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The 10 Most Legendary Prep Schools in America

While many students set their sights on top colleges by toiling away at public schools, a select few are able to afford the luxury of studying at highly exclusive prep schools. Many of these schools were established as feeders for renowned universities like Harvard, Yale, and Stanford, and are designed with the express goal of high-level college in mind. Often, the students at these schools are the sons and daughters of government figures, celebrities, business magnates, and even royalty. Many go on to fill these types of roles themselves. Naturally, there is a major air of prestige, history, and even legendary status when it comes to these schools. We’ve highlighted 10 of the most legendary of college prep schools, full of history, famous alumni, and even a few interesting stories.

  1. Phillips Exeter Academy

    Founded in 1781 as a feeder school to Harvard University, Phillips Exeter Academy is considered to be one of the most prestigious prep schools in existence. Exeter has, hands down, one of the largest endowments of any U.S. prep school at $1 billion. The school boasts the largest secondary school library in the world with 160,000 volumes on nine levels and is recognized as one of the Masterworks of Modern American Architecture. Alumni of Exeter include U.S. Presidents, Secretaries of State, members of Congress, Attorney Generals, notable writers, business figures, and celebrated artists, including Mark Zuckerberg, John Irving, Gore Vidal, and members of the Rockefeller family.

  2. Phillips Academy

    Commonly referred to as Andover, Phillips Academy was founded by Samuel Phillips Jr., the nephew of Phillips Exeter founder John Phillips. Andover was established just three years prior to Exeter, and the two schools have enjoyed an intense rivalry from the beginning. The academy established a pedigree of excellence early on: Paul Revere himself designed the school’s seal, and upon visiting the campus, George Washington was so impressed that he encouraged his nephews to attend (and they did). The school’s articles of incorporation boast the signature of John Hancock. The Andover campus is home to not one, but two museums featuring major works; The Addison Gallery of American Art boasts more than 16,000 works in all media, and the Robert S. Peabody Museum of Archaeology is one of the foremost Native American archaeological collections. Andover has educated two American Presidents — both George H.W. Bush and George W. Bush — as well as inventor Sam Morse and actor Humphrey Bogart (who was expelled). Graduates of Andover typically matriculate to top-tier colleges including Yale, Stanford, Harvard, and Columbia, as the school was originally set up to send its students to Yale. Like Yale, Andover has secret societies, although officially, they were terminated in the 1940s.

  3. Trinity School

    Considered to be one of, if not the, best college prep schools in the U.S., Trinity School is renowned for its excellent academic reputation. It is the oldest continually operated school in New York City, and the fifth oldest in the U.S. Trinity has traditionally educated its students for Columbia University, and still does, but students go on to other exclusive colleges, including the Ivy League, MIT, and Stanford, with Trinity boasting an incredible 41% matriculation rate to those schools. Notable Trinity School alumni include Truman Capote, Ivanka Trump, and Oliver Stone.

  4. St. Paul’s School

    This private boarding school in New Hampshire is among the most selective college preparatory schools in the U.S. Serving just 533 students on its 2,000-acre campus, St. Paul’s attracts pupils from all over the world. Students study six days a week, with half days on Wednesdays and Saturdays to allow for athletics. St. Paul’s has several time-honored traditions and special holidays unique to the campus, including concerts with legendary bands like the Grateful Dead and Phish. The history of St. Paul’s is full of interesting stories, including the claim that the first hockey game in the U.S. was played on St. Paul’s ponds in 1883. Senator John Kerry, FBI Director Robert Mueller, John Jacob Astor IV, Michael Kennedy, and William Randolph Hearst are among St. Paul’s most notable alumni.

  5. Milton Academy

    Milton has long been recognized for its prestigious educational values, producing graduates that go on to do great things. Alumni include several members of Congress, Medal of Honor recipients, and Nobel Laureates. Historically, Milton has been a feeder school for Harvard University. Some of the incredible amenities found on Milton’s campus include the Ruth King Theater (a gift of novelist Stephen King) and the Ayer Observatory which is home to a dome refractor. Both Robert F. and Ted Kennedy were educated here, as well as Nobel Prize-winner T.S. Eliot, current Governor of Massachusetts Deval Patrick, and former U.S. Attorney General Elliot Richardson.

  6. West Nottingham Academy

    Founded by Samuel Finley, a former president of Princeton, West Nottingham Academy is the oldest boarding school in the United States. The academy has educated many prominent colonial Americans, including two signers of the Declaration of Independence: Benjamin Rush and Richard Stockton, as well as John Filson, the founder of Cincinnati, Ohio. The campus is on the U.S. National Register of Historic Places, and many of the buildings are considered to be historic pieces of architecture. West Nottingham’s small athletics community has risen to prominence, boasting a successful figure skating program with Olympic athletes.

  7. Deerfield Academy

    Founded in 1787, Deerfield is among the oldest prep schools in the U.S., and is rumored to attract some of the most prestigious students, including European royalty. Even early on, Deerfield produced influential alumni that became the governors and congressmen of New England. Deerfield graduates include Medal of Honor recipient Rufus Saxton, Thomas Keating, gold medalist Allen Stack, members of the Rockefeller family, and Matthew Fox. Many Deerfield students go on to study at top-tier schools. Impressively, the academy is home to its very own printing press, Deerfield Academy Press, which publishes the work of student and faculty members.

  8. Choate Rosemary Hall

    Deerfield’s fierce rival, Choate Rosemary Hall, stands up to its reputation with an incredible history of excellence, with many students regularly participating in high-level academic, scientific, and artistic competitions like the American Mathematics Competitions and performances at St. Peter’s Basilica in Rome. The campus is home to many historic sites, including the 1774 homestead with a secret passage that may have been a part of the Underground Railroad. Some of Choate’s most famous alumni include President John F. Kennedy, Edward Albee, Jamie Lee Curtis, Glenn Close, and Nicholas Negroponte.

  9. Horace Mann School

    Horace Mann is continually ranked as one of the best prep schools in the country, with a highly selective admissions process and a high rate of admissions to the most exclusive colleges including Harvard, Yale, and Princeton. The school was founded as an experimental unit of the Teachers College at Columbia University, so naturally, Horace Mann graduates often matriculate to Columbia as well. Located in the Bronx neighborhood of New York City, students are able to study in the school’s 100-acre nature laboratory in Connecticut for a week at a time. Horace Mann has graduated several notable alumni, including former U.S. Attorney General William Barr, Jack Kerouac, William Carlos Williams, and Pulitzer Prizewinners Robert Caro and Elliott Carter.

  10. Brearley School

    Considered the sister school of several prep schools including the Collegiate School, Spence, and Chapin School, Brearley is one of the most prominent all-girls private schools in the U.S. Top college destinations for Brearley graduates include Yale, Harvard, Columbia, Princeton, Williams College, and Johns Hopkins University. Brearley boasts many famous women as their graduates, including Caroline Kennedy, silver medalist Emily Cross, and Kyra Sedgwick.