housing will not be available, we’ve provided a list of recommended local accommodations (some with discounts) from which to choose. 

Yes, upon registration, you will have the option to choose which events you would like to participate in and make your payment accordingly.  

Of course! We welcome our alumni to invite guests to share in this festive weekend.  

We want you to have the best experience at Reunion! For special accommodations please email kayla.lipsitz@cheshireacademy.org or call 203439-7276. 

If you cannot attend Reunion Weekend due to personal concerns, full refunds will be issued if requested by June 1, 2024. Refunds will be issued after Reunion Weekend. 



Find a place nearby to spend the weekend based on our reccomendations!

Courtyard Marriott Wallingford/New Haven (7.4 mi) Use code “S4132” for a discount  

Holiday Inn (9.7 mi.) 

Cheshire – Southington

CA has blocked a limited amount of rooms to ensure that you can be with or near other reunion attendees, all at a special rate!

Omni Hotel 

(16 mi.)

 Downtown New Haven

The Blake Hotel (17 mi.) 

 Downtown New Haven

Hall of Fame Nomination

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Nominations must be made one at a time. Please submit the form and start a new submission.
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  • Each candidate must have received their diploma or postgraduate certificate from Cheshire Academy.
  • While participating, candidates must have earned outstanding recognition in their sport such as captain, M.V.P., all league, all New England, or All-American at Cheshire and/or at college.
  • Candidates must also have been active in one or more non-athletic endeavors.

Depending on the award, nominators may be required to provide optional information about the nominee, such as letters of support, relevant recognitions, honors, awards or accomplishments, and resumes or CVs. Required or not, letters of support are always welcome. They can be uploaded here or emailed to alumni@cheshireacademy.org.

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Contact information is required should we need to reach out for more information.
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