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Trinity-Pawling School

At Trinity-Pawling, everything we do is shaped to the needs of boys in the 21st century. We teach and learn from experience. Our programs are active and applied — packed with opportunities for hands-on learning. We reimagine what’s possible in boys’ education. The results are transformational.



Trinity-Pawling offers a personal educational experience to 300 boys in grades 7-12 and postgraduates. The School delivers entrepreneurial and ambitious programs that provide opportunities for collaboration and camaraderie, independent exploration, and the discovery of passions and talents. With over 100 academic courses, 18 AP courses, 13 athletic teams competing in the New England Founders League, and a multitude of extracurricular activities, our students have many opportunities to reimagine and own their education.

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City: Pawling, NY

Year Founded: 1907

Campus Size: 230 Acres

Grades Offered: 7th-12th, PG

Number of Students: 300

Percent Boarders: 82%

Average Class Size: 11

Gender: Male

Diversity: 20+ States & 21 Countries represented



Signature Program: Institutes for Active Learning, Wintersession, The Center for Learning Achievement