Boys learn differently - Trinity-Pawling knows this better that 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 these challenges of tomorrow in order to provide a relevant education for boys today.
The School has created distinctive opportunities for boys, which pushes 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
- - 08/01/2025eni 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 279 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
Student Body
Enrollment
264 students
315 students
% Students of Color
19%
27%
% International Students
15%
21%
% Students 51³Ô¹ÏÍø
80%
67%
Offers Post-Grad Year
Yes
No
Academics and Faculty
Saturday Classes
No
No
Average Class Size
10 students
12
* National Avg. »
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
(51³Ô¹ÏÍø Students)
(51³Ô¹ÏÍø Students)
$76,500
$68,420
Yearly Tuition
(Day Students)
(Day Students)
$54,400
(7th & 8th Grade Day - $37000)
(7th & 8th Grade Day - $37000)
$36,400
Yearly Tuition
(5 Day 51³Ô¹ÏÍø)
(5 Day 51³Ô¹ÏÍø)
$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 Biology, AP Calculus AB, AP Calculus BC, AP Chemistry, AP English Language & Composition, AP English Literature & Composition, AP Environmental Science, AP Macroeconomics, AP Microeconomics, AP Music Theory, AP Physics 1, AP Physics C: Mechanics, AP Statistics, AP 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 Club, Acolytes & Vergers, Asian Society, Baking Club, Bridge Club, Cheese Club, Chess Club, Coffee and Tea Club, Computer Programming Club, Cooking Club, Deans Assistants, Debate Club, Diversity Club, Dog Walking Club, Dorm Proctors, Dungeons and Dragons, Environmental Council, Finance Club, Key Club, Knitting Club, Literary Club, Math Club, Mindfulness Club, Mock Trial Club, Model UN, National Honor Society, Poker Club, Random Acts of Kindness Club, Reading, Relay For Life, Spirit Club, Strategy Board Games, Student Activities, Student Senate, Student's Corner, The Phoenix School Newspaper, Usher Club, Vital Signs Science Magazine
Arts and Music Programs:
Recreational Athletic Programs:
College Matriculation
College Acceptance Rate
100%
10 Most Popular College Choices (# Enrolled)
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 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.
- 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 recognizes the potential in each and every student. For over 45 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
- 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 and Shayne Skov ’09.
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. . .
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