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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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Phillips Academy (Andover)
Phillips Academy, commonly known as Andover, was founded in 1778 by Samuel Phillips Jr., making it one of the oldest incorporated schools in the United States, predating even the country's own founding as an independent nation by a matter of months. The school's history includes a notably early commitment to expanding access, and its alumni include two U.S. presidents from the same family, George H.W. Bush and George W. Bush, alongside numerous other prominent figures across politics, business, and the arts. Andover's extensive campus includes its own archaeological museum, art museum, and observatory, reflecting an unusually resource-rich institutional history built up over nearly two and a half centuries of continuous operation and alumni philanthropy. Phillips Academy's combination of its status as one of the nation's oldest schools and its multi-generational presidential and prominent alumni lineage has made it one of the most historically significant boarding schools in the country.
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