Charley Stillwell understands boarding schools. He has seen how they operate from the inside as the child of a boarding school faculty member, as a student, and as a boarding school faculty member himself. 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 for 9th grade girls and 9th and 10th grade boys, all while earning his master's degree in American History from Brown University. After six years at St. George's, Charley went on to teach and coach at Collegiate School in Richmond, Va., and later moved to the Gilman School in Baltimore, Md., where for five years he served as head of the upper school. Charley served as the headmaster of St. Christopher’s School in Richmond beginning in 1998 until his arrival on the Hill in the summer of 2016.
A passionate educator, Charley is determined in his pursuit of excellence in academic and student life programming, global outreach, strategic growth, and student-faculty relationships. He has traveled extensively and served as the vice president for North America of the International Boys Schools Coalition
Board. In his educational philosophy, he wrote:
"Students thrive when they are part of a learning community based on close and supportive relationships with the faculty, high ethical standards, rigorous expectations for achievement, and a rich variety of learning opportunities through which they can discover their interests and passions. A great school develops the whole child. It ensures that each student develops the impressive academic skills, strength of character, and other personal qualities necessary for future academic success and for effective, positive leadership in this quickly changing world."
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.
A native Virginian, Charley is a graduate of Woodberry Forest School, where his father, John, was a beloved and longtime faculty member and administrator. He has served as the president of the Virginia Association of Independent Schools
and on the board of the Mid-Atlantic Episcopal School Association
, and he is the vice president and member of the Executive Committee of The Headmasters Association
Charley and his wife, Sallie, live on campus. They have three children: John, Henry, and Janie '18.