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Groton School
Groton School was founded in 1884 by Endicott Peabody, an Episcopal clergyman who modeled the school partly on English boarding school traditions and led it as headmaster for over half a century, embedding a strong emphasis on religious and moral education alongside academics. The school's most notable alumnus is President Franklin D. Roosevelt, who attended Groton before Harvard, and Peabody personally maintained a close relationship with Roosevelt throughout his life, including officiating at both of Roosevelt's weddings and later corresponding with him during his presidency. Groton's historically small enrollment, deliberately kept much smaller than many peer boarding schools, reflected Peabody's specific educational philosophy prioritizing close faculty-student relationships and a tightly knit community over institutional scale. Groton School's combination of its founder's deeply personal, multi-decade relationship with a future U.S. president and its deliberately intimate small-school philosophy has made it one of the most historically distinctive boarding schools in the country.
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Deerfield Academy
Deerfield Academy was founded in 1797 in the historic Connecticut River Valley town of Deerfield, Massachusetts, and it underwent a dramatic transformation during the multi-decade tenure of headmaster Frank Boyden, who led the school from 1902 to 1968 and built it from a struggling local academy into a nationally prominent institution. Boyden's unusually long tenure, one of the longest headmasterships of any major American secondary school, let him personally shape Deerfield's academic culture, campus development, and admissions strategy across nearly seven decades, a level of sustained single-leader influence rare in American education. The school's setting within the historic Deerfield village, itself a nationally recognized historic district featuring preserved 18th- and 19th-century architecture, gives the campus an unusually direct physical connection to early American colonial history. Deerfield Academy's combination of Frank Boyden's historically singular multi-decade leadership and its setting within a nationally significant historic village has made it one of the most distinctively rooted boarding schools in the country.
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