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The Hill School was founded in 1851 by the Rev. Matthew Meigs as the Family Boarding School for Boys and Young Men. However, it has been known as the Hill School since at least 1874.
The school opened on May 1, 1851, enrolling 25 boys for the first year. According to Paul Chancellor's The History of The Hill School: 1851-1976, "He [Meigs] wanted to stress that he was not founding still another academy, but a type of school quite new and rare in America. There is a tendency to think that the boys' boarding school as we know it existed as long as there have been private schools. It has not.... The Hill was the first to be founded as a "family boarding school" (a school where the students lived on campus), as opposed to boarding with families in the town."
In 1998, the school became coeducational, enrolling 88 girls in its first year.
In the early 20th century, The Hill was a feeder school for Princeton University; a prominent "The Hill School Club" operated at Princeton for the benefit of alumni. The prevalence of Hill alumni, as well as those of Lawrenceville, Hotchkiss, Exeter and Phillips Academy at Princeton, led F. Scott Fitzgerald to lament that it was those of 'lesser' preparatory schools which were more prepared for the fray. The admissions process was relaxed for Hill School students, with cases including George Garrett, Princeton 1952, who was admitted when he confessed that he liked the striped football uniforms. At one point, Lawrenceville and Hill sent more students to Princeton than all public schools combined. Today, Hill alumni attend a wide variety of colleges.
The Hill School offers classes in each of its nine academic departments and offers 28 Advanced Placement courses.
The Hill School offers classes in Chinese, French, Spanish, Arabic, Latin, and Ancient Greek.
In the early days of the school, boys played shinney, town ball, football and cricket. Matthew Meigs was not an athlete yet allowed sporting pursuits, unlike his contemporaries such as Samuel Taylor of Phillips Academy. During John Meigs' tenure as headmaster, organized and interscholastic sports began at The Hill. Tennis became the dominant sport during this period, unlike baseball at other schools.
The Hill School is a member of the Mid-Atlantic Prep League (MAPL), which the School joined in 1998. The Hill School was a charter member of the Pennsylvania Independent Schools Athletic Association (PAISAA), which became an officially sanctioned organization in 2011. In 2014, The Hill School received associate membership in the New England Preparatory School Athletic Council (NEPSAC).
The Hill School's rivalry with Lawrenceville dates back to 1887. It is the fifth-oldest high school rivalry in the United States. Originally an annual football game, the schools compete against each other in all of the fall sports on either the first or second weekend in November.
Peddie School also maintains a "Hill Day" during which several teams from Hill and Peddie compete.
Participation in athletics is considered a vital part of a Hill education. All third and fourth form students must participate in at least two seasons of interscholastic sports, and all fifth and sixth formers must play at least one interscholastic season. Students may fulfill a season requirement by serving as a student athletic trainer or team manager.
The Hill School has been described as different in style and spirit from its counterparts in New England, and has been described as strict and demanding. It has also been described as conservative.
Alumnus Oliver Stone described his experience at The Hill School: "I hated the Hill School at the time. It was monastic. Horrible food, no girls. It was truly one of those Charles Dickens' types of experiences. And I really hated it. Years later I came to appreciate it. I think the inquiry and above all the discipline, of studying and concentrating and sitting down and doing it." The Hill has been criticized, alongside other East Coast Protestant schools, for promoting "snobbish", undemocratic, and "un-American values".
E. Digby Baltzell's book The Protestant Establishment identified the Hill School as one of the "select sixteen" best boarding schools in the United States. In the late 19th and early 20th centuries, two of the 21 richest Nouveau riche families sent their sons to The Hill.
^"The Hill School, Pottstown, USA", Charterhouse School. Accessed March 13, 2017. "The relationship between Charterhouse and The Hill School, Pottstown, USA, started in 1994 and has developed into a strong working partnership that has seen regular science trips (every year for over 10 years), a theatre trip, choir visits, football matches, and a teaching exchange."
^Levine, Steven B. (1980). "The Rise of American Boarding Schools and the Development of a National Upper Class". Social Problems. 28 (1): 63-94. doi:10.2307/800381. JSTOR800381.
^Fleener, Sarah. "Cameras roll on The Hill for film about unlikely champs", The Mercury (Pennsylvania), June 19, 2007. Accessed March 13, 2017. "The feature film Our Lady of Victory came on location to the Hill School's campus to film several scenes in the Gillison Gymnasium, hallways, and locker rooms. The independent film, described by the film's writer and director Tim Chambers as 'a true Cinderella story,' captures the 1972 Immaculata College girls basketball team's unlikely rise to the national championships."
^Seated Meals in the Dining Room, The Hill School. Accessed January 7, 2018. "Constructed in 1914, the present Dining Room was the first distinguished accomplishment of The Hill's third headmaster, Dwight Meigs, grandson of our founder, the Reverend Matthew Meigs."
^Staff. "Hill School Gets New Headmaster.", The New York Times, May 21, 1922. Accessed January 5, 2018. "Elaborate ceremonies this afternoon marked the induction into his new position of the Rev. Dr. Boyd Edwards, formerly of Orange, N.J., as headmaster of the Hill School."
^Brandt, Evan. "Maine educator chosen to lead The Hill School", The Mercury (Pennsylvania), November 14, 2011. Accessed January 6, 2018. "An assistant headmaster at a Maine private school has been selected as the new Hill School headmaster it was announced Monday. Zachary Gimbel Lehman, 38, who has served for six years as the assistant head of school for advancement at Gould Academy in Bethel, Maine, will take over for retiring Headmaster David R. Dougherty, who, with his wife Kay, will retire on June 30, 2012 after 19 years of service to the school."