WELCOME WEEK
Here, you’ll find out what to expect for the opening of school, from arrivals to Orientation, Convocation, key contacts, and more!
until Convocation
Dear students and families,
Welcome to Cheshire Academy!
We are thrilled you have chosen to become part of our community, and we can’t wait to welcome you in person on campus this fall. We’re busy preparing for Opening of School, August 31-September 7, a week of preseason athletic sessions, Orientation activities, and more, to help you settle into the 2026-27 academic year.
Your journey starts here. Treat this page as your guide to a smooth start to what promises to be a meaningful school year at Cheshire Academy.
Questions? Don’t hesitate to reach out via the Key Contacts list below.
I look forward to seeing you on campus!
Go Cats!
Tom Woelper P’26 | Head of School
Opening of School Guide
This document will provide details regarding arrivals, preseason information, 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.
School Store Hours
The School Store (located on the lower level of the Student Center) will be open during the following dates/times:
- Sept. 4 – 12–3:30 p.m.
- Sept. 6 – 9 a.m.–12 p.m.
Key Opening Dates
For more information, schedules and arrival times, please see the Opening of School Guide.
August
Mon
31
9-11 a.m. Arrival Window
Student Leader, Invited Preseason Athlete Arrival
- 10:30-11:30 a.m. – Drop-in Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 6-8 p.m. – S’mores & More New Family Event
No arrivals allowed September 1-3, 2026.
September
Fri
4
Welcome Week Begins
New Boarding Students Arrive
9 a.m.–3 p.m. Arrival Window
- 10-11 a.m. – Drop-In Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 2-3 p.m. – Drop-In Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 3:30–5 p.m. — Head of School Welcome/Faculty Panel for New Boarding Students & Families
- 5:15–6:45 p.m. — Boarding Student Family Social, The Reading Room, Cheshire
*Note: Parents & students say farewells during welcome panel as student programming begins at 4 p.m.
Sun
6
New Student Orientation
New Day Students Arrive
9 a.m.–12 p.m. Arrival Window
- 10:30-11:30 a.m. – Drop-in Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 12-12:10 p.m. – Parents & families say farewell; students required at 12 p.m. lunch
- 12:15-1:30 p.m. — Head of School Welcome & Faculty Panel for New Day Parents
- 1:45-3 p.m. — Day Student Family Social
- 8 p.m. — Required programming for ALL NEW STUDENTS until 8 p.m.*
*Day students may be picked up between 8-9 p.m.
Mon
7
REQUIRED FOR ALL STUDENTS
9 a.m.-12 p.m. – Returning Boarders Arrival Window
1-3 p.m. – Returning Day Students Arrival Window
Convocation
- 10-11 a.m. – Drop-In Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 2-3 p.m. – Drop-In Office Hour w/Head of School Tom Woelper P’26, Hasel Room Library 111
- 3:15-4:15 p.m. – CAPFA Meet & Greet Drop-In
- 5-6 p.m. – Convocation Ceremony, followed by Student/Faculty Dinner
- Arrive by 4:30 p.m. in formal dress
- 6:15-7:15 p.m. – Head of School Reception for Parents & Guardians at O’Connor House patio
- Day students picked up by 7:15–7:30 p.m. when dinner concludes
Tue
8
Classes, Afternoon Activities Begin
First Day of School
Regular schedule
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. Students who arrive without completed documents will need to find other accommodations until forms are finalized.
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 Induction & Convocation. Patches will be handed out at the New Student Induction Ceremony, and ties may be purchased at the school store.
IDs will be issued as part of the check-in process.
Yes! Your family is welcome to help and there will be Student Leaders assigned to each dorm for assistance.
We will ask families to say their goodbyes and send off students once Orientation begins. 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 — bring a current valid license, registration, and insurance.
Key Contacts
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:
