The Chesterton Academy of Annapolis is a private, classical high school sponsored by the Society of Gilbert Keith Chesterton, a Catholic organization.  The Society is a canonical private association of the Christian faithful.  The founding of this school started in the Winter of 2018 by a group of parents that have seen the benefits to a truly integrated Classical Education with a Catholic tradition for their children but did not see that option at the high school level. The Chesterton Academy of Annapolis is planning for its first academic year to start in the Fall of 2018.

The unique curriculum model of Chesterton Academy is representative of the curriculum that has been time tested and has worked for St. Thomas Aquinas and Thomas Jefferson. The results will generate students who are complete thinkers.



In the absence of an integrated curriculum in which each discipline informs the other, each part making sense in the light of the whole, the modern academy has literally disintegrated itself into a plethora of fragmented particles, …This world is all one wild divorce court.
– G.K. Chesterton


An education that imparts truth for the whole person–body, mind and soul. Chesterton Academy starts with this end purpose in mind.

Catholic Intellectual Tradition

Each day starts with daily Mass.
Teachers take an oath of fidelity to the Magisterium.


Traditional lecture and Socratic Method.


Faith and Reason meet in every class. Curriculum is integrated in specific time periods.

Forming Tastes

A fine arts program that forms tastes for the good, the beautiful, and the true.


High school is viewed as a time to enjoy a variety of pursuits before locking in and focusing prematurely on a particular education track. The curriculum objective is designed to offer a variety of opportunities that may serve to unlock hidden talents and interests.


Numerous studies show smaller schools help student test scores, teacher satisfaction and student expectation levels and responsibility.

Math and Science

Unlike many other schools, the Chesterton Academy model requires all four years of math and science. The classes are a critical part of the curriculum.