Eight Schools Association

It was formally established in 2006, but has existed in some form since the 1973–74 school year. Although several ESA schools no longer publish their endowment figures, in 2016 the ESA contained seven of the ten wealthiest traditional college-preparatory boarding schools in the United States, as measured by total size of endowment. All eight ESA members commit to provide financial aid equivalent to the full demonstrated need of the U.S. citizen students that they admit, as determined by the schools' respective financial aid departments.

1973–2006: Informal association

During the 1973–74 school year, the heads of Andover, Choate, Deerfield, Exeter, Hotchkiss, Lawrenceville, and St. Paul's agreed to meet on a yearly, albeit informal, basis. After the first meeting, Northfield Mount Hermon was invited to join. According to Choate's website, the purpose of the ESA was "to show a connection between these [member] schools in academic philosophy, admissions standards, and athletic pursuits."

In 1996, the ESA agreed to add a second annual meeting to its calendar, with one meeting for the heads of school and the other for representatives of each school's boards of trustees.

The ESA will not expand unless the eight member schools unanimously agree, and no new members have been added since 1974.

2006–present: Formalized group

In April 2006, the ESA schools established a more formal administrative structure, appointing a president, vice president, and executive director. These roles were staffed by administrators of the member schools (i.e., not full-time ESA employees), who would rotate every three years. The ESA also adopted bylaws which state that the ESA's primary purpose is to "address critical educational issues in order to ensure the best educational experiences and outcomes for students, explore new research and trends in education, and develop collaborative programs."

The ESA heads have continued their annual meetings since formalizing the ESA. Topics discussed at ESA meetings include economic difficulties in the private school industry, ways to improve boarding school affordability, and the economic feasibility of need-blind admissions. Previous invitees and speakers at these meetings include Harvard Graduate School of Education professor James P. Honan, former Dartmouth College president James Wright, journalist Steven Brill, and education policy specialists.

Although several ESA schools no longer publish their endowment figures, in 2016 the ESA contained seven of the ten wealthiest traditional college-preparatory boarding schools in the United States, as measured by total size of endowment. (In 2017, the endowments of Kamehameha Schools in Hawaii ($11.0 billion) and the Milton Hershey School in Pennsylvania ($13.7 billion) were each larger than that of all the ESA schools combined. However, those two schools focus on educating specific subsets of the American population: Native Hawaiians and low-income students. Reflecting their different financial models, they also charge much lower tuition than the ESA schools—in Milton Hershey's case, none.)

Reflecting these financial resources, as of the 2023–24 school year, all eight ESA members commit to provide financial aid equivalent to the full demonstrated need of the U.S. citizen students that they admit.

Athletics

Although the ESA schools are geographically dispersed, making it somewhat impractical to schedule consistent sports matchups, several ESA schools have sought to schedule each other in out-of-conference play. The ESA held wrestling and basketball tournaments in 2007 and 2009.

The closest step to formal athletic cooperation came in 2015 when five ESA members—Andover, Choate, Deerfield, Exeter, and NMH—agreed to form an athletics association. A sixth ESA member, St. Paul's, eventually joined the group. The Six Schools League, as it is now known, is not a registered athletics league under the New England Preparatory School Athletic Council. In recent years several SSL teams have begun to characterize their relationship as "compet[ition] within the Eight Schools Association," as opposed to membership in the SSL proper.

Student and faculty cooperation

After formalizing the ESA, the schools identified several possible ideas for future cooperation, such as "a debate invitational, a joint literary publication, athletic play days, [] a musical group jamboree," and "collaborating on critical issues like pandemic preparedness."

In the years immediately following the establishment of the ESA, the group conducted several joint projects:

• Faculty conferences. The schools have occasionally scheduled faculty conferences, such as the 2007 arts conference, the 2010 science conference, the 2010 language/cultural conference, and the 2012 and 2013 education technology conferences.
• Student publications. In August 2007, Deerfield published 8 × 8: Writings from the Eight School Association, a collection of student writing curated by teachers and student editors at the ESA schools. In the preface, Deerfield's head wrote that she hoped future editions of the collection would "fost[er] intellectual relationships among its members." In 2019, Andover's student newspaper attempted to survey the student bodies of all eight ESA schools, but for various reasons, four of the eight schools did not participate.
• Arts festivals. ESA schools have also hosted a jazz festival (April 2008) and drama festivals (April 2010).
• Student competitions. As of 2010, ESA administrators were planning a "green campus" competition to encourage students to participate in environmental initiatives.

• Ten Schools Admissions Organization