In 1916, Francis Behn Riggs purchased land and buildings on the site of the present Upper Campus. Educated at Groton and Harvard, Mr. Riggs was deeply affected by the First World War and believed that the prevention of another such conflict lay in the eradication of urban poverty and ignorance. To this end, he opened the Riggs School, a proprietary corporation committed to the operation of an agricultural high school. This school combined a college entrance curriculum with coursework designed to instruct students in all aspects of farm management. Tuition was kept low and summer vacations were shortened so that a portion of each season was spent on the farm. Each boy was “required to earn a total of $60 per year through productive work and earned the nominal rate of from 2 cents to 10 cents per hour.”

By 1922, it was clear that Mr. Riggs’s social experiment was not a sound financial adventure. On the advice of his former headmaster at Groton, Reverend Peabody, Riggs changed the name of his school and its direction. Taking the name of the hill behind the property, Riggs opened a younger boys boarding school designed to prepare students for the entrance examinations of secondary boarding schools, most of which were individualized. Classes and dormitory space were located in a large building adjacent to and south of the present tennis courts; Hadden House served as a gymnasium and faculty housing. The boys ranged in age from eight to fourteen and received semi-tutorial instruction and the benefits of country living. Indian Mountain School enrolled eight boys that first year.

From these beginnings, Riggs gradually constructed the basis of today’s School. His curriculum was a traditional one but also included such extras as carpentry and dramatics. The motto, “Life Through Service” was adopted from the Riggs School and applied to the new Indian Mountain School. The farm continued to operate for the benefit of the school kitchen, and boys engaged in an active outdoor life. By 1928, the enrollment had reached 30 boys. Near disaster was weathered when that November the main school building burned completely. Riggs was able to raise the substantial funds to construct the present fireproof brick and cement structure in time for the opening of school in September 1929, just months ahead of the Stock Market Crash. At the same time, the school was incorporated not for profit and chartered under the laws of Connecticut to “maintain forever a school for the training and education of boys and young men.” The new building, designed for forty students and their instructors, was full that fall.

The Depression and the early war years must have been difficult ones. By the end of the decade, Riggs had decided that it was time to retire and did so in June 1939, after 23 years at the school. The trustees appointed William M. Doolittle to be the School’s second headmaster. By remarkable coincidence Mr. Doolittle had, while a young master at Salisbury School ten years earlier, followed fire trucks up Indian Mountain Road and had helped empty the contents of the burning school building.

Mr. Doolittle began the year with only 18 boys enrolled, but the situation improved steadily. For the first time, boy day students were accepted, and in 1941 girls were taken as day scholars. In 1942, Mr. Doolittle was given a leave of absence to serve in World War II. In his place, Louis H. Schutte, former headmaster of the Rumsey Hall School, served as Acting Headmaster for four years.

In 1946, Mr. Doolittle began a fourteen year program of building and expansion. The enrollment that year was evenly split between day and boarding students. For eight of those fourteen years, Doolittle oversaw the operation of the Indian View School, the first instance of girls boarding on campus. During his tenure, the younger grade levels were gradually phased out, field space was increased, the mountain was crisscrossed with ski trails and lifts, and the curriculum was expanded. At the school’s fortieth anniversary in 1962, the enrollment stood at 130 students. In 1968, a ninth grade was added, thereby arriving at the configuration of the grade levels which remained until the addition of The Town Hill School in 2003. By 1969, a new classroom wing, auditorium/gymnasium, dining hall, and dormitory had been added to the original structure to accommodate the increasing population.

Throughout this period, the purposes of the school were stated as follows:

“The purpose of Indian Mountain School is to prepare its students for leading secondary schools. Real preparation aims at both admission to secondary school and success thereafter. Thus we maintain not only high scholastic standards, but also concern ourselves with all other aspects of each student’s development. For a student must gain a respect for serious effort, good habits of day to day work, and an understanding of how to live and play happily in a group, if he is to continue successfully throughout his educational program.”

In July 1970, Mr. Doolittle and his wife, Constance, who had served the school as a teacher since 1941 and as co-Head since 1967, retired. They had spent more than 30 years at the helm. The school of 18 boys and a handful of buildings had grown to a coeducational community numbering 150 students on a sprawling country campus.

In the subsequent 34 years, Indian Mountain School experienced more than its fair share of poverty and prosperity. The enrollment rose and fell and rose again. Facilities were added, interior spaces reworked or renovated, field space increased, and the mountain became an outdoor education center. Three of the four headmasters in that period were removed from their posts amid uproar and public scrutiny. Yet the school and its mission endured.

Richard W. Rouse was first to follow Mr. Doolittle and moved into the newly constructed headmaster’s residence. During his seven years as head, Doolittle Dormitory was built and dedicated, and the enrollment remained fairly constant. His successor, Peter Carleton, oversaw the addition of a new gymnasium and Stockton dormitory, while pushing the school’s enrollment to its highest point. Moreover, during Mr. Carleton’s administration the size of the endowment increased significantly. During the subsequent administration of Mark Fish, the school reinstituted a girls' boarding program, constructed an Adventure Education facility on Indian Mountain, and dealt with a precipitous drop in both enrollment and endowment.

C. Dary Dunham was appointed in 1992. He assembled a faculty dedicated to the future of the school and the fulfillment of its mission. The enrollment increased steadily, the curriculum was reviewed and reworked, and the reputation of the school grew stronger. In 2000, the school completed the building of a new library and science wing, which significantly increased the physical size of the school. Two years later, in 2002, the school also added a new music wing and expanded the auditorium to add much needed stage and seating space. Outdoor athletic space was also increased, adding a new baseball field located beyond the new library and science wing and a new girls playing field. On July 1, 2003, Indian Mountain School experienced a major transition. The school merged with the neighboring pre-k through fourth grade school, formerly known as The Town Hill School.

The Town Hill School began in the 1930’s as Mrs. Tracy’s school, named for its founder, the wife of a Hotchkiss teacher. In 1938, a group of Hotchkiss parents and others in the community, convinced of the present and future need for a strong elementary school, founded The Town Hill School. Early benefactors provided funds for the original school building, and the Hotchkiss School donated the land. Ground was broken on June 18, 1938, and the two-room school building opened three months later. The school opened that first year with an enrollment of twenty-two children in grades one through eight. Miss Penelope Oyen was Town Hill’s first Headmistress. She was assisted by Connie Garrity, who became Headmistress in 1942 and served Town Hill until her retirement in 1978.

The original two-room, two-teacher school had eight grades, which were divided into grades one through four and grades five to eight. In 1946, Indian Mountain School and Town Hill agreed that Indian Mountain would begin offering grades five through nine, while Town Hill would concentrate on grades kindergarten through four. Town Hill attracted an increasing number of families as its reputation grew. As a result of the increased enrollment, the Board of Directors approved an expansion of the original building and two classrooms were added during the summer of 1976. A pre-kindergarten was established for the 1987-1988 school year.

Following Connie Garrity’s retirement, the school experienced a series of administrative changes. Mrs. Tameson Andrews served as Headmistress from 1981 to 1983. Mrs. Martha Hansen served the school from 1983 to 1986. Mrs. Belle Carney was the school’s headmistress after the departure of Martha Hansen for one year and was replaced by Mrs. Betsy Roak for an interim spring. Mrs. Nan Balser worked as Headmistress from 1988 to 1992 and was succeeded by Mrs. Mary King for the spring of 1992.

In 1992, Judy Boynton became the sixth Head of School. Judy worked closely with trustees, faculty, and parents to increase enrollment, balance the budget, and improve curricular continuity. Enrollment stabilized between 55 to 65 full time boys and girls. In 1995 a modular classroom was added to the original school building to accommodate the growing student body.

Judy Boynton resigned as Head of School at the end of the 1996-1997 school year. Richard K. Brown, a Town Hill parent and trustee, served as interim Head for the 1997-1998 school year. William Osier took over as Head of School in June of 1998 and served the school until 2002. Nancy Elting served the school for one year as an interim Head. Abbey Newlin was hired during that year, and began her work as Lower School Head in the fall of 2003.

During William Osier’s time at Town Hill the school moved to its present campus. In September 1997, ground was broken on the twelve-acre site. The school moved to its new campus in August of 1998.

In 2002, the trustees of The Town Hill School introduced the subject of a merger to the trustees of Indian Mountain School. The merger was approved and became official on July 1, 2003. We now exist as Indian Mountain School with two campuses and serve students in grades pre-k through nine.

Since the merger in 2003, Abbey Newlin departed the school and was replaced by Trish Hochstetter. Trish was formerly the Learning Skills Specialist on the Lower Campus. She continues to serve in that capacity, while working as the Lower School Head. In July 2006, Mark Devey became Indian Mountain’s eighth Head of School. He immediately oversaw the expansion of the girls’ dormitory, pushed for the addition of new technology to the math and science departments, and introduced a new film project titled, “IndiMountain Films.” The school maintains its commitment to serving children in a supportive and nurturing environment.