Upcoming Events
School Retreat
Student Retreat: Encountering Christ in Scripture and Sacrament
September 26–28, 2025
Led by Brother Hector, O.S.B., and Sister Kerry Smith, OblSB, this weekend retreat at St. Leo Abbey offers students a time of spiritual renewal through prayer, Scripture, and the sacraments. With oversight by Dr. Jonathan Day and faculty chaperones, the retreat fosters deep reflection and Catholic fellowship.
Departure: Friday at 12:45 PM
Return: Sunday at approx. 3:00 PM
Location: St. Leo Abbey Retreat Center, Saint Leo, FL
Cost: No additional cost to students
Florida Chesterton Gathering in Orlando
Florida Chesterton Academy Gathering – Orlando
October 20–21, 2025
Chesterton Academy of Orlando is hosting us for a two-day gathering of Florida Chesterton schools for fellowship, joyful competition, shared prayer, and celebration. Highlights include House competitions, a potluck dinner, a student dance, mock seminars, and school Mass.
Location: Chesterton Academy of Orlando
Departure: Monday, October 20 at 10:30AM
Return: Tuesday, October 21 at 3:00PM
New Faculty Orientation
The headmaster welcomes and orients the new faculty to the school!
CSN Summit 2025
Our teachers, headmaster, and two school Board Members are heading to New Orleans to continue our development as educators and receive accreditation from the Chesterton Schools Network!
CAO Shadow Day
See a typical school day in a Chesterton Academy and participate in Mass by visiting Chesterton Academy of Orlando!
CAVB Information Session (Zoom)
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
21st Amendment Distillery CAVB Fundraiser
Mark your calendars and join us at 21st Ammendment Distillery for our CAVB Fundraiser!
CAVB Information Session (Zoom)
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
Meet the Headmaster
Gather with our team as we welcome our new headmaster, Dr. Jonathan Day!
CAVB Information Session (Zoom)
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
CAO Shadow Days
See a typical school day in a Chesterton Academy and participate in Mass by visiting Chesterton Academy of Orlando!
CAO Shadow Day
See a typical school day in a Chesterton Academy and participate in Mass by visiting Chesterton Academy of Orlando!
CAVB Back to School BBQ
Join us for a BBQ to mingle with the friends and potential families of Chesterton Academy of Vero Beach!
CAVB Information Session
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
CAVB Information Session
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
CAVB Information Session
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
CAVB Information Session
Join members of our founding team to learn more about the school. Informational material will be available, as well as the opportunity to ask questions. Please join us!
Chesterton Rosary Society
Join members of our founding team to ask Our Lady’s intercession for the Chesterton Academy of Vero Beach, and learn more about the school.
Information Session
Join us for our third information session about the Chesterton Academy of Fort Worth. If you plan to attend, please RSVP by filling the form below or email info@chestertonacademyfw.org