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.
Arrival Overview Calendar
For more information, schedules and arrival times, please see the Opening of School Guide.
August 2025
Fri
23
August 23 @ 5 p.m.
Student Leaders Arrival
Student leaders to arrive and check in on campus. Training schedule to come.
Mon
26
August 26 @ 9-11:30 a.m.
Preseason Athlete Arrival
Specific athletic schedule and programming to come.
August 26 @ 9-5 p.m.
New International Student Arrival
Please see Opening of School Guide for specific information.
No arrivals allowed August 27-30
Sat
31
August 31 @ 9 a.m.-12 p.m.
New Boarding Student Arrival
August 31 @ 12-1 p.m.
New Day Student Arrival
September 2025
Sun
1
September 1 @ 5 p.m.
2024 Convocation
Simosa Field & Track
Mon
2
September 2
First Day of School
Half Day of Classes
September 2
Orientation and Community Programming
including Field Day
Tue
3
September 3
Half Day of Classes
September 3
Orientation and Community Programming
including block party (ice cream, lawn games and more)
Wed
4
September 4
Half Day of Classes
September 4
Orientation and Community Programming
Thu
5
September 5
Regular Class Schedule
Friday
6
September 6
Regular Class Schedule
Formal Friday, Community Dinner, Community Weekend
Sat-Sun
7-8
September 7-8
Welcome Home All Community Weekend
Designed to set the tone for the 2024-2025 school year by fostering a sense of belonging, connection, and acceptance within our diverse school community. Mandatory programming on Friday and Saturday.
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:
For international students with a Standard or Reduced fee package, please see the Opening of School Guide for more information on shuttle times, locations, and guidelines.
Lodging Information
There are several hotel accommodations within a short driving distance of the Cheshire Academy campus. Some recommendations include:
