Boys learn differently - Trinity-Pawling knows this better than any other school.
Our expertise in how boys learn best has become critically important in today's educational environment. As the experts in boys' education, Trinity-Pawling has embraced the challenges of today in order to provide a relevant education for boys.
The School has created distinctive opportunities for boys, which push back against the larger challenges facing the education of boys today.
Trinity-Pawling provides a learning environment for boys with dynamic, student-centered programs; an experiential, project-based curriculum; a culture of engagement; and established avenues for developing self-awareness and an appreciation for relationships and mutuality.
We have reimagined what is possible and developed innovative educational experiences custom-designed for boys.
With a teaching and learning model that is forward-thinking, vigorous, and engaging, Trinity-Pawling is 100% focused on providing boys with a distinctive education and a transformational experience. We are the next-generation school for boys.
Quick Stats (2025)
School News
- Senior Independent Projects: On the Frontlines of Conservation - 08/01/2025Beni Mali '25 created a 20-minute documentary as the culmination of his Senior Independent Project (SIP), drawing on his experiences working with SFW Conservation in South Africa under the mentorship ...moreof alumnus Mickey Carroll '08. He earned a Diploma of Distinction for his project and plans to return to South Africa in the summer of 2026 to continue his work with Mickey and SFW Conservation. hide
Top Rankings
Trinity-Pawling School ranks among the top 20 boarding schools (out of 278 schools) for:
Category
Attribute
Offering Breadth
School Overview
School Focus
College Preparatory
College Preparatory
Learning Difference Programs
Dyslexia / Language-based or Mild Learning Differences
n/a
Year Founded
1907
1907
Campus Size
230 acres
125 acres
Colors
Blue, Gold
First Day of School
Sat. Aug 30, 2025
Last Day of School
Fri. May 29, 2026
Student Body
Enrollment
264 students
315 students
% Students of Color
19%
26%
% International Students
15%
21%
% Students Boarding
80%
67%
Offers Post-Grad Year
Yes
No
Academics and Faculty
Saturday Classes
No
No
Student : Teacher Ratio
6:1
7:1
# of AP / Advanced Courses Offered
15
18
% Faculty with Advanced Degree
65%
72%
Summer Program Offered
No
Yes
Tuition Cost
Endowment Size
$55 million
$30 million
Yearly Tuition
(Boarding Students)
(Boarding Students)
$76,500
$68,800
Yearly Tuition
(Day Students)
(Day Students)
$54,400
(Day Student (Grade 7-8) - $37,000)
(Day Student (Grade 7-8) - $37,000)
$37,000
Yearly Tuition
(5 Day Boarding)
(5 Day Boarding)
$65,250
$49,624
% Students on Financial Aid
50%
40%
Avg. Financial Aid Grant
$32,500
$25,000
Merit Scholarships Offered
No
No
Admissions
Application Deadline
Feb. 1 / rolling
Jan. 15
Acceptance Rate
50%
64%
Director of Admissions
Jeff Beck
Associate Director of Admissions
Meredith Timone
Application URL
AP / Advanced Courses
# of AP / Advanced Courses Offered
15
18
Courses
AP BiologyAP Calculus AB
AP Calculus BCAP Chemistry
AP English Language & CompositionAP English Literature & Composition
AP Environmental ScienceAP Macroeconomics
AP MicroeconomicsAP Music Theory
AP Physics 1AP Physics C: Mechanics
AP StatisticsAP Studio Art
AP U.S. History
Sports
# Interscholastic Sports Offered
17
16
Extracurriculars
Total Extracurricular Organizations
51
23
Extracurriculars
Club or Organization:
Arts and Music Programs:
Recreational Athletic Programs:
3D Printing ClubAcolytes & Vergers
Asian SocietyBaking Club
Bridge ClubCheese Club
Chess ClubCoffee and Tea Club
Computer Programming ClubCooking Club
Deans AssistantsDebate Club
Diversity ClubDog Walking Club
Dorm ProctorsDungeons and Dragons
Environmental CouncilFinance Club
Literary ClubMath Club
Mindfulness ClubMock Trial Club
Poker ClubRandom Acts of Kindness Club
ReadingRelay For Life
Spirit ClubStrategy Board Games
Student ActivitiesStudent Senate
Student's CornerThe Phoenix School Newspaper
Usher ClubVital Signs Science Magazine
Arts and Music Programs:
Recreational Athletic Programs:
College Matriculation
School Notes
- 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 275 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, 15 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.
- Experiential learning is just the beginning. Our three-part Practicum for Civic Leadership fosters problem-solving skills, promotes interdisciplinary exploration, and builds authentic communication skills. Through the Winter Project, Global Collaborative Challenge, and Senior Independent Project, we place our students at the center of the learning process. They become active participants and co-creators - in and out of the classroom. Using a multi-disciplined approach and engaging with the world outside of Trinity-Pawling, students work collaboratively to understand issues, give oral presentations both as part of a group and as an individual, and learn how to ask the right questions when confronted with challenges. The three-pronged, multi-dimensional Practicum challenges every student to master these 21st-century skills.
- The School`s Center for Learning Achievement recognizes the potential in each and every student. For over 50 years, this signature program and individualized academic support has provided an environment where students are transformed - achieving their academic goals in ways they never expected, finding their confidence, and preparing for their futures.
- LD types supported: Dyslexia / Language-based or Mild Learning Differences
- Trinity-Pawling School accreditations: New York Association of Independent Schools and New York State Board of Regents
- Sample of notable school alumni/alumnae:
- Christopher Wren ’54 - Retired from The New York Times after nearly twenty-nine years as a reporter, foreign correspondent, and editor. He is the author of Those Turbulent Sons of Freedom and Walking to Vermont.
- Paul Rachman ’78 - Is an American film director who directed the highly praised 2006 documentary American Hardcore, which premiered at the Sundance Film Festival and was released by Sony Pictures Classics.
- Andrew Masset ’67 - Is an actor, known for Halt and Catch Fire, Remember the Titans, and Kill the Messenger.
- Michael Melford ’68 - Is an American photographer, artist and teacher known for his National Geographic magazine assignments.
- Joseph Callo ’48 - Is a Naval History Magazine Author of the Year. His most recent book is a memoir titled The Sea Was Always There. His book John Paul Jones: America’s First Sea Warrior is the 2006 winner of the Samuel Eliot Morison Award by the Naval Order of the US
- Chukky Okobi ’96 - NFL football player, Pittsburgh Steelers, 2001–07, Super Bowl XL Champion
- Maurice Vaughn ’86 - MLB first baseman, three-time All-Star, AL MVP
- Gil Junger ’72 - Is an American director for Touchstone Pictures, most famous for 10 Things I Hate About You
- Shayne Skov ’09 - American NFL football player, San Francisco 49ers
- Ray Davis ’18 - American NFL Football, Buffalo Bills
- School Motto: Fides Et Virtus
- School Mascot: The Pride
Source: Verified school update
Frequently Asked Questions
How much does Trinity-Pawling School cost?
Trinity-Pawling School's tuition is approximately $76,500 for boarding students and $54,400 for day students.
What is the acceptance rate of Trinity-Pawling School?
The acceptance rate of Trinity-Pawling School is 50%, which is lower than the boarding school average of 64%.
Who are famous alumni from Trinity-Pawling School?
Trinity-Pawling School famous alumni include: Christopher Wren ’54, Paul Rachman ’78, Andrew Masset ’67, Michael Melford ’68, Joseph Callo ’48, Chukky Okobi ’96, Maurice Vaughn ’86, Gil Junger ’72, Shayne Skov ’09 and Ray Davis ’18.
What sports does Trinity-Pawling School offer?
Trinity-Pawling School offers 17 interscholastic sports: Baseball, Basketball, Cross Country, Cross Country Running, Football, Golf, Ice Hockey, Lacrosse, Mountain Biking, Soccer, Softball, Squash, Tennis, Track, Track and Field, Ultimate Frisbee and Wrestling.
What is Trinity-Pawling School's ranking?
Trinity-Pawling School ranks among the top 20 boarding schools for Most extracurriculars offered.
When is the application deadline for Trinity-Pawling School?
The application deadline for Trinity-Pawling School is Feb. 1 / rolling (applications are due on Feb. 1 but additional applications are reviewed year-round as space permits ).
Alumni Reviews Review School
Review
Description
Trinity-Pawling School Alumni #1
Class of 1980
5.0010/21/2021
University of Denver, western state university-law
Class of 1980
5.0010/21/2021
University of Denver, western state university-law
Lots of personal attention from faculty both during class and after class.
Fantastic selection of competitive sports available. . .
Related Schools
Show me:
People that viewed Trinity-Pawling School also viewed these schools: Salisbury School, Avon Old Farms School, Canterbury School, Berkshire School and Choate Rosemary Hall.
The nearest boarding school to Trinity-Pawling School is Canterbury School (9.5 miles away)
School
Location
Miles
Grades
Students
319 students 31.5 miles 251 Canaan Road
Salisbury, CT 06068
(860) 435-5732
Salisbury, CT 06068
(860) 435-5732
31.5
9-12, PG
319
405 students 41.7 miles 500 Old Farms Road
Avon, CT 06001
(800) 464-2866
Avon, CT 06001
(800) 464-2866
41.7
9-12, PG
405
332 students 9.5 miles 101 Aspetuck Avenue
New Milford, CT 06776
(860) 210-3832
New Milford, CT 06776
(860) 210-3832
9.5
9-12, PG
332
430 students 38.8 miles 245 North Undermountain Road
Sheffield, MA 01257
(413) 229-1003
Sheffield, MA 01257
(413) 229-1003
38.8
9-12, PG
430
867 students 41.4 miles 333 Christian Street
Wallingford, CT 06492
(203) 697-2239
Wallingford, CT 06492
(203) 697-2239
41.4
9-12, PG
867
Recent Articles
How to Choose the Right Performing Arts Boarding School: A Checklist for Parents and Students
Every year, thousands of gifted young artists apply to top performing arts boarding
schools, yet most families approach the selection process without a clear roadmap. Knowing what to look for—from teacher qualifications to alumni success rates—makes all the difference in finding a program where you can truly flourish.
The Boarding School Glossary
Boarding schools have their own jargon just like any activity or affinity group has.
A Glimpse into Boarding School Life at Hawai‘i Preparatory Academy
One of the most common questions families ask when exploring boarding school options is: What does a typical day look like for a student? Beyond academics, they want to understand how students live, learn, and grow within the community—how daily routines shape not only their education but also their independence, friendships, and character.
