Celebrating 125 Years

Pomfret was meant to be different.

We were innovators from the outset. Outliers since the very beginning. Never satisfied. Never finished. It hasn't always been easy. The path hasn't always been clear. But we've always known who we are. Our history is an unbroken line, connecting us, reminding us, that each setback is an opportunity, each challenge, an invitation — to see things differently. Pomfret is hard to describe, but easy to feel. And while some may see a school, we see an attitude — a great big way of thinking and living. Because schools don't change the world, people do.

The Wabbaquasset Purchase » 1686–1893

For thousands of years, the vast stretch of lushly wooded, rolling hills we now call Pomfret was home to two Native American tribes, the Nipmucks and the Narragansetts, who claimed opposite sides of the Quinebaug River. They called the valley Mashamoquet, or "at the great fishing place."

Eventually these two groups were succeeded by the Pequots, and in 1684, the Sachem Owaneco gave Major James Fitch a title to the area. Two years later, in 1686, Fitch sold 15,000 acres, encompassing the entirety of modern day Pomfret School, to twelve settlers for thirty pounds. Forty families soon joined the original twelve settlers, and, in 1713, the area was incorporated by the General Court of Connecticut under the name Pomfret, named after an English manor, presided over by the Lord of Pomfret. For the next 181 years, descendants of those first families added homes, farms, and inns to the top of Pomfret Hill, setting the stage for the arrival of a charismatic teacher looking for a place to start a school of his own.

The Founding » 1894–1897

William E. Peck was a member of the faculty at St. Mark’s in Southborough, MA, for 23 years. By the time his more progressive tendencies came into conflict with the school, he had risen all the way to the role of headmaster. Rather than submit, he resigned. With his wife, Harriet, he purchased the Charles Grosvenor Inn; and on October 3, 1894, Pomfret School was born.

Peck’s personal reputation and charisma, as well as his ability to engender confidence, contributed to the success of the new undertaking from the very start. By the beginning of the 1896–1897 school year, Pomfret had doubled in size, growing from 42 to 80 students and from 6 to 11 faculty members. During those early years, the Pecks lived in one of the cottages attached to the inn. A single building (the first “main house”) housed the dormitory, classrooms, and dining hall, and a nearby stable served as the first gymnasium.

Tragically, during the winter of that year, an epidemic of bronchitis and pneumonia struck the school. Peck caught a particularly virulent strain of the disease, possibly from a sick young student who he had carried in his arms to the infirmary. He died on January 7, 1897. His death marked the end of the first, short era in Pomfret’s history.

Period of Growth » 1897–1929

William “Bull” Olmsted served as Pomfret’s headmaster from 1897 until his death in 1929, making him the longest serving headmaster in Pomfret history. During his 32 years, he presided over the acquisition and creation of no fewer than a dozen landmark buildings, as well as hundreds of acres of land.

In 1905, the school hired Ernest Flagg, architect of the US Naval Academy, to draft a master plan. Over the next 10 years, Flagg would go on to design and build most of the campus core, including the School Building, the Bricks, Pyne Infirmary, Clark Memorial Chapel, and Lewis Gymnasium.

In those interceding decades, Pomfret grew not only in terms of bricks and mortar, but also in terms of enrollment and endowment. It was also a time of great athletic prowess with successful football, baseball, and ice hockey teams. Mr. Olmsted was on the field every day, and demanded the same rigorous approach to athletics that he did to academics.

On October 24, 1929, a date that would come to be known as “Black Thursday,” the stock market crashed, creating a decade-long depression that affected most of Pomfret’s families. Later that year, Mr. Olmsted died and was buried in the crypt beneath Clark Memorial Chapel. At the time of his death, he and the school had attained such stature that his obituary was published in Time magazine.

Hard Times » 1930–1951

Halleck Lefferts was the third headmaster of Pomfret School. Educated at Yale, he came from the Thacher School in Ojai, California, just as Pomfret was beginning to feel the full impact of the Depression. In 1931, the School’s treasurer announced that Pomfret would likely operate at a loss. By 1934, many families could no longer afford to send their sons away to boarding school, leading to a pronounced decline in enrollment.

Despite the financial troubles of the 1930s, the school continued to move forward. It was during this difficult time that biology, chemistry, and drawing were added to the curriculum; basketball and crew were added to the athletic program; and the faculty advisor-advisee system, which continues to this day, was introduced. With the war looming, Lefferts resigned in June of 1942 to fight with the Army, and was replaced by Dexter Strong, who had also taught at Thacher.

With Strong at the helm, the school purchased the Ben Grosvenor Inn, adding 289 acres to the campus, including a magnificent well, which remains the source of the school’s water to this day. Due in large part to the creation of a regional scholarship program, enrollment soared during this period of time. In the fall of 1948, the school opened with 151 students, the largest enrollment in its history. They came from 11 states, the District of Columbia, 1 territory, and 4 foreign countries. Under the guidance of Lefferts and Strong, Pomfret had successfully weathered two of the most difficult periods of the twentieth century, the Great Depression and World War II.

Faces of Change » 1951–1973

In the fall of 1951, David Twichell took the reins as Pomfret’s newest headmaster, and continued to guide the school — often through uncharted territory — for the next decade. Writing in the New York Herald Tribune in 1956, Al Laney penned a glowing review of Pomfret. Of the transitional, innovative character of Mr. Twichell’s tenure, he wrote: “Pomfret is surely unique in its headmaster, for there is hardly another such as David Cushman Twichell, who has quite unusual ideas and has done quite unusual things in his five–or six–year headmastership.”

Another product of Thacher School, Mr. Twichell was an idealist in every sense of the word. He believed in his students, trusted his students, and felt that the School would be better if it were more flexible, rather than less flexible. Under his leadership, two new buildings opened: the current Main House in 1956 and the Monell Science Building in 1958. By the time he resigned in April of 1961, Twichell had transformed Pomfret into one of the most progressive boarding schools in the country.

In the fall of 1961, just as the Vietnam War was heating up, Joseph Milnor became Pomfret’s sixth headmaster. Three years later, in 1964, one of the most significant events in Pomfret history would occur when John Irick, a charismatic high school student from Orangeburg, South Carolina, arrived at Pomfret for his senior year. He would go on to become the first African-American to graduate from Pomfret.

Four years later, in February of 1968, The Pontefract bannered the news that “to the joy of most, and the unhappiness of a few,” the Board of Directors had voted to admit female day students beginning the following fall. In the spring of 1973, Milnor retired from Pomfret School, leaving an indelible mark on the social fabric and political consciousness of the School.

Promise to Posterity » 1973–1979

As the 1970s wore on, financial trouble returned to the Hilltop. It would fall to 34-year-old Kenneth Deitch, an assistant professor of economics from Harvard, to guide the school through its darkest days. Deitch quickly set to work, raising money and cutting costs wherever he could, including a freeze on faculty salaries. It made him the enemy of many, but probably saved the school.
Besides the budget, Deitch also ran into opposition when he rejected the recommendations of the Curriculum Committee’s final report, which had been developed but not implemented toward the end of Milnor era. After three tumultuous but critically important years, Deitch left Pomfret in 1976.

That spring marked a turning point. Still struggling through the worst financial crisis in 80 years, Pomfret turned to Assistant Headmaster Per-Jan Ranhoff for temporary stability. For the next six months, Ranhoff guided the school while the search committee looked for a new headmaster.

Almost immediately, they landed on the Reverend Burton A. MacLean. Over the next several years, MacLean offered a steady hand as the school slowly but surely turned itself around. In 1977, the key to the school’s financial recovery finally arrived. Called the Promise to Posterity, the $2.5 million fundraising campaign aimed to improve the physical plant, erase the School’s debts, and bolster the endowment. By the end of 1979, MacLean (ably assisted by Ranhoff) had succeeded. The Pomfret community would finally be able to breathe a sigh of relief, as the turbulent times of the 1970s became an increasingly distant memory.

The Spirit of Pomfret » 1979–1989

Pomfret is known for its strong sense of community, and no one deserves more credit for cultivating that sense of community than Gerrit Keator and his wife, Marnie, who arrived on the Hilltop in 1979. “Both Gerrit and I felt that a boarding school should have a warm, happy, and loving atmosphere,” Mrs. Keator said. “Therefore, I felt that my role was to be primarily an extension of my role in my own family, i.e., Chairman of the Tender Loving Care Department.”

Under the Keator family’s charismatic leadership, enrollment continued to rise. In 1980, the School opened its doors with 297 students (232 borders and 65 day students), the most ever. When questioned, most students felt the school had improved dramatically. In general, there was better communication and more friendship between students and faculty, even as the level of academic rigor continued to rise.

The mid-1980s also marked the introduction of two important changes to campus life. First, Keator made chapel mandatory, restoring a sense of spiritual heritage to the School. Second, he began offering teachers the funds to further their education, going so far as to offer a full-year paid sabbatical to veteran teachers.

By the time Keator entered his final year as headmaster, morale was at an all-time high and Pomfret had regained its reputation as one of the best, small independent schools in the country. “Lately I’ve noticed something about our school and everyone here,” said senior Cara Landi in 1989. “A spirit seems to be surging throughout our campus. Think about how lucky we are to be here.”

Breaking New Ground » 1989–2011

When asked why he accepted the headmaster position at Pomfret, Patrick Bassett gave three reasons: the sylvan splendor of its location; its commitment to students’ intellect, creative spirit, and athletic nature; and the feeling of friendliness and happiness he felt visiting the school.


As it turned out, his greatest and most lasting achievement would have less to do with what attracted him to Pomfret and more to do with what he felt could be improved. Not long after his arrival, Bassett quickly appointed the school’s first Dean of Women “to be an instigator for raising the consciousness of women's issues.” Around the same time, he authorized the formation of a chapter of the Council for Women in Independent Schools, with the expressed intent of furthering the development of the females who studied, lived, and worked at Pomfret.

In the winter of 1992, Bradford Hastings ’68 was appointed Pomfret’s eleventh headmaster. Perhaps no headmaster since Olmsted has so fully transformed the Hilltop. A graduate of the Class of 1968, he had previously served on the faculty as a history teacher, director of athletics, and assistant director of admissions. “I want the school to increase its confidence in itself,” he said. “We should dare to do things it never tried... not just go along.”

During his nearly two-decade run, Hastings oversaw the construction of a myriad of buildings, including Centennial Academic and Arts Center, Corzine Athletic Center, Olmsted Student Union, Blodgett Boathouse, Lasell Alumni House, Jahn Rink, Blodgett Tennis Center, and Olmsted Observatory. The campus and the community would never be the same. Another major improvement was the establishment of a new central power plant, which greatly reduced the School's carbon emissions, while saving thousands of dollars in annual fuel costs. By the end of his long tenure — the second longest in school history — he had safely steered the school into the 21st century.

The Pomfret Purpose » 2011–

In 2011, J. Timothy Richards, a graduate of Phillips Andover and a long-time faculty member at St. George’s School, took the reins as Pomfret’s twelfth headmaster. Richards' arrival has heralded a new approach to teaching and learning at Pomfret. “If the next generation is to flourish in a changing world," he says, "we must prepare them wisely, differently, and well."

In 2013, the School launched its vision for the future: The Pomfret Purpose. Among the four goals outlined in the strategic plan, the school has set out to become a leader in learning, and to create a truly distinctive boarding school experience.

Through the generosity of Peter and Laurie Grauer, Pomfret's Board of Trustees approved the creation of an endowed fund to establish and support the Grauer Family Institute for Excellence in Education, which inspired the School to reimagine its daily schedule, academic offerings, and teaching methodologies.

Seven years into his tenure, Richards acknowledges that change is hard, but embraces the idea that education must continue to evolve to meet the needs of a new age. “We are dedicated to preparing our students with the knowledge, skills, and character they will need to thrive in the 21st century,” he says.

Yet, while change beckons, the school remains grounded in tradition. A growing body of research confirms that our small student population, our commitment to knowing every student well, and our careful cultivation of an inclusive and intellectually curious community are the hallmarks of a transformational boarding school experience.

Together, these twin forces of tradition and innovation are the cornerstones of the next era in Pomfret’s history.