The Hillside

Home Our History

Our History

At South Kent School we proudly celebrate our rich 100 year history that has shaped our institution and acts as a guiding light for our future. From modest beginnings in 1923, South Kent has evolved into a distinguished educational establishment that remains true to its core values while embracing a modern world.  Located 1.5 hours from New York City on 650 acres in Litchfield County, South Kent is comprised of Kent natives, northeast families and international students alike.

Top All-Boys School in New England

South Kent School has consistently earned recognition for its commitment to excellence and dedication to providing an outstanding education for young men. According to various reputable sources, including NicheUS NewsGreatSchools | Wikipedia

Accolades Include:

  • Best All-Boys School in New England
  • Best All-Boys School in Connecticut
  • Best Episcopalian Boys School in Connecticut
  • Best All-Boys School for Soccer/Basketball/Ice Hockey
  • Best All-Boys School with Mountain Biking
  • Best Small Private Boys’ School in New England
  • Best All-Boys School with Robotics
  • Best Private School for Boys in Connecticut
  • Top-Ranked All-Boys School in Connecticut

These accolades are a testament to the school’s unwavering commitment to providing a top-notch education, fostering character development, and excelling in various fields.

Simplicity, Self-Reliance, Directness of Purpose

Founded as a collaborative effort between Father F. H. Sill, Samuel Slater Bartlett and Richard M. Cuyler, South Kent School emerged with a mission deeply rooted in providing a holistic education for boys of ability, character, and as an elite yet affordable school for families with limited means. The original purpose emphasized the cultivation of simplicity, self-reliance, and directness in the boys’ lives that instilled leadership, accountability, and high academic standards.

Academics, Work, and Service

Life for South Kent boys in the early years was a rigorous blend of church activities, academics, work responsibilities, and athletic pursuits. Boys actively participated in the development of the school, from building the chapel to harvesting crops on the extensive farmland. Under the compassionate yet watchful eye of Sam Bartlett, the “Old Man,” South Kent thrived despite the hard challenges of the Depression era.

Post-War Transition

The post-war years brought both prosperity and transition to South Kent School. Sam Bartlett, retired after thirty-three years of devoted service, handing the reins to L. Wynne Wister in 1954. Under Mr. Wister’s leadership, the school expanded with new buildings, including a library and science center. The headmaster’s role continued to embody the spirit of a father figure to the South Kent family.  Following Wister’s fourteen years of service a key founder, Sam Barlett’s son, George Bartlett became the Head of School maintaining and renovating the traditions that had evolved uniquely at South Kent. Traditions include a balance of academic excellence, service in the community, and athletic engagement.  During Barlett’s tenure, the school embarked on a major capital campaign, resulting in the construction of the Joseph J. Brown Gymnasium and the Richard M. Cuyler Hockey Rink.  The establishment of top-notch sports facilities propelled South Kent School into a prominent position within NEPSAC schools, ultimately solidifying its status as a national powerhouse in Basketball, Soccer, and Hockey.

South Kent School Basketball won the NEPSAC Championship in 2023, and all three programs are proud have had notable athletes embrace successful professional careers.  To date, there are 410 number of South Kent students who have gone on to play in college and 42 at the professional ranks.


Subsequent headmasters, including Pedro Arango, Noble Richards, and John S. Farber, each brought their unique contributions to the South Kent legacy. The school weathered economic challenges, but with that has continued to expand its campus and programming with support from alumni and friends, adding to its legacy one of the best mountain biking trails in the tri-state area.  South Kent’s pristine and historic 650 acre campus naturally affords a blend of indoor and outdoor learning and a focus on environmental sciences.

Embracing the Future

As South Kent School enters its 100th year, the institution is embracing the future under the visionary leadership of Brian Sullivan, the new Head of School. Sullivan brings a modern perspective to education, launching South Kent’s marquee Futures Literacy Programs. This innovative initiative places a strong focus on real-world STEM applications, AI, technology, and entrepreneurship.

Sullivan’s commitment to preparing students for the challenges of the 21st century aligns seamlessly with South Kent’s founding principles. The school looks toward the next century with enthusiasm, building on its storied past while adapting to the evolving landscape of education.

In celebrating 100 years, South Kent School stands as a testament to the enduring power of education and the profound impact it can have on generations of students. The journey continues, and South Kent remains steadfast in its commitment to shaping young minds for the challenges and opportunities of the future.

Read below an article from our archives on the history of South Kent School by Marge Smith Curator/Archivist.  Smith is the award-winning curator of the Kent Historical Society and the Sharon Historical Society, .

Nestled within the picturesque landscapes of South Kent, Connecticut, South Kent School stands as a beacon of academic excellence and character development. Situated on a sprawling 650-acre campus in western Litchfield County, the school overlooks the scenic vistas of the former Housatonic Valley rail-line, Hatch Pond, and the historic ‘whistle-stop’ South Kent station, while Bull Mountain provides a majestic backdrop to this idyllic setting.

Founded in 1923, South Kent School epitomizes its motto of “Simplicity of life, Self-reliance, and Directness of purpose”. Since its inception, the school has been committed to providing a service-oriented education tailored to boys of ability and character, fostering self-sufficiency and a sense of responsibility in its students.

The roots of South Kent School 100 years history, traces back to the emergence of the hamlet of South Kent in the mid-1700s, a bustling center of iron production spearheaded by Jacob Bull. However, with the advent of railroads in the 1840s, the iron industry faced formidable competition from western foundries, leading to its eventual decline. By the turn of the 20th century, the area witnessed a decline in population, paving the way for the establishment of educational institutions like South Kent School.

Founded in 1923 through a collaborative effort between Reverend Frederick Herbert Sill, headmaster of Kent School, and his recent graduates Samuel Slater Bartlett and Richard M. Cuyler, South Kent School emerged as a beacon of hope in a rapidly changing world. The acquisition of the Straight farm from the Judd family marked the beginning of a transformative journey, with students actively participating in the daily operations and maintenance of the school.

Under the stewardship of its first headmaster, Sam Bartlett, South Kent School flourished, shaping the lives of countless young men over the course of 45 years. Subsequent leaders such as L. Wynne Wister, George M. Bartlett, and Noble Richards continued to uphold the school’s legacy of excellence, steering it through periods of growth and transformation.

Today, South Kent School remains steadfast in its commitment to providing a nurturing environment where students are encouraged to excel academically, develop strong moral character, and contribute meaningfully to society. Guided by an independent board of trustees and led by Head of School Brian D. Sullivan, South Kent School continues to uphold its rich heritage while embracing the challenges and opportunities of the 21st century, ensuring that its legacy of excellence endures for generations to come.

People in the quiet little hamlet of Pigtail in South Kent, Connecticut, watched with curiosity as a straggling parade of unfamiliar cars made its way up the twisty dirt road towards the brand-new South Kent School throughout the day on September 26, 1923. These neighbors had seen all the frantic activity going on over the previous four months at the old Judd farm, with some of them actually lending a helping hand with the preparations. Pigtail was about to acquire 24 new residents, from all over the country. Today was the big day.

Curiosity, along with a healthy dose of nervous apprehension, surely was felt as well by the growing cluster of young boys in knickers, who, having bid tearful goodbyes to their families, began to take in their new surroundings. Bits of building material and plumbing supplies cluttered the yard, and a new flagpole lay flat on the ground, awaiting the time when it could be placed upright and the flag hoisted. But the school building in front of them shone with a fresh coat of paint, and the barns and fields around them held the promise of many places to explore. The new grownups in their lives, Mr. Bartlett, Mr. Cuyler, Mr. Goodwin and Miss Dulon, hiding their own apprehension, greeted them warmly and began the process of settling them in.

By the boys’ own account, written several years later in the 1928 yearbook, “school started off with a bang the first night. The air in the dormitory was virtually thick with missiles of shoes, slippers and the like.” Those 24 charter scholars were Aaron, Brown, Buckingham, Colt, Cumming, deCoppett, Dingwall, Gilbert, Gustafson, Harris, Hazen, Kimball, McManus, Meyer, Murphy, Newhall, Ransom, Schurz, Stevens, Thompson, Ward, White, Whitney and Woodward, entering the Second and Third Forms. They were to be joined in January by four more boys: Balch, Gillette, Simpson and the very young 11-year-old Files, who was often quite homesick. The Second Form was the equivalent of eighth grade, with the average Second Former being 13 or 14 years old. As the school grew over the next three years, Fourth, Fifth and Sixth Forms were added, with the Sixth Form being the equivalent high school senior class.

Dinner consisted of scrambled eggs cooked by the Headmaster, and was followed by the first chapel service, held in the classroom, at which they sang, “The Son of God Goes Forth to War.” The altar was a packing box topped with a cross made of a couple of sticks, and the congregation was made up of two masters, the Housemother and three boys who knelt on the floor between the desks. The next day, instead of heading for the classrooms, the boys were given shovels and rakes, and put to work alongside the masters to help get the yard cleaned up and tidy. Part of the reason may have been that the main classroom was still full of plumbing supplies, and also the fact that there were no books to be had! But soon they all started to settle into the beginnings of routine, with classes, chores, meals, athletics and chapel. The boys were very young, however they learned very quickly that much was expected of them as integral players in getting the new school up on its feet.

Though the old farmhouse had been doubled in size, the school building was packed tight. The third floor held the dormitory, a washroom with showers and lockers, and rooms for Mr. Cuyler and Mr. Goodwin. The dorm rooms were so small that most of the boys did not have their own dresser in which to store their clothes, but there was a large one down the hall that they shared. A small, rudimentary infirmary was on the second floor, along with rooms for Miss Dulon and Mr. Bartlett. The first floor housed the dining room, classrooms, reception room, living room with a makeshift library, and finally the kitchen and other utility rooms. Eventually, space for a chapel was created in a room in the basement. The 1929 Class History spelled out the truly spartan conditions of the first few years: “Our study-hall was what is now a supply room. In the winter the temperature in this room went down to fifteen degrees above zero, and classes were held in mittens and sheepskins. The blackboard was only a large piece of card-board which soon became useless as every chalk-mark scratched off the paint.”

In the beginning, all aspects of running the school were done by the same few people. Teachers doubled as coaches, dorm masters and even business managers, while Mr. and Mrs. Martin and Miss Dulon took care of just about everything else, usually with the help of the boys. As the school grew in later decades, the workload came to be distributed over many more-focused staff positions, but at the start, the self-help system with the boys was a true necessity as well as an educational goal. There was no set job program at first, yet there was no end of work for the boys to do. Mr. Bartlett noted in his diary, “Miss Dulon has proved herself a gold mine. She is a wonder and there is nothing she cannot do. The boys and the parents think very highly of her… Stan Goodwin has without doubt proved a success. He has all the boys at his heels and his table is continually in a roar of laughter… Of course Dick is the stump to which I always tie my ship in case of storm. He is working harder than any of us.”



Skip to content