1956 - There were 126 students enrolled at The Chestnut Hill School from preschool through Grade Four. Under the headship of Miss Wendy Lamont, funds were raised to purchase four acres of land adjacent to the school. 

1968-69 - The Lee Building was constructed; the school added a new athletic field, and added a Fifth and Sixth Grade. The Lee Building was free standing and was the precursor to the current gym. 

1970’s - Mr. Foster Joseph Allison became Head of School, and began to draw students from a wider geographic area. 

1982 - Mrs. Karan Merry, a former teacher at The Chestnut Hill School, became Head of School.  Mrs. Merry brought to her position an unprecedented focus on multiculturalism. The School became one of the first in the country to have a Multicultural Assessment Plan performed by NAIS. 

1984 - Mrs. Merry oversaw the construction of new classrooms for Kindergarten, 4th, 5th and 6th grades, linking the original school and the Lee Building. In 1987, swimming and wading pools for camp were added. 

1992 - The first Festival of Lights presentation was held to acquaint students with holiday traditions around the world. Mrs. Merry brought national attention to the School through her election as NAIS Board President in 1992, the first person of color to hold that position and as a Director for AISNE. At the end of Mrs. Merry’s long tenure with the school, a new gymnasium, large enough to host interscholastic sporting events, with additional classroom space beneath it were added to the school’s footprint.  

1996 - Mrs. Susan Bryant became Head of School. Enrollment at the school was 175 students with one class per grade level. Mrs. Bryant’s leadership emphasized community and she added “Open Circle,” a social competency program, to the curriculum. She continued the School’s commitment to diversity and multiculturalism.

2000 - Dr. Gregory Blackburn was named the next Head of School. Under Dr. Blackburn’s leadership, the school completed a large-scale building expansion project  in 2003. This project included an Early Childhood wing, built to meet the needs of the school’s youngest students. The project also improved communal spaces, adding a Community Meeting Room (CMR) that would serve as a lunchroom and theater. The design of the new school building exemplified the sense of community central to the school’s mission.

2003 - Dr. Blackburn continued to advance the school’s commitment to diversity, and CHS received the NAIS Leading Edge Program Award for Equity and Justice.

2007 - Dr. Steven Tobolsky became the next Head of School. A Campus Master Plan was undertaken that year, resulting in an expanded athletic field, an outdoor amphitheater, and updated playground spaces. Under Dr. Tobolsky, a focus on Upper School leadership resulted in the implementation of the Grade 6 Advisor Program and an enhanced athletics program. The school dedicated increased resources for Learning Specialist support and broadened the school’s capacity to meet the needs of its students through increased utilization of a Student Support Team, a full-time nursing and wellness position and expanded affinity group offerings. 

2017 - Ms. Tamara Schurdak joined The Chestnut Hill School as the next Head of School. CHS documented a healthy increase in student enrollment and benefited from reinvigorated annual fund giving under Ms. Schurdak’s guidance. The school also made a number of improvements under Ms. Schurdak including enhanced security features, major upgrades and additions to the school’s playgrounds and new carpeting throughout the building. 

2022 - Ms. Diana Blazar, formerly the Dean of Faculty/Academic Dean, took the reins as Interim Head of School.

2023 - Dr. Roderick MacNeal, Jr., is welcomed as the next Head of School.