According to John Chancellor’s The History of The Hill, “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. Most of the 12 to 15 schools generally considered the “core” group were established in the last half of the nineteenth century…Of this whole group of schools, The Hill was the first to be founded as a family boarding school."
Rev. Meigs' son, John Meigs, became headmaster in 1876 at the age of 24. In the 35 years that followed, the School grew from an institution with two teachers and 20 boys to a school of 40 masters and 375 young men. From 1911 to 1914, Alfred G. Rolfe served as headmaster, succeeded by Dwight R. Meigs, from 1914 to 1922. In 1920, ownership of the School was transferred from the Meigs family to Hill alumni, marking the beginning of a new era of alumni loyalty and service. Headmaster Boyd Edwards led the School from 1922 to 1928. Edwards was followed by James I. Wendell, credited with greatly expanding the physical plant and library resources. At the time of The Hill's centennial celebration, which attracted nationwide attention, Dr. Wendell announced his retirement, closing 24 years of leadership. Edward T. Hall was appointed to fill the void. In his 16-year tenure, Hall raised academic admission qualifications, enhanced scholarships and faculty salaries, and expanded the School's physical facilities. Upon his retirement in 1968, the Trustees appointed Archibald R. Montgomery III, who served until 1973, succeeded by Charles C. Watson.
David R. Dougherty served The Hill School from 1993 until June 2012. For 19 years he led the School through an era of transformation and growth, including the introduction of coeducation in 1998. Another initiative at Hill under David Dougherty was the creation of an Honor Code and Honor Council. The Hill's Honor Code, written to promote an environment of mutual, school-wide trust and respect, reflects the School's Motto, "Whatsoever things are true," a phrase at the heart of The Hill's educational philosophy since its founding in 1851.
The Hill’s first capital campaign (1998-2003) raised more than $85 million, sustaining and advancing excellence in every aspect of the School. Notable was the construction of new academic, residential, and athletics facilities: the Academic Center (1998); Dell Village Dormitories (1999); and the David H. Mercer Field House and Jerry Day ’37 Squash Center (2001).