In 1916, Francis Behn Riggs purchased land and buildings on the site of the present Upper Campus. Educated at Groton and Harvard, Riggs originally founded an agricultural high school for boys, named the Riggs School. Indian Mountain School assumed its current name in 1922 when it became a boarding school designed to prepare boys for the entrance examinations of secondary boarding schools. 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. Indian Mountain School enrolled eight boys that first year ranging in age from eight to 14.
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 current motto, life through service was adopted from the original 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. In November 1928 the main school building was destroyed by fire but Riggs was able to raise the funds to construct the current brick building 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 as a 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 40 students and their instructors, was full that fall.
Riggs retired in June 1939, after 23 years at the school, and William M. Doolittle became the school’s second headmaster. Through the depression, numbers had dwindled and Mr. Doolittle began the year with only 18 boys enrolled, but the situation improved steadily. For the first time, day students were accepted, and in 1941 girls were also accepted as day students. In 1942, Mr. Doolittle took 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 returned and began a 14-year program of building and expansion. The enrollment that year was evenly split between day and boarding students. For eight of those 14 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. By 1969, a new classroom wing, auditorium/gymnasium, dining hall, and dormitory had been added to the original structure to accommodate the increasing population. Mr. Doolittle and his wife, Constance, who had served the school as a teacher since 1941 and as co-head since 1967, retired in July 1970.
Richard W. Rouse succeeded Mr. Doolittle and moved into the newly constructed headmaster’s residence. During his seven years as head, Doolittle Dormitory was built and dedicated, and 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. 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 and constructed an Adventure Education facility on Indian Mountain, but saw a decline 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. 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 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 playing field for girls.
On July 1, 2003, Indian Mountain School merged with the neighboring pre-kindergarten through fourth grade school, formerly known as The Town Hill School.
The Town Hill School began in the 1930s 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. The school opened that first year with an enrollment of 22 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. A pre-kindergarten was established for the 1987-1988 school year.
Following Connie Garrity’s retirement in 1978, the school had a series of short-lived heads of school until Judy Boynton became Head of School in 1992. 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. Judy Boynton resigned in 1997.
The school moved to its present 12-acre campus in August of 1998. Subsequent to Judy Boynton’s departure, there was another period of turnover in the heads of school until the merger with Indian Mountain was agreed in 2003. In 2004, Trish Hochstetter, became the Lower School Head, while continuing her role as the Learning Skills Specialist on the Lower Campus until she resigned in 2014. Rebekah Jordan is now the Head of the Lower School.
In July 2006, Mark A. Devey became Indian Mountain’s eighth Head of School. Under Mr Devey’s leadership, enrollment stabilized, the curriculum was further refined, and the school launched a $7 million capital campaign to finance the construction of a new dormitory building with additional faculty housing, (completed in 2012) and a new Student Center (completed in January 2014) as well as to add to the school’s endowment.