Get information on Commencement and other year-end events [Click Here](https://cheshireacademy.org/commencement/)
Get information on Commencement and other year-end events [Click Here](https://cheshireacademy.org/commencement/)
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Updates & Resources


Parents, guardians, and students – this is where you will find all kinds of helpful information and school resources related to Cheshire Academy. Whether this is your first year or your fourth, if you are newly enrolled or a returning family, a day or boarding student, from the U.S. or abroad… almost everything you need is here. 


This page is updated throughout the year, so bookmark it and check in periodically. If you have questions or need more information, please refer to the list of contacts at the bottom of the page for departments and CA faculty and staff who can assist you.


NEW and re-enrolling students and families – For 2023-2024, be sure to follow the Enrollment Checklists for: Boarding and for Day enrollment.


Also, be sure to always refer to the My Cheshire portal, where you can log in with your username and password to access your personal CA information and additional resources from all departments. Here’s an example of what you will find on the My Cheshire Parents Resource Board, after logging in:



The End of Year Events schedule, for students – and for families – can be found here. For more information on Commencement, please visit our Commencement page.

(as of May 9, 2023)




Academic Office 
Rachel Wright, assistant head of school for academic affairs, can answer questions related to academic life and course selection. 


Young Kwon, dean of academic affairs, can answer questions related to course selections.
Sharyn Iadarola, academic office manager, can address questions about textbooks, summer reading, and anything else you aren’t sure who to ask. Please call the Academic Office at 203-439-7240. 
Elisa Laudati, director of the Roxbury Academic Support Program and Educational Services, can answer questions about enrolling in the Roxbury program for one-on-one academic support, or about learning accommodation plans and educational testing. 
Athletic Department 
Jim McCarthy, director of athletics, can answer questions about afternoon activities. If you are interested in joining a fall sport at the varsity level and would like to come to preseason, contact Mr. McCarthy to be put in touch with the head coach. 
Community Life Office 
Mark Kolman, dean of students, can answer questions related to the Student & Family Handbook, the student experience for boarding and day students, community programming, discipline, and attendance. 


Mark Cheong, director of residential life, can answer questions related to the boarding student experience. 

Health Center 
Debra Bond, director of the Richmond Health Center and pediatric nurse practitioner (APRN), is available to field any questions relating to Magnus Health, medication concerns, or health records. You may also call the Health Center at 203-439-7280. 
Technology Office 
If you are having trouble accessing the My Cheshire portal, your CA email, or anything else related to Cheshire Academy technology, email our technology help desk with the details of your issue. 


Plan ahead for your arrival and vacations using the 2023-2024 school calendar (Released March 10, 2023)


The 2022-2023 school calendar.  


View and save the daily academic schedule for 2022-2023. 


The End of Year Events schedule can be found here.

(as of May 9, 2023)


MY CHESHIRE PORTAL - Login for More Resources & Information

While the Cheshire Academy website features general content about our school, programs, and community, additional important information for enrolled students and families is accessed through the password-protected My Cheshire portal.


Parents of newly enrolled students are sent their My Cheshire parent portal account creation emails usually within 1-2 business days of completing the enrollment process, the contract, and deposit. (Log in instructions for new parents.)


Newly enrolled students will be sent their CA email and portal account info in or around July 14. 


Through the portal, families are able to: 

    • Complete their Magnus Health registration and submit forms (by July 14) 
    • Review and sign the 2022-2023 Student & Family Handbook
    • Review and update demographic and contact information
    • Provide emergency contact information 
    • Review the dress code 
    • Access their requested courses and required textbook information 
    • Sign up for athletics, music ensembles, theater, and other activities  
    • Complete a roommate compatibility form (boarding students)  
    • Access a list of recommended dorm room supplies (boarding students) 
    • Access device specifications for student technology  

ORIENTATION PROGRAMS 2023 - for students new to Cheshire Academy - TBA

August and September 2023 Orientation program information will be announced in the spring.


If you’re interested in seeing last year’s 2022 orientation schedule, click here.



Once plans are set for the start of the new school year, 2023-2024, students, parents, and families will receive a complete guide to the activities, events, and expectations for opening days.

Simply for your information – if interested in seeing what took place last year (2022), review the Opening of School 2022 Guide to see detailed information about expected arrival windows, transportation and lodging information for students and families traveling to campus, and how they spend their first days of the new school year. This is last year’s guide, for reference only.  



The health registration process for 2023-2024 for new and returning students will open in the spring. It is completed through the Magnus Health online service and is due by July 14.  


For families new to CA, more details can be found here (PDF) in a letter from the Health Center.


Parents/guardians who have any technical questions when accessing Magnus Health, completing the forms, or registering online, please contact Magnus Health directly at service@magnushealthportal.com or by calling 877-461-6831.


If you have any specific medical questions or wish to discuss confidentially any medical concerns regarding your child, please contact the Cheshire Academy Health Center Team via email at nurses@cheshireacademy.org or by calling 203-439-7280.


New students, along with their parents and guardians, will be emailed a link to register for course selection meetings. This begins a dialogue which results in a student’s final course selection after all required courses and elective options are discussed. 


In the meantime, please review the graduation requirements and course descriptions in our 2023-2024 Curriculum Guide and make note of any questions that you might have. 



Families are responsible for purchasing textbooks independently and may purchase them from any supplier.


Summer reading and required textbook information will be made available on the My Cheshire portal.