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Chesterton Academy of St. Mary's - Southern Maryland

High School with a Higher Purpose

 

MISSION. The mission of Chesterton Academy of St. Mary’s is to raise up a generation of joyful leaders and saints, educated in the Classical tradition and the truths of the Catholic faith, abounding in the skills and character requisite for success in college and professional life as well as in building up the kingdom of God, and to excel in service of family, of country, and of Christ our Lord. We seek, ultimately, to prepare our students to triumph over materialism and to accept our Lord's offer to have life and have it abundantly. 


The Chesterton Academy of St. Mary’s is a classical high school in the Catholic tradition located in St Mary’s County, Maryland. We are sponsored by the Chesterton Schools Network, a network of over 70 Schools and growing in the US, Canada, and Europe.

We were founded by a group of families and educators in Southern Maryland who wish to provide students with a rigorous classical education rooted in the Catholic faith.

The school follows the Socratic method of teaching, with a focus on Classical Literature, Philosophy, Science, Mathematics, History, and Latin. The Chesterton Academy of St Mary’s is joyfully Catholic.

Students grow in faith through attendance at daily Mass, annual spiritual retreats, courses infused with Catholic teaching, and a staff in love with Jesus and who are asked to take an oath of fidelity to the Magisterium of the Catholic Church. 

 

Explore Chesterton

Humanities

Fine Arts

Math and science

Faith

House System

Extracurriculars

A Quick Look

 

Leadership & Faculty

  • Part of the Chesterton Schools Network founded by Dale Ahlquist and Tom Bengston of Minneapolis.

  • 71 Chesterton schools are operating as part of the Network in the U.S., with 22 additional schools in development. There are also sister schools in Italy, Iraq and Canada.

  • Certificate of Approval to Operate by the Maryland State Department of Education #4110

  • Our Headmaster and teachers are engaging educators, enthusiastic about the classical model, and joyful leaders— Meet them on the Faculty Page

Rooted in Faith

  • Daily Mass is the foundation of each school day

  • Curriculum inspired by G.K. Chesterton’s approach to faith and reason

  • Catholic theology integrated into each subject

  • Classical liberal arts education, the Church's time-tested approach, which formed so many leaders and saints (until the last century), has Christ, the Logos, at its center. Theology is the queen of the sciences; education is the cultivation of virtue; students understand and appreciate truth, goodness, and beauty; and all things are ordered to the honor and glory of God.

 
 

By the Numbers

  • 2025 -2026 ~ our 5th Academic Year

  • Headmaster and 11 faculty

  • 40 plus students and growing

  • More than 35 families spanning more than 10 parishes

  • Affordable tuition of $9,953 per student

Our Location

  • The Academy is located in St. Mary’s County, Maryland

  • The Parish Center at Immaculate Conception Church

  • 28299 Old Village Road
    Mechanicsville, MD 20659

  • Mailing: PO Box 310 Hollywood MD 20636

 

Graduates Ready to Lead

  • With an affordable tuition rate, an economically diverse student body, and four years of fine arts, humanities, math, and science, Chesterton Academy graduates are prepared to succeed in college and professional life. Our cohesive, content-rich curriculum unlocks student potential, expands their interests and their ability to think critically. At the center of it all is the culture of life.

  • Chesterton Academy Students go on to schools like Christendom College, Benedictine College, Notre Dame, St. Thomas, the University of Mary, Boston College, Hillsdale College, the University of Minnesota, and the Franciscan University of Steubenville.

  • Chesterton Academy Students also go on to serve in the military, enter the trades, partner with NET Ministries, or pursue religious life. One in nine male graduates enter seminary.

Chesterton schools across the country are beginning a new academic year—welcoming new students, adding grade levels, and expanding their programs. The Chesterton Schools Network is growing right alongside them, with 71 schools now in operation and 22 more preparing to open.

A warm welcome to the newest Chesterton Academies opening this year:

  • Chesterton Academy of Mater Dei – Bend, OR

  • Chesterton Academy of St. Finbar - Charleston, SC

  • Chesterton Academy of St. Thomas Aquinas - Warrenton, VA

  • Chesterton Academy of the Immaculata - Boston, MA

  • Chesterton Academy of Vero Beach - Vero Beach, FL

  • St. Clare of Assisi, a Chesterton Academy - Incline Village, NV

  • Chesterton Academy of The Divine Family - Hagerstown, MD

  • Chesterton Academy of Tokyo - Japan

Upcoming Events

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