Trinity-Pawling School (formerly The Pawling School) is an independent, college-preparatory boarding school for boys in grades 7-12 and postgraduates, located in Pawling, New York, United States. The school, located on a 230-acre campus in southern Dutchess County, is located 60 miles north of New York City.

Trinity-Pawling School was founded in 1907 by Frederick Luther Gamage, previously headmaster of St. Paul's School. The first school building was Dutcher House, which had previously functioned as a hotel. Shortly after, George Bywater Cluett, who had previously donated money to Gamage for a gymnasium at St. Paul's, provided a larger grant for a new flagship building for the school that was then known as The Pawling School. In 1910, it moved to its present location on Route 22, in a new building designed by New York City architect Grosvenor Atterbury, named Cluett Hall. The Pawling School was renamed Trinity-Pawling School in 1947. One of Trinity-Pawling's first students was William Bradford Turner, a descendant of the first Massachusetts Bay Colony Governor William Bradford. Turner was killed in action in World War I and was posthumously awarded the Medal of Honor.

The school offers the following AP classes:

The school has 13 varsity sports competing against Founders League and non-league foes. The Founders League comprises Trinity-Pawling School, Kent, Taft, Avon, Hotchkiss, Choate, Kingswood-Oxford, Loomis Chaffee, and Westminster. Girls' schools in the league are Ethel Walker and Miss Porter's.

In the fall, the school offers boys football, soccer, mountain biking, and cross country. The school provides wrestling, squash, hockey, and basketball in the winter. In the spring, teams compete in track and field, baseball, tennis, golf, and lacrosse. There are lower-level teams for all of these sports, which routinely send players up to the varsity level.

Facilities include the Smith Field House and a new turf field lined for soccer, football, and lacrosse. The field was dedicated to long-time football coach, former Associate Headmaster, and Director of Studies David N. Coratti in the fall of 2013. Additionally, nine new tennis courts were completed in 2013. Tirrell Rink was renovated in 2010. Facility updates and additions were provided by the generosity of Trinity-Pawling alums.

The school offers six soccer fields, a basketball court (Hubbard Court), a cardio room, and a weight room. The Rock Squash Courts opened in 1999, and the McGraw Wrestling Pavilion opened in 1998. The baseball field was renovated and named for Mo Vaughn, Class of 1986. An all-weather track was installed in 2006, and a grass football field remains on the west side of Route 22.

At Trinity-Pawling, all the arts are under one roof. The Gardiner Arts Center was formerly the school's gym from 1911 to 1960 and was used as an auditorium until 2002.

There are 50+ clubs and extracurricular activities offered to students each year. Some mainstays are Model UN, Diversity Club, Debate Club, Theater Tech Crew, Key Club (Admissions tour guides), and Film Club. Each student must participate in a club, program, or activity during their time at Trinity-Pawling.

The Honor Council is a student organization. Members are elected to the Honor Council by their peers and are responsible for upholding the Honor Code through personal example while educating the student body in honorable behavior. An honor pledge is signed by all students and faculty at the beginning of each academic year as follows:

"Honesty and integrity live at the heart of the school. Behavior inspired by faith and virtue creates honor in the academic community and allows us to live by the principles of the Trinity-Pawling Honor Code: My efforts, preparations, and presentation are at all times honest."

1. Each year, the student body and faculty vote to name five to seven prefects to lead the student body. They are announced at the Stepping Up Ceremony, the school's internal graduation, the day before Commencement.
2. Dress Code: For Chapel, the boys dress in "Blues and Grays", consisting of a blue blazer, gray pants, white shirts, and usually a blue and gold tie. Recently, the boys have adopted the bow tie as a go-to for these events and often regular class days. Class Dress is a blazer, tie, and traditional khaki-style pants with shoes. Usually, once a term, there will be a dress-down day to raise money for a charity or special cause. Neat Informal consists of a collared shirt with traditional khaki-style pants.
3. Thanksgiving Dinner occurs the night before the last exam before the break. Each faculty table enjoys a turkey dinner with all the fixings. The prefects judge the best faculty carving performance and give several other humorous awards.
4. Candlelight is the special Christmas/holiday celebration held on two occasions: one for the Pawling community and the other for the students, faculty, and their families. A roast beef dinner follows this.
5. Head of School Holidays occur once per term. They allow the boys a night free of homework and the ability to sleep in the next day. Sports practices and evening study hall take place to conclude the day.

School Prayer

"O Spirit of Life, Wonderful Counselor: Let your presence in our midst make this school a fountain of wholesome activity and true knowledge: to her Trustees grant timely wisdom, to her Teachers the gift of inspiration, and to her Students a questing spirit; that soundness of learning, loftiness of character, and a capacity for gallant living may be furthered in this place from generation to generation; through Jesus Christ our Lord. Amen."

Alma Mater

Pawling, hear thy sons who love thee
Sing in worthy praise.
Pledging to our Alma Mater
Loyal hearts always.
Faith and courage, thy foundations,
Spread a-far thy fame:
We revere thee, Alma Mater
Honor'd be thy name.

Green the fields on which we triumphed:
Strong the friendships made.
Sunset o’er the western hillsides;
Pond in which we played.
Blazer, tie, crest worn with honor,
Boys now and always.
Chapel bells rang out the hours,
Cherish we those days.

Those who go from out thy portals,
Hallowed mem’ries bear,
Of the days of earnest striving
For thy glory there.
Here we gather strong in spirit
Singing joyfully,
Ever steadfast in devotion,
Pawling hail to thee!

School Hymn

For all the saints, who from their labors rest,
Who thee by faith, before the world confessed,
Thy Name, O Jesus, be forever blessed.
Alleluia, alleluia.

Thou wast their rock, their fortress, and their might:
Thou, Lord, their Captain in the well fought fight;
Thou, in the darkness drear, the one true Light.
Alleluia, alleluia.

O may thy soldiers, faithful, true, and bold,
Fight as the saints, who nobly fought of old,
And win, with them, the victor's crown of gold.
Alleluia, alleluia.

• Grieg Taber

• Official website
• The Association of Boarding Schools profile