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.