2016-Present: Charles M. Stillwell
"He is a proven leader of deep moral character and inspiring intellect, with a passion for educational excellence. Sharing both the values and ambitions that our community holds dear, Charley is ideally suited to build upon the great legacy of The High School." – Bailey Patrick '79, then-Chairman of the Board of Trustees
Charley understands boarding schools, having spent much of his life around them: born and raised on a boarding school campus; attending one as a student; and later teaching at them. He is familiar with the unique and empowering relationships that are fostered between and among students and their teachers. His experiences over the last three decades in both boarding and day schools, including 18 years of experience as a head of school, prepared him to take the helm of Episcopal High School.
Charley received his bachelor’s degree in American history with honors from Princeton University, where he was a four-year member of the lacrosse team. Upon graduation, he joined the faculty of St. George’s School in Newport, R.I., where he taught history, coached JV girls’ basketball, varsity football, and boys’ lacrosse. He also served as a dorm parent, all while earning his master’s degree in American history from Brown University. He later taught at the Collegiate School in Richmond, Va., and the Gilman School in Baltimore, Md., where
for four years he served as Head of the Upper School before becoming the Headmaster at St. Christopher’s School in Richmond beginning in 1998. Charley has traveled extensively and served as the Vice President for North America of the International Boys’ Schools Coalition Board.
He has served as the President of the Virginia Association of Independent Schools, on the board of the Mid-Atlantic Episcopal School Association, and is currently a member of the Executive Committee of The Headmasters Association.
During his 18 years at St. Christopher’s, Charley led the efforts to expand community and global outreach, developed initiatives for student, academic, and arts programming, and spearheaded the development of a new athletics facility, leadership center, and dining facility. In addition, he significantly increased the school’s diversity and strengthened its financial standing.
Charley and his wife Sallie live on campus with their dog Ralph. They have two sons, John and Henry, and a daughter, Janie ’18.