Shadow & Tour at Chesterton
Prospective students are encouraged to spend a full shadow day at CAA.
Visiting students will experience our classes and joyful atmosphere.
Families may also schedule a private tour of the school.
Attend an Open House
Parents and students are invited to attend an Open House.
You will meet our faculty and students and learn about our curriculum.
Open House dates for Fall 2026 will be posted in the summer of 2026.
If you’d like to be added to our admissions mailing list, please let us know by contacting us at: admissions@chestertonannapolis.org
Apply
Our application process is completed online through TADS.
The application for the 2027-28 academic year will be available in mid-October 2026.
The Priority Application deadline for admission in 2027-28 will be announced the summer of 2026.
The application includes a student and family interview with our Headmaster.
An Affordable Education
Tuition & Fees
Chesterton Academy of Annapolis is committed to offering a classical education in the Catholic tradition at an affordable cost to families.
Tuition for the 2026-27 academic year is $12,000 per student.
Families with siblings at the academy receive a tuition discount:
$1500 off tuition for the first sibling
$3500 off tuition for the second sibling
Because tuition does not cover the full cost of education, families are expected to help in fundraising efforts throughout the year.
Financial Aid
Limited tuition assistance is available to families that apply and qualify for aid. CAA utilizes TADS to help allocate our limited aid dollars.
The student application process must be completed in full before being considered for tuition assistance. The deadline for financial aid for 2027-28 is will be in late December 2026 (date to be announced in Summer 2026).
To apply for Financial Aid: https://sssandtadsfa.my.site.com/familyportal
Placement Exam
CAA administers the Classic Learning Test 8 (CLT8) as its placement exam for incoming freshmen.
The test will be administered in November 2026 at Chesterton Academy of Annapolis
RSVP by clicking the button below. If you have any questions, please contact Admissions@ChestertonAnnapolis.org any time.
All students are required to take a placement exam as part of the application and enrollment process. The placement exam is used as a diagnostic tool to ensure students are placed in the appropriate section of math or Latin, and to help identify areas of academic strengths. Latin placement test is offered to students who have previously taken Latin. Email Admissions@ChestertonAnnapolis.org to schedule your Latin placement test.
The test covers the following:
Verbal reasoning skills
Grammar and writing skills
Quantitative reasoning skills
An optional Latin exam is also offered
Admissions Events
