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Maeder was born in Hamburg, Germany on December 29, 1909, the third child in a prosperous family. He described his father as an authoritarian nationalist and anti-Semite who embraced Hitler's message. Maeder left home at 18, refusing to go into business as his father had had wished, and deciding instead to become a teacher.
Maeder was released from an internment camp in Texas on February 23, 1943. Arriving in New York, Maeder soon obtained a position as the director of the boys' division of a YMCA in Williamsburg, Brooklyn.[5] In September 1944, Maeder took a teaching job for a year at Windsor Mountain School in Lenox, Massachusetts, several miles from the site of the future Stockbridge School.
Maeder then moved to the Walden School, a private day school in Manhattan, teaching German and the history of languages and briefly serving as the school's director in 1947 and 1948. It was at Walden that he met his wife Ruth, a widow at the time, through her son David, a Walden student whom he later adopted. Maeder left Walden in 1948 to found Stockbridge School.
The Maeders paid $60,000 to acquire the 1,100-plus acres of the former estate of Daniel Rhodes Hanna, son of Mark Hanna. Their purchase of what became the site of Stockbridge School occurred shortly after the failure of Liberal Arts, Inc. to establish a Great Books-based college associated with St. John's College, Annapolis, Maryland, on the same site. The property had been vacant since the Great Depression and extended from the summit of West Stockbridge Mountain to the shore of a lake called the Stockbridge Bowl. Only a portion of this extensive property became the school campus, with the Maeders retaining title to the remainder.
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