Massanutten Academy began in September of 1899 when the Virginia Classis of the Reformed Church opened the school in the residence of former US Senator H.H. Riddleberger which had been enlarged to serve as classrooms and the boy’s dormitory.
The school was operated by a Board of Trustees that consisted of fifteen members from various religious denominations. They also developed a catalog that emphasized non-sectarian Christian philosophy and was designed to “equip boys and girls for entrance into the best colleges and universities of the land.” The first graduating class, who completed courses in 1902, consisted of three boys and three girls.
Howard J. Benchoff was appointed the school’s president in 1905. This began the family’s long standing connection with the school and a wave of changes on campus. The first of these changes was a building campaign that resulted in the construction of school’s most prominent building Lantz Hall. This structure housed classrooms, dormitory space, and a gymnasium.
Benchoff also changed the makeup and mission of the school. In 1910 enrollment was limited to men after a so called “incident” with one of the girls.
Seven years later, in the midst of the First World War, the academy implemented a military program to train the boys and provide them with discipline. In 1930 the War Department granted the school its own JrROTC unit. Though the military program would come to define the school, the school would remain Massanutten Academy until 1984 when it began using the name “Massanutten Military Academy.”
During the early 20th century the school also hosted some of the first Korean students to ever attend classes in the United States. These students and others from across the country often became part of the Woodstock community. Festivals often featured marching cadets who also served as honor guards and escorts during beauty pageants. Through the 1960s the school was considered one of the most prominent in the country.
However, starting in the 1980s the student began to attract more troubled students as it became known as a place to send “bad” kids. Recently though this trend has been ending. The Academy still attracts many notable students and plays a large role in the local community though financial issues and declining enrollment continue to affect it, and other military academies across the nation.