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

700 Route 22
Pawling, NY 12564

Trinity-Pawling School Photo #1 - Mission: Trinity-Pawling School will provide an educational experience that makes a transformational difference in the lives of its students by enabling them to discover and pursue their distinctive gifts and talents.

Trinity-Pawling School Photo #2 - 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 #3 - 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 45 years, this signature program and individualized academic support have been providing an environment where students are transformed.

Trinity-Pawling School Photo #4 - 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 #5 - 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 #6 - Open seven days a week for breakfast, lunch, and dinner, Scully Dining Hall offers a healthy variety of hot entrees, with vegetarian options, a full salad bar, homemade soups, a deli and panini station, and a homemade dessert bar. As a school, we are committed to wholesome, nutritious meal preparation, food safety, and sustainability.

Trinity-Pawling School Photo #7 - The Effort System is Trinity-Pawling`s distinct approach to inspiring and measuring student growth. It assesses students in multiple dimensions: academics, dorm life, athletics, work program, and extracurricular involvement. Through this ethos of effort, we challenge young men to become ambitious, well-rounded individuals in all aspects of life.

Trinity-Pawling School Photo #8 - Through an array of theater courses and extracurriculars, the Trinity-Pawling Theater Department ignites passion in our students, in all aspects of the theater arts - whether acting, improvisation, directing, playwriting, producing, or lighting and set design.

Trinity-Pawling School Photo #9 - 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 #10 - 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 offers an individualized educational experience to 275 boys in grades 7-12 and postgraduates.

The School delivers entrepreneurial and ambitious programs that provide its students with opportunities for teamwork and camaraderie, independent exploration, and the discovery of their gifts and talents.

With over 100 academic courses, 17 Advanced Placement courses, 13 athletic teams competing in the New England Founders League (one of the oldest and most competitive athletic leagues in the country), and a multitude of extracurricular activities, our students have many opportunities to reimagine and own their education.

In addition to building a foundation of character and self-awareness in its students, the School teaches boys to be creative, compassionate, and collaborative.

Driven by both personal integrity and public purpose, students are prepared to contribute positively as leaders and citizens in their local, national, and global communities.

Quick Stats (2025)

Top Ranked NY School
Grades: 7-12
Enrollment: 293 students
Yearly Tuition: $71,000
Acceptance rate: 50%
Average class size: 10 students
Application Deadline: None / Rolling
Source: Verified school update

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)
State or regional independent school association
The Association of Boarding Schools (TABS)

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

School Calendar

Link to School Calendar

Student Body

Total Students

293 students

Student Body Type

All-boys

% Students of Color

21%

State avg.: 39%

Students by Grade

Academics and Faculty

Total Classroom Teachers

50 teachers

Student : Teacher Ratio

6:1

National avg.: 13:1

% Faculty w/Advanced Degree

65%

Average Class Size

10 students

Number of AP Courses

17 courses

List of Courses Offered

Link to List of Courses

Advanced Courses

Advanced App Development, AP American History, AP Art History, AP Biology, AP Calculus AB/BC, AP Chemistry, AP Computer Science A, AP English Language, AP English Literature, AP Environmental Science, AP Macroeconomics, AP Microeconomics, AP Music Theory, AP Physics 1, AP Physics 2, AP Physics C: Mechanics, AP Statistics, AP Studio Art

Matriculation DataMatric. Data

Link to Matriculation Data

Classroom Dress Code

Formal

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

Tuition and Acceptance Rate

Admission Deadline

None / Rolling

Yearly Tuition Cost

$71,000

View national tuition avg.

Tuition Notes

Boarding $71,000 Day (9-12) $50,500 $56,250 5-Day Boarder

% on Financial Aid

50%

Average Financial Aid Grant

$32,500

Acceptance Rate

50%

National avg.: 85%

Admissions Director

Jeff Beck

Admissions Associate

Meredith Timone

Endowment Size

$55 million

Sports

Total Sports Offered

13 sports

Sports

Baseball, Basketball, Cross Country, Football, Golf, Ice Hockey, Lacrosse, Mountain Biking, Soccer, Squash, Tennis, Track and Field, Wrestling

Extracurriculars

Total ExtracurricularsTotal Extra-curric.

55 extracurriculars

ExtracurricularsExtra-curric.

Club or Organization:
30 For 30 Club, Acolytes & Vergers, Africana Club, Allies(LGBTQ), Amen Boys, Asian Society, Baking Club, Bridge Club, Cheese Club, Chess Club, Coffee House and Tea Club, Cooking Club, Cribbage Club, Deans Advisory Council, Diversity Club, Dog Walking Club, Dorm Proctors, Entrepreneurship Club, Environmental Club, Finance Club, Fishing Club, Future Health Care Professionals Club, Global Leadership Club, Health and Wellness Club, Key Club, Knitting Club, Model UN, National Honor Society, Newspaper, Outing Club, Pallbearers, Political Forum Club, Random Acts of Kindness Club, Relay for Life, Robotics Club, Sign Language Club, Spirit Club, Strategy Board Games Club, Student Activities, Student Senate, Video Game Culture Club, Woodworking Club

Arts and Music Programs:
Anime Club, Drama Club, Jazz Band, Open Mic Club, Pottery Club, Rock Band, Tech Crew, Trinitones

Recreational Athletic Programs:
Farming, Futsal Club, Rock Climbing, Rock Climbing Club, Strength and Conditioning Club

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 an individualized 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 gifts and talents. With over 100 academic courses, 17 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.
The School's Center for Learning Achievement recognizes the potential in each and every student and offers programs that are tailored to students who have dyslexia and language-based learning differences. For over 45 years, this signature program and 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

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 $71,000 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 79%. Trinity-Pawling School's acceptance rate is ranked among the top private schools in New York with low acceptance rates.

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 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: Lowest average acceptance rates, Most AP courses offered, Most sports offered, Most extracurriculars offered and Oldest founding date.

When is the application deadline for Trinity-Pawling School?

The application deadline for Trinity-Pawling School is rolling (applications are reviewed as they are received year-round).

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