WELCOME WEEK
Here, you’ll find out what to expect for the opening of school, from arrivals to Orientation, key contacts, lodging, and more!
until 2025 Convocation
Dear students and families,
Welcome to Cheshire Academy!
We are thrilled you’ve chosen to become part of our lively, warm community, and we can’t wait to welcome you in person when you get to campus this fall. Until then, the information below will help your family prepare and know what to expect for the beginning of the 2025-26 academic year. You’ll find a calendar with key arrival and orientation times; transportation, lodging, and contact information; an FAQ section; and important links.
Please look through this information for the answers to many of the questions you may have. Don’t hesitate to contact one of the staff or faculty members listed with any specific questions not covered here.
I look forward to seeing you on campus!
Go Cats!
Sincerely,
Tom Woelper P’26 | Head of School
Opening of School Guide
This document will provide all details regarding arrivals, schedules, preseason athletes, contact information, international student information, and more!
The arrival calendar below is only for general dates and times. You can find more information in the guide.
Major Dates Calendar
For more information, schedules and arrival times, please see the Opening of School Guide.
September 2025
Tue
2
September 2 @ 5 p.m.
Student Leader, Preseason Athlete, and New International Student Arrival
Optional Arrival: Returning international students may return today or Sept. 6
No arrivals allowed September 3-5, 2025.
Sat
6
September 6 – Welcome Day & Registration
New Student and Returning Boarding Student Arrival
Sun
7
September 7 – First Day on Campus
2025 Convocation
Simosa Field & Track
Mon
8
September 8
First Day of School
Classes and Afternoon Activities Begin, Orientation Continues
Frequently Asked Questions
Please visit the Campus Visits page for more information and a campus map.
- Charged student laptop and phone
- Students will be asked to log in to your student portal account, student email, Orah, and Teams using your devices
- Any final documents (transcripts, academic records) or health records pending
- Payment/financial paperwork/signed contract if pending
- Personal ID for parents/guardians if needed
- For day student drivers: license, insurance ID, and vehicle registration
Please enter the Main Entrance at 10 Main St. and follow the signs for on-campus parking. The best places to park will be in the lots near the Arts Building, Simosa Field, and Field House for close proximity to the Humanities Building, where registration will take place.
For more information on directions, go to our “Visit CA” page.
Once on campus, head to the upper level of the Humanities Building (across from the Arts Building) for registration check-in. Please arrive ONLY during the day/time outlined in the Opening of School Guide. When you arrive at the Humanities building, you will be greeted by both our faculty and student leaders.
No, registration and health forms must be completed before arrival to campus. Students CANNOT come to campus until all paperwork has been completed and submitted. This policy ensures compliance with health, safety, and academic requirements.
Students generally dress casually, though some might choose to dress up a bit for the first day. Please wear what is comfortable for you and we recommended comfortable walking shoes. For students, sneakers are preferred.
According to the portal and the Student and Family Handbook, all clothing should be clean and in good condition with no profanity or inappropriate messaging and full coverage from underarm to mid-thigh. Tops must have straps or sleeves.
Students wear formal dress at Convocation. There will be time to change before the event on Sept. 7.
IDs will be issued on Sept. 6 as part of the check-in process.
Yes! Your family is welcome to help and there will be Student Leaders will be assigned to help you create your home away from home.
Following the designated lunch period on Saturday, Sept. 6, from 12-1 p.m., we will ask families to say their goodbyes before dedicated programming begins. At 1 p.m., a New Families Welcome will take place, and separate student programming will begin. While we understand that these partings can be emotional, we have found that allowing students time to acclimate independently is incredibly beneficial for their personal growth and independence. This space allows them to focus on forming new friendships, meeting their teachers, and getting comfortable in their new environment. We are confident that your children are ready for this new adventure and will thrive in our supportive and caring community.
There will be time to walk around and see where classes are. New students do a walk-through of campus as part of Orientation and then there is also free time.
Parking passes and spots for day students will be taken care of on registration day (Sept 6) — bring license and registration.
School Contact Information
If you have any questions, contact the following faculty or staff member for additional help!
Transportation for International Students
International students may arrange their own transportation to campus during the allowed arrival windows listed in this guide. For students opting to arrange their own transport or for those arriving outside of the scheduled shuttle departure times listed below, some private car services include:
Lodging Information
There are several hotel accommodations within a short driving distance of the Cheshire Academy campus. Some recommendations include:
