Upcoming Events
Thursday Night Book Club
This month we will be reading The Napoleon of Notting Hill by G.K. Chesterton. Our meeting will take place at 25 Clinton St (the school building) at 7pm. Come join us for lively conversation, good company, and great books! Our book club explores classic works of literature through the lens of faith, seeking to discover the truth, beauty, and wisdom woven into these timeless stories. All are welcome - even if you haven’t finished the book!
RSVP to jdinnocenzo@chestertonimmaculata.org
Mass of the Holy Spirit
Join us on Saturday, September 26 at 11:00 AM for our Mass of the Holy Spirit, celebrated by Father Thomas Sullivan, as we ask the Holy Spirit to guide our students, faculty, families, and entire school community throughout the year ahead. Lunch reception following.
Open House
Discover Chesterton Academy at our Open House. Meet our faculty, staff, and families and learn more about our joyfully Catholic, classical high school.
Bourbon &Burn
For the guys…Bourbon & Burn is back. Join our chaplain, Fr Sinisa, headmaster Josef Cressotti, and Chesterton Dads Jamie Walsh and Dan D’Innocenzo for spirits and cigars at the St. Thomas the Apostle Rectory in Millis. Sample one of our bottles or bring your favorite to share. Good food and great conversation in the spirit of our patron G.K. Chesterton.
RSVP to any of the men listed above or email
info@chestertonma.org
Middle School Nerf Wars: Battle of Lepanto Edition
It's the Holy League vs. the Ottoman Empire! Middle Schoolers are invited to battle it out at the Crusaders Gym. We will finish with a rosary.
B.Y.O.G.
Standard ammo provided
Wednesday, October 7, 2026
6:30 - 8 pm
Fill out our admissions interest form and receive VIP status - extra ammo & side choice.
Newman Guide College Fair
What if your college experience could deepen your Catholic faith rather than challenge it?
Join us at Chesterton Academy of the Immaculata on Friday, October 9 at 7:00 PM for a Newman Guide Catholic College Fair, featuring colleges recommended by The Newman Guide to Choosing a Catholic College.
This special evening is an opportunity for high school students and their parents to learn more about faithful Catholic colleges and universities that seek to integrate faith, reason, academics, community, and Catholic life.
Representatives from Newman Guide colleges will be available to meet with families, answer questions, and share information about their academic programs, campus life, Catholic formation, admissions, and opportunities for students.
Please register here
Pumpkin Carving & Country Dance
Saddle up for a gourd time! Come & carve the pumpkin of your choice to light up your Halloween night. We’ll end the night learning some country line dancing, so don’t forget your boots! Pumpkins, tools, & music provided. 7-9pm at 25 Clinton St., Framingham) RSVP to jdinnocenzo@chestertonimmaculata.org
Curriculum Night
Go beyond the brochure and discover the Chesterton difference. At Curriculum Night, families will have the opportunity to step into the classroom, meet our faculty, and discover how our classical curriculum forms students in truth, goodness, and beauty.
Explore how faith and reason work together throughout the curriculum—from theology and the great books to mathematics and science, where students are encouraged to ask big questions, think critically, and seek the truth.
Ladies Bunco Night
Join us at Chesterton Academy for a fun filled evening of Bunco, laughter, and fellowship! No experience needed, just a little friendly competition. The games begin at 7pm at our school building (25 Clinton St, Framingham). If you’d like to join, please RSVP to office@chestertonimmaculata.org
The Story of Everything Screening
The Story of Everything is a cinematic exploration of the cosmos that reveals the hidden hand behind our universe. From the precise laws that govern the stars to the intricate patterns found in every living cell, the film traces evidence of intentional design throughout nature. Whether examining distant star-forming clouds or the spiral structure of DNA, we discover a consistent signature woven into the fabric of existence.
Back to School Bingo Night
Summer might be ending, but the fun is just beginning at Chesterton Academy! Join us for Bingo Night and win some great school goodies! Bring the whole family, all ages can play. Pizza and refreshments will be served, $10 a family. RSVP to jdinnocenzo@chestertonimmaculata.org
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Line Dancing
Grab your friends and join us for a fun-filled Teen Line Dancing Night! Whether you’ve danced before or have two left feet, everyone is welcome. We’ll teach the steps, play great music, and have refreshments ready for your enjoyment. Meet at the St. Thomas Large Hall from 7-9pm. For grades 7 and up.
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Thursday Night Book Club
Join us for a relaxed and engaging evening where faith and great literature come together. Through engaging discussion, we will explore classic novels that deepen our understanding of faith, the human person, and the pursuit of truth, goodness, and beauty. Whether you’re a lifelong reader or simply curious to learn more, all are welcome. You can RSVP to office@chestertonimmaculata.org
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Summer Basketball Clinics
Sign Up Here
36 Clinton St. | Framingham
Tuesdays 7:00-8:30 pm
$150 per player for 6 sessions
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 4 - 12
Thursday Night Book Club
Come join thoughtful conversation, fellowship and the shared pursuit of truth, goodness, and beauty.
Our first book will be The Man Who Was Thursday by G.K. Chesterton
RSVP at office@chestertonimmaculata.org
Teen Country Line Dancing @ St. Thomas
Teen Country Line Dancing at St. Thomas in Millis
Yeehaw! Teens are invited to a Country Line Dancing Party hosted by Chesterton Academy of the Immaculata!
Join us for a night of music, dancing, games, snacks, and fun with friends at St. Thomas the Apostle in Millis. No experience needed ..we’ll teach the dances!
📍 St. Thomas the Apostle
Large Hall, 974 Main Street, Millis
📅 July 11
🕖7-9 pm
👢 Western attire encouraged!
Bring your friends and come ready for a great night of fellowship and dancing!
Summer Basketball Clinics
Summer @ Chesterton
Basketball Clinic
We are excited to offer two 6 week basketball clinics this Summer. Beginning on June 16
36 Clinton St. | Framingham
Tuesdays 5:30-7:00 pm
$150 per player for 6 sessions
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 7 - 11
Summer Basketball Clinics
Summer @ Chesterton
Basketball Clinic
We are excited to offer two 6 week basketball clinics this Summer. Beginning on June 16
36 Clinton St. | Framingham
Tuesdays 5:30-7:00 pm
$150 per player for 6 sessions
Skill Development
Improve fundamentals in shooting, dribbling, passing & footwork
Basketball IQ
Learn the game the right way with smart decisions
Compete with Heart
Build toughness, confidence & a strong work ethic
Faith. Friendship. Excellence.
We form better players and better men and women on and off the court
Open to Boys & Girls
Grades 7 - 11
Chesterton's Birthday Celebration
“The first fact about the celebration of a birthday is that it is a way of affirming defiantly, and even flamboyantly, that it is a good thing to be alive,” — G.K. Chesterton
Come celebrate our patron GK Chesterton's Birthday with us on May 29 - Family BBQ & Dance. Music, Dancing, Games & more! #bostoncatholic #gkchesterton #catholicmom #classicaleducation Please RSVP!
Star Party
*** Date Change ***
Join us for an evening under the stars at Chickering Playing Fields in Dover. Star Party begins at 9:15 pm on Saturday, May 16. Open to the Chesterton Academy community. Snacks served!
Thank you to Dr. Scott Rottinghaus for providing the telescope.
Cultura Vitae Speaker Series
Chesterton Academy of the Immaculata presents its Cultura Vitae Speaker Series on Wednesday, May 13, 2026 at 7:00 PM. Myrna Maloney Flynn of Massachusetts Citizens for Life will give a talk titled “Forming Courageous Hearts: Forming the Next Generation of Pro-Life Leaders.”
This event is free and open to the public.
Please register to attend here.
Homeschool Enrichment: Drama Workshop and Field Day
Rising 8th through 12 grade homeschoolers are invited to Chesterton Academy on May 13. Drop off at 8 am to attend Mass with us at St. Stephen’s Parish. In the morning will be a drama workshop, followed by lunch, and a friendly field day competition.
RSVP to the office@chestertonimmaculata.org or (508) 834-9849.
Coffee & Donuts
Chesterton Academy will be hosting Coffee & Donuts. Representatives from the school and information about the school will be available!
Hoops & Hoosiers
CAIM students, Basketball Club, prospective students and friends are invited to the St Stephen gym for pick up game, pizza, and movie night!
rsvp: office@chestertonimmaculata.org
CLT @ Chesterton Academy
Juniors & Seniors are invited to take the CLT exam at Chesterton Academy with our students.
Accepted Students Night
Accepted and current students and their families are invited for a dinner in their honor at Chesterton Academy of the Immaculata. We will have a special guest with us - Dale Ahlquist - Author and Founder of the Chesterton Schools Network!
Admissions Decisions
Admissions Decisions for our Class of 2030 and 26-27 transfers will be delivered via email on this day followed by a formal letter!
Winter Wonderland Dance
Chesterton Academy of the Immaculata
School Gym | 36 Clinton St.
Step into a magical evening at Chesterton Academy’s Winter Wonderland Dance!
Upstairs, high school students will dance the night away with friends amid twinkling lights and festive music.
Grades 9-12 only.
$10 per person
Priority Application Deadline
Submit your application by this date to have a priority review of your application and decision by February 28. Applications submitted after this date will be considered on a rolling basis.
Open House
Join us for the last open house before our priority application deadline. A brief program will begin at 6:15 followed by guided tours of our space. Come discover the Chesterton Difference!
CLT-8 Exam @ Chesterton Academy
8th graders are encouraged to register to take the CLT-8 Placement Exam at Chesterton Academy. The exam is approximately 2 hours long with breaks provided between sections. This test is offered for free and high scores are eligible for Chesterton Academy scholarships. More information about the test can be found on our admissions page here.
Advent Lessons & Carols
Please join Chesterton Academy of the Immaculata for our Advent Lessons & Carols, a cherished tradition of Scripture readings, choral music, and prayerful anticipation of the Nativity of Our Lord.