Mission and History

List of 9 items.

• Jeremiah Peck

  1660–1662
  Hopkins Grammar School
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  For much of Hopkins’ early history, the position of Head of School was held by young Puritan clerics hoping to get a start in their career. This was true in the case of Jeremiah Peck, the first teacher at Hopkins Grammar School. As a four-year-old child, Peck had migrated with his father to Boston the same year that Edward Hopkins and John Davenport did (1637). He attended Harvard for three years before becoming a schoolmaster first in Guilford, then at Hopkins when it opened in 1660. After two years of teaching at Hopkins, Peck returned to Guilford and became the pastor at the Guilford Congregational Church.

• Hawley Olmstead

  1839–1849
  Hopkins Grammar School
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  Over time, the position of Head of School at Hopkins came to be held more and more frequently by students from the Divinity School at Yale, students whose focus was more often on their own studies rather than that of their students at Hopkins. This began to threaten the ability of the school to survive until the arrival of Hawley Olmstead. In 1839, the trustees hired this Phi Beta Kappa graduate of Yale with twenty years of teaching experience in Wilton schools to begin teaching in the new Hopkins school building at Wall and High Streets. He reportedly was much stricter with the students, but balanced his Puritan sternness with intellect, empathy, and a long-term commitment that made the students appreciate him. Enrollment climbed steadily, but after ten years at Hopkins, his eyes began to fail and he chose to resign.

• James M. Whiton

  1854–1864
  Hopkins Grammar School
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  Hawley Olmstead was succeeded by his son, Edward, but Edward lacked the skills and drive of his father, and enrollment began to plummet again. By 1854, when the trustees hired James Whiton, another Phi Beta Kappa graduate of Yale, the school’s situation had become quite dire. Only six students remained, and one of them died during the autumn when he fell out of a tree. Whiton was determined, however, and introduced many foundational hallmarks of the school experience familiar to students today: report cards, final exams, study halls, a Junior School, English composition, and arts courses. Enrollment climbed to over one hundred students for the first time, and he used the milestone of the School’s bicentennial to create an alumni association. Whiton left to become a pastor of a church in Massachusetts, but he participated in Hopkins alumni events until his death in 1920.

• Katherine Glendinning

  1907–1916
  The Day School
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  Although a Midwesterner by birth, “Miss Kate” went to Vassar before beginning her teaching career in Chicago. Then for four years, she taught in Montana before returning east to open her own school in New Haven in 1907. Initially, it was open to boys and girls of all ages, from primary through high school. Glendinning decided to sell her school to one of her teachers, Elizabeth Lewis Day, shortly before marrying Col. Harry F. Wanvig in 1917. The catalog for Miss Glendinning’s school began by stating: “The aim, as in all good schools, is the development of mind and character. The school strives to interest the pupils in their work and to develop systematic habits of study.” This statement of purpose continued to be part of the catalog even after the school became known as The Day School.

• George B. Lovell

  1916–1953
  Hopkins Grammar School
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  George Lovell is responsible for much of Hopkins’ modern identity. His 37-year tenure is the longest of any Head, and he helped usher Hopkins into its new character as a “country day school” on its current campus on the western edge of New Haven. Having been on the faculty when the school was nearly absorbed by the New Haven public school system in 1911, Lovell took the reins offered him by the Trustees and reimagined the school as more than simply the college admission test tutoring school it had somewhat become. Working with Trustees Simeon Baldwin and Henry Farnam, Lovell led the charge to purchase the Mitchell property in Westville, hired the first full-time athletic director to oversee the sports program, and supported new activities such as an orchestra, glee club, yearbook and literary magazine. He also found Helen Barton to lead the Junior School quite successfully for 42 years, providing scholars well prepared for the rigors of a reinvigorated curriculum in Hopkins’ upper grades. In addition to Baldwin Hall, Hopkins House and Reigeluth Gym were also constructed. In 1960, Lovell Hall was named in his honor.

• Mary Brewster Thompson

  1939–1952
  Prospect Hill School
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  While several individuals had a hand in the establishment of Prospect Hill School in the early 1930s, the decision to hand the reins over to Mary Brewster Thompson began to set Prospect Hill as a marker of academic excellence for girls in New Haven. A math teacher with degrees from Wellesley and Teacher’s College (Columbia) and experience in various New York schools, Thompson came to Prospect Hill with high recommendations. She helped establish new activities such as a school newspaper and an active community service program. She also guided the school through World War II, establishing a partnership with a school in France after the war to help it recover from the war. The Mary Brewster Thompson Award, established in 1960, remains Hopkins School’s highest academic honor. In addition, Hopkins named its most recent building on campus, Thompson Hall, in her honor.

• F. Allen Sherk

  1953–1974
  Hopkins Grammar School
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  When George Lovell retired from Hopkins after his lengthy tenure, he left big shoes to fill. Allen Sherk stepped in and guided the school through some tumultuous growth and change. His experience at Milton Academy shaped his approach to education at Hopkins, with an emphasis on educating “the whole child” and a fully engaged faculty. He oversaw the celebration of the school’s tercentenary and used it to successfully raise funds for the construction of Lovell Hall as a dining hall and arts center. He saw to the addition of modern science classrooms to Baldwin Hall and to the addition of the Learning Center (now the Calarco Library). Active in the larger independent school community, Sherk was an early member of the Connecticut Foundation for Independent Schools and the New England Association of Colleges and Secondary Schools. Trustees and alumni/ae most closely associate him with the decision to merge Hopkins Grammar School with Day Prospect Hill School to create a modern, coeducational school in 1972, now known as Hopkins School.

• Barbara Masters Riley

  2001–2016
  Hopkins School
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  By any of several measures, Barbara Riley belongs in this list of Notable Heads of School. While she was hailed as “the first woman Head of Hopkins” upon her selection, this overlooks the notable women who headed the girls’ schools before they merged with Hopkins Grammar School in 1972. Riley’s notability lies more properly in any of numerous other categories. Under her leadership, the endowment grew from nearly $25 million to something remarkable ($100 million). Both student enrollment and the number and quality of faculty and staff members increased. Academic programs were added, including the innovative MSON (Malone Schools Online Network). New campus buildings and other facilities emerged, while the quality of older ones was improved. These are all tangible measures. As notable, she improved the quality of life of the school community by exhibiting a deep caring for students, faculty, staff, and their families.

• Kai Bynum

  2016–2022
  Hopkins School
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  Kai Bynum cemented his place as a Notable Head of School during his tenure at the helm from 2016 until 2022. The first Head of color in the School's history, Bynum led Hopkins with passion, poise, and an unwavering commitment to students. His accomplishments include growing the school’s financial aid budget by over 50% in six years, strengthening Hopkins’ commitment to equity and inclusion, and innovating the academic program with interdisciplinary course offerings.  Perhaps the most notable aspect of Bynum's time at Hopkins was his management of the COVID-19 pandemic, which included the closure of campus in 2020 and operating in a hybrid model in 2020-21. Throughout unprecedented challenges, Bynum's steadfast leadership and attention to detail helped keep our community safe, connected and thriving.