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 @ 7:30
New Student and Returning International Student Arrival
Sun
7
September 7 @ 5 p.m.
2025 Convocation
Simosa Field & Track
Mon
8
September 8
First Day of School
Classes and Afternoon Activities Begin, Orientation Continues
Frequently Asked Questions
Students generally dress casually, though some might choose to dress up a bit for the first day. 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.
IDs will be issued on Sept. 6 as part of the check-in process.
Students wear formal dress at Convocation. There will be time to change before the event on Sept. 7.
Please visit the Campus Visits page for more information and a campus map.
Parking passes and spots for day students will be taken care of on registration day (Sept 6) — bring license and registration.
Registration check-in takes place in the Humanities Building on campus.
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.
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.
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:
