Trinity-Pawling School (Top Ranked Private School for 2025)

700 Route 22
Pawling, NY 12564

Trinity-Pawling School Photo #1 - There are countless opportunities for students to develop leadership skills at Trinity-Pawling. Our community is intentionally designed to unleash the full potential of each student. Classes, clubs and activities, dorms, community service, and athletics are all venues for students to assume both official and unofficial positions of leadership, build their confidence, and become effective role models.

Trinity-Pawling School Photo #2 - Boys find a home away from home on Trinity-Pawlings active 230-acre campus overlooking the Hudson River Valley, just 60 miles north of New York City.

Trinity-Pawling School Photo #3 - Our student-athletes range from lifelong players to novices - everyone plays sports at their level of experience and ability. The Pride competes in the Founders League, a highly competitive prep-school arena where student-athletes are prepared for college-level competition.

Trinity-Pawling School Photo #4 - Make yourself at home at Trinity-Pawling. And then leap out of your comfort zone. As a brotherhood, we're a caring community that will push you to be nothing short of extraordinary.

Trinity-Pawling School Photo #5 - During Saturday Programming each week, students have their choice of exciting and challenging learning experiences that follow a track of immersion in one of the four Institutes for Active Learning: Leadership, Citizenship, Entrepreneurship, and Environmental Stewardship. These four cornerstones propel the development of other critical skills for 21st-century learners.

Trinity-Pawling School Photo #6 - The Smith Field House is a 20,000-square-foot facility, which houses a gymnasium, two full basketball courts, an additional half court and workout area, locker rooms, a trophy area, and an Athletic Hall of Fame room. The building not only serves as a state-of-the-art athletic facility, but is also enjoyed daily as a student social center and gathering space.

Trinity-Pawling School Photo #7 - We prepare our students to be in charge of their own learning and their future accomplishments. The School's focus on effort fosters the self-awareness that allows students to recognize the areas where they need to grow - while at the same time, opening their eyes to the talents and potential they never thought possible.

Trinity-Pawling School Photo #8 - One of the School's most distinctive attributes is its signature program, The Effort Challenge (TEC). Each boy at Trinity-Pawling is recognized and assessed in terms of the effort he devotes to a given endeavor. The learning objective inherent in this ethos of effort is to teach young people that the more they invest of themselves the greater their accomplishments will

Trinity-Pawling School Photo #9 - Each year, students with learning differences graduate from Trinity-Pawling prepared for college and beyond. The School`s Center for Learning Achievement recognizes the potential in each and every one of these students. For over 50 years, this signature program and individualized academic support have been providing an environment where students are transformed.

Trinity-Pawling School Photo #10 - Our instructors are teachers and accomplished professional artists who are active in their fields. You'll learn from the best, and you'll do it in our Arts Center, a showpiece in itself, which houses a 400-seat theater, state-of-the-art sound system, rehearsal spaces, and practice rooms so you can discover and nurture your passions.

Trinity-Pawling School Photo #11 - At Trinity-Pawling, we intentionally design our programs to engage, inspire, and challenge boys. Our commitment to experiential learning acknowledges the research that has proven to be successful for boys. Our vigorous, yet supportive learning environment encourages boys to invest in themselves, discover their gifts and talents, and unlock their full potential.

Trinity-Pawling School Photo #12 - Gardiner Library and Learning Commons is the center of design thinking on campus, with a skilled staff who facilitate student collaboration.

Trinity-Pawling School Photo #13 - At Trinity-Pawling, you are surrounded by a welcoming and supportive community where you'll feel right at home. From your teachers and dorm parents to your peers, you'll have mentors every step of the way.

Trinity-Pawling School Photo #14 - At Trinity-Pawling, innovation is a key component of our curriculum. Every day, faculty and students engage in hands-on learning, creating, and collaborating.

Trinity-Pawling School Photo #15 - At Trinity-Pawling, character matters.

Trinity-Pawling School Photo #16 - The pride runs deep.

Trinity-Pawling School Photo #17 - Trinity-Pawling has a long history of outdoor education, including a pond house classroom, hiking trails, working farm, and campus campsite.

Trinity-Pawling School Photo #18 - Through our Environmental Stewardship Institute, campus farm, and service projects, students work together to steward our natural resources.

Trinity-Pawling School Photo #19 - Our campus includes ponds, fields, and trails. You can fish, bike, run, hike, and explore here!

Trinity-Pawling School Photo #20 - At Trinity-Pawling, we offer an exceptionally long list of extracurricular activities - opportunities for students to learn new things.

Trinity-Pawling School Photo #21 - Our student-athletes range from lifelong players to novices - everyone plays sports at their level of experience and ability.

Trinity-Pawling School Photo #22 - At Trinity-Pawling, your sport of choice can be Varsity Farming! The farming program centers on the concepts of sustainability and stewardship of the land through campus-based food production, composting, recycling, and renewable energy.

Trinity-Pawling School Photo #23 - Our arts program is innovative, inclusive, and engaging - you'll want to be part of it!

Trinity-Pawling School Photo #24 - A Trinity-Pawling education gives boys the confidence to try and the courage to create.

Trinity-Pawling School Photo #25 - The next-generation school for boys is here, on a campus that feels warm and welcoming and human-scaled, in an academic community that thinks ahead, looks forward, and gets transformational results.

Trinity-Pawling School Photo #26 - Our fine arts courses aim to inspire and allow students to dive into a medium that supports their interests and experience, with an array of choices from foundation-level to advanced.

Trinity-Pawling School Photo #27 - The boarding experience at Trinity-Pawling is designed to help students develop a sense of responsibility, self-sufficiency, connectedness, and lifelong friendships. They gain confidence and a better understanding of what it means to live and thrive in a community.

Trinity-Pawling School Photo #28 - Wintersession at Trinity-Pawling is a two-week student-centered experiential learning session held between Thanksgiving and Winter Break. It gives students the opportunity to participate in a multi-disciplined project of their choosing with a Winter Project; a dynamic, immersive study of real-world problems with the Global Collaborative Challenge (GCC); or an in-depth exploration of a personal interest with the Senior Independent Project.

Trinity-Pawling School Photo #29 - 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.

Trinity-Pawling School Photo #30 - We give boys the environment to focus, the support of a community that understands them, and the opportunity to thrive.

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)

Top Ranked NY School
Grades: 7-12
Enrollment: 264 students
Yearly Tuition: $76,500
Acceptance rate: 50%
Average class size: 10 students
Application Deadline: Feb. 1 / rolling
Source: Verified school update

School News

Senior Independent Projects: On the Frontlines of Conservation - 08/06/2025
Beni 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% of private schools in New York for:

School Overview

School Membership(s)School Assoc.

National Association of Episcopal Schools (NAES)
National Association of Independent Schools (NAIS)
The Association of Boarding Schools (TABS)
New York State Association of Independent Schools (NYSAIS)

Religious Affiliation

Episcopal

Grades Offered

Grades 7-12

Offers Post-Graduate Year

Yes

ADD/ADHD Support

Yes

Learning Difference Programs

Yes

Learning Programs Supported

Dyslexia/Language Based Program for Mild Learning Differences/Executive Skills Program

Year Founded

1907

Colors

Blue, Gold

School Calendar

View School Calendar

First Day of School

Sat. Aug 30, 2025

Last Day of School

Fri. May 29, 2026

Campus Size

230

Student Body

Total Students

264 students

Student Body Type

All-boys

% Students of Color

19%

State avg.: 40%

Students by Grade

Academics and Faculty

Total Classroom Teachers

45 teachers

Student : Teacher Ratio

6:1

National avg.: 13:1

% Faculty w/Advanced Degree

65%

Average Class Size

10 students

Number of AP Courses

15 courses

List of Courses Offered

Link to List of Courses

Advanced Courses

AP BiologyAP Calculus AB/BC

AP ChemistryAP English Language

AP English LiteratureAP Environmental Science

AP MacroeconomicsAP Microeconomics

AP Music TheoryAP Physics 1

AP Physics C: MechanicsAP Statistics

AP Studio ArtAP U.S. History

Matriculation DataMatric. Data

View Matriculation Data

Classroom Dress Code

Formal

Formal School Dress, Class Dress, Informal Dress, Casual Dress

Tuition and Acceptance Rate

Admission Deadline

Feb. 1 / rolling

Yearly Tuition Cost

$76,500

View national tuition avg.

Tuition Notes

Boarding $76,500; Day Students (Grades 9-12) $54,400; Day Students (Grades 7-8) $37,000; 5-Day Boarding $65,250

% on Financial Aid

50%

Average Financial Aid Grant

$32,500

Acceptance Rate

50%

National avg.: 81%

College Acceptance Rate

100%

Admissions Director

Jeff Beck

Admissions Associate

Meredith Timone

Application URL

Online Application

Endowment Size

$55 million

Sports

Total Sports Offered

13 sports

Sports

BaseballBasketball

Cross CountryFootball

GolfIce Hockey

LacrosseMountain Biking

SoccerSquash

TennisTrack and Field

Wrestling

Extracurriculars

Total ExtracurricularsTotal Extra-curric.

51 extracurriculars

ExtracurricularsExtra-curric.

Club or Organization:

30 For 30 ClubAcolytes & Vergers

Asian SocietyBaking Club

Bridge ClubCheese Club

Chess ClubCoffee House and Tea Club

Cooking ClubDeans Advisory Council

Diversity ClubDog Walking Club

Dorm ProctorsEntrepreneurship Club

Environmental ClubFinance Club

Fishing ClubFuture Health Care Professionals Club

Global Leadership ClubHealth and Wellness Club

Key ClubKnitting Club

Model UNNational Honor Society

NewspaperOuting Club

PallbearersPolitical Forum Club

Random Acts of Kindness ClubRelay for Life

Robotics ClubSign Language Club

Spirit ClubStrategy Board Games Club

Student ActivitiesStudent Senate

Video Game Culture ClubWoodworking Club

Show More (22)Hide

Arts and Music Programs:

Anime ClubDrama Club

Jazz BandOpen Mic Club

Pottery ClubRock Band

Tech CrewTrinitones

Recreational Athletic Programs:

FarmingFutsal Club

Rock ClimbingRock Climbing Club

Strength and Conditioning Club

School Notes

School Motto: Fides Et Virtus
School Mascot: The Pride

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 theWinter Project,Global Collaborative Challenge, andSenior 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 programand individualized academic support have provided an environment where students are transformed - achieving their academic goals in ways they never expected, finding their confidence, and preparing for their futures.

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 player, Buffalo Bills

Source: Verified school update

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Frequently Asked Questions

How much does Trinity-Pawling School cost?

Trinity-Pawling School's tuition is approximately $76,500 for private students.

What is the acceptance rate of Trinity-Pawling School?

The acceptance rate of Trinity-Pawling School is 50%, which is lower than the national average of 74%.

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 13 interscholastic sports: Baseball, Basketball, Cross Country, Football, Golf, Ice Hockey, Lacrosse, Mountain Biking, Soccer, Squash, Tennis, Track and Field and Wrestling. Trinity-Pawling School is ranked as one of the top 20% of private schools in New York for most sports offered.

What is Trinity-Pawling School's ranking?

Trinity-Pawling School ranks among the top 20% of private schools in New York for: Most AP courses offered, Most sports offered, Most extracurriculars offered, Oldest founding date and Largest endowments.

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 ).

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