Dr. Josef Cressotti named Headmaster of Chesterton Academy of the Immaculata
Framingham, MA — May 1, 2026 — Feast of St. Joseph the Worker
Chesterton Academy of the Immaculata is pleased to announce the appointment of Dr. Josef Cressotti as its new Headmaster.
Dr. Cressotti joined the Academy following distinguished service at St. Sebastian’s School in Needham, Massachusetts, where he served as Chair of the Religion Department and Varsity Cross Country Coach. He is known for his dedication to academic excellence and the integral formation of students.
“I’m excited to welcome an educator of Dr. Cressotti’s caliber and experience,” said Nathalie Calvo, Board Chair. “The Board is looking forward to supporting his leadership at Chesterton Academy of the Immaculata.”
Dr. Cressotti will begin his tenure as Headmaster on July 1, 2026.
Josef Cressotti grew up in Western Massachusetts, where he graduated from Holyoke Catholic High School in 1995. Having studied film at Yale, Josef worked in the documentary film industry in New York and Los Angeles for three years before going to Scotland to study philosophy at the University of Glasgow in 2002. Josef continued his studies at the University of California, Riverside, where he completed a dissertation on Immanuel Kant. For the past fourteen years, Josef has taught philosophy, religion, and Latin at St. Sebastian’s School in Needham, becoming the Chair of the Religion Department in 2020. A lifelong runner with 11 marathons under his belt, Josef coached the Varsity Cross Country team at St. Sebastian's for eight years.
“I am thrilled to join the Chesterton Academy of the Immaculata. Ever since I read Orthodoxy at the conclusion of graduate school, I have been attracted to Chesterton’s vision of education – the systematic development of all the faculties of the human person to the end of knowing God. It is a great honor to participate in an institution dedicated to realizing this vision and making possible a more joyful life for young people.”
As Headmaster, Dr. Cressotti will oversee the academic and spiritual life of the Academy, working closely with faculty, families, and the Board to advance its mission. Chesterton Academy of the Immaculata, located in Framingham, Massachusetts, is part of a growing network of joyfully Catholic, classical high schools. The Academy partners with parents to provide a rigorous classical education animated by the Catholic faith, forming young men and women to pursue truth, goodness, and beauty and raise up the next generation of joyful leaders and saints.
For more information about Chesterton Academy of the Immaculata, please visit chestertonimmaculata.org or contact office@chestertonimmaculata.org