News and Events



Monday October 28th – Socratic Seminar Series – 9:00-10:30am

Friends and families of Chesterton Academy of Annapolis are invited to join Socratic Seminars on different discipline.

351 Dubois Road, Annapolis, MD 21401


June 2019

January 2019

We are proud to introduce the school’s new Executive Director, Mr. Ron George!!!!

Ron George has a Bachelors Degree from Syracuse University and a Masters in Clinical Psychology from The Institute for Psychological Sciences which is now Divine Mercy University. For several years he taught 11th and 12th graders Apologetics and Catechetical Studies. He and his wife Becky were pioneers in homeschooling and he assisted Becky in the Homeschooling of their six children.  Mr. George is the President of Ron George Jewelers and has always been an active member of the community, including serving as a Founder and Executive Director of the Center for Family Development, providing youth programs, counseling services, and spiritual retreats. In his twenties, he counseled at Covenant House in New York City assisting teen run-a-ways and “push-outs”. He served 8 years as a legislator in the Maryland State House, a ranking member of the Education Subcommittee, often protecting Homeschooling, Charter Schools, and small private schools.

January 2019

We are so blessed to announce that Father Daniel Vitz, IVE will be the school’s chaplain!  Father Dan is a missionary priest with the Institute of the Incarnate Word.

December 2018

Chesterton Academy of Annapolis appears in the November-December issue of Defend Life newsletter.

November 29, 2018

Chesterton Academy of Annapolis is proud to announce its first headmaster, Mrs. Mary Toffolo-Cresce!!!

September 4th, 2018:

First day of school!  Starting with daily mass followed by blessing of students and teachers at school location.  First class? Philosophy taught by Sr. Mary of Incarnate Word.

August 22, 2018:

We are launching!!!! We have 12 students and all of our incredible teachers.  What an amazing journey since Feb 9th, 2018 when Holy Spirit moved us to take on this endeavor.  Thank you for all your support and prayers.  Please continue to pray for us to do God’s will.

August 13, 2018:

Click here to hear Bill Cleary’s interview with Guadalupe Radio!

July 18, 2018:

Another generous donor has offered a matching donation of $3000!!!  Our total matching donation is $33,000 and we have been able to raise a large amount and hope to match the rest of it.  Thank you to our supporters who believe in this school and how it will shape and form the mind and soul of future students!

July 17, 2018:

Servants of the Lord and of the Virgin Matara have been praying for Chesterton Academy of Annapolis from the start of the effort.  Now, they have offered a philosophy teacher for the school for academic  year 2018’19.  Sr. Mary of Incarnate Word, SSVM received her BA in History from Caldwell University and has taken graduate level courses in Metaphysics of St. Thomas Aquinas from The Catholic University of America.  Visit our Faculty page for her full bio.  She will be joining us this Fall to teach our students the classical philosophers such as Plato and Aristotle and help instill the “love of wisdom” in our youth with her natural joy and enthusiasm!!!

July 14, 2018:

Chesterton Academy of Annapolis announces its partnership with Classical Learning Test (CLT) and will be using CLT’s exam as placement test for all students wishing to enroll.   CLT’s college entry exam will be offered to Chesterton Academy of Annapolis students in their Sophomore and Junior year.  This is a valued partnership as CLT has grown tremendously in a short time. Its college entry exam is accepted by more than 120 colleges around the country and its placement test is accepted by over 300 high schools across the nation.  And their numbers continue to grow.

July 13, 2018:

Maryland Catholic Homeschoolers (MCH) umbrella group extends its membership to families enrolled at Chesterton Academy who are homeschooling their other children.  This is a tremendous opportunity for siblings of Chesterton Academy of Annapolis students to be part of a large network of Catholic homeschooler.

July 12, 2018:

More than 1/5 of our 30K matching donations was matched in one week!!!   Please support us by helping our school take advantage of this generous donation! Donate now!

June 29, 2018:

Successful information night with our special guest, Colleen Richards, Headmaster of Chesterton Academy of Rochester.   Many interested families and students ranging form 9-12th grades were able to ask questions and picture the opportunities Chesterton Academy of Annapolis will offer specially in the first year.

June 20, 2018:

After consulting with co-founders of Chesterton Academy of Holy Family who successfully launched 9th-12th in 2014 and has already grown to almost 60 students, we have decided to open enrollment to all grades for Fall of 2018.  Contact us for more information.

June 18, 2018: $30,000 has been offered in Matching Donations!

Please help the Chesterton Academy of Annapolis to make the most of this opportunity and Donate now

June 10, 2018: Generous donor has offered to pay for all Fall of 2018 students books and up to $200 of each students uniform!!!

May 31, 2018: Open House: This open house covered many common questions at this stage in our development:

Location: The school will be located at 351 Dubois Rd., Annapolis, MD 21401. This is the Annapolis Friends Meetinghouse located on 4.5 acres in a quiet residential neighborhood just a few blocks behind St. John Neuman Church. It is a modern facility, handicap accessible, and 100% solar powered. We appreciate this Quaker community’s support, and they are excited to support our school.

Teachers: The Chesterton Academy of Annapolis in its first year will be taught with one full time teacher and a group of part-time teachers who will teach various subjects. In following years, the staff will shift to more full-time teachers as enrollment grows. The school is excited to announce our first 2 teachers selected for our Fall 2018 start:

Tim Feeney has over 17 years of Classical teaching experience including 14 years at the nearby Rockbridge Academy during its early and growth years. He will teach Humanities, Philosophy, and possibly other subjects.

Naomi Popp will be the Art Teacher. She explained her love of art and how important an integrated understanding of other subjects, such as math and science, is to art to provide proper perspective. She sees Classical Education as the best option for integrated learning.

The school is in discussion with several other teachers complete the needs for its first year.

Support of the Archdiocese of Baltimore: Early in the schools planning, the founders met with and have update the Archdiocese. Archbishop Lori has informed us that he is familiar with the Chesterton school model, he found our methods sound, and he asked us to inform the local parishes of our efforts. The school continues to update and keep in contact with the Archdiocese.

Support of a Religious Order: The Institute of the Incarnate Word (IVE) and, and their sister order, The Servants of the Lord and the Virgin of Matara have pledged their prayers and support. Father Diego Ruiz, IVE spoke about the importance of schools in evangelizing and forming the youth. Two sisters of the Servants of the Lord were also in attendance. They were there to answer questions about their Classical Education experience at St. Jerome Elementary School in Hyattsville, MD.

Why Classical Education? Ruth Popp of St. Thomas Aquinas Tutorial gave a very informative talk about Classical Education.

March 9, 2018:

Meeting of Interested Friends, Teachers, and Supporters: This meeting built on our first meeting and included our guest speaker, Dale Ahlquist. Dale is the President of the American Chesterton Society, and co-founded the Chesterton Academy in 2008. Within 5 years, other groups across the country started asking for his support in starting similar schools in their cities. Collectively these 9 schools and one in Italy form the Chesterton Network of Schools which work together to provide the calassical curriculum and a strong foundation to support each other. There are 5 new school planning to open in Fall of 2018. At Chesterton Academy of Annapolis, we are not looking at create a new school, but instead are building a school based on a model that has been successful and duplicated over the years.

February 9, 2018:

Our First meeting of Friends, Teachers, and Supporters: This meeting had a good crowd to learn about our school plans and to help us start the process towards a Fall 2018 launch. The guest speaker was Jeremy Tate, President of CLT: Classical Learning Test. Jeremy explained importance and draw towards Classical Education and its growth and acceptance by Colleges in the last decade.   CLT was founded in 2015, and its Classical Learning Test is an alternative to the SAT and ACT. As of February 2018, the CLT is now accepted by over 85 Colleges and Universities in their Admissions Process. In just a few short years, this is significant acceptance by established universities of the Classical Education model.