Meet Our Head of School

Holton-Arms School’s eighth Head of School Penny B. Evins has an exceptional record of building strong, lasting relationships and motivating those around her to be the best versions of themselves. Mrs. Evins brings 25 years of independent school experience to her headship at Holton. Most recently, she served as Head of School for Collegiate School in Richmond, Virginia, and St. Paul’s School for Girls in Baltimore, Maryland. 

Mrs. Evins comes to Holton from Collegiate School where she led the School’s nearly 2,000 community members through its successful COVID reopening efforts, propelled record enrollment, and enhanced family, donor, and Board engagement. During her six-year tenure at St. Paul's School for Girls in Baltimore, which included an early childhood center and coordinate program with St Paul’s School, she successfully led the school's healthy growth in enrollment and curriculum development. The advent of experiential real-world opportunities for students through its SPIRITUS Scholars Program, a multi-year exploratory program, encouraged the application for and award of a prestigious E.E. Ford Foundation Grant for the school. Upon her departure as a beloved leader, the Board of Trustees at the St. Paul’s Schools established “The Penny B. Evins Fund,” which supports innovative endeavors, and the creation of a modern learning commons, named in her honor as “Penny B. Evins Learning Commons.”

Prior to her service in headships, she held a range of leadership positions, including division head of middle and lower schools, lower, middle, and upper school counselor posts, and admissions and strategic planning consultation. Currently serving as a Trustee to the National Association of Independent Schools (NAIS) as a member of the Executive Committee and The Heads Network, she formerly was a Trustee of the Association of Maryland and DC Schools (AIMS), the Center for Spiritual and Ethical Education (CSEE).

Penny is a professional mentor for aspiring heads and independent school leaders and a frequent presenter on emerging trends in independent schools.
A native of New Orleans, she attended Isidore Newman School and is a graduate of Choate Rosemary Hall in Connecticut. She received a Bachelor of Arts in English and a Master of Education in counselor education from the University of Virginia.

As she makes Holton her home, she will be joined by her husband Sam V, whom she met while they were both working at his alma mater, the Lovett School in Atlanta, her college-aged children Sam VI and June Friend, along with their cat Gumbo and dog GiGi. A lover of outdoor activities, she and Sam look forward to exploring the many opportunities in our neighboring trails and park systems. She is excited to immerse herself in the School’s welcoming community of students, families, alumnae, and graduates, and supportive friends. Most of all, she looks forward to honoring Mrs. Holton’s clarion call “that they who enter through the Open Door of Holton-Arms remember that they felt, in the friendliness of a home, the urge to learn and the joy of overcoming obstacles as the way to happiness and the fullest life.”