Skip To Main Content
TheWhitfieldSchool-white logo

Experiential education for grades 6-12 in St. Louis

Head of School

The Whitfield School experience is centered on growth—fostering strength of character, academic excellence, and engaged citizenship. Our commitment is to provide your child with the skills, resilience, and confidence to thrive in an ever-changing world.

Chris Cunningham

Chris Cunningham, Ph.D.
Head of School

Dear Friends,

At The Whitfield School, we believe that academic rigor and joy in learning are not opposing forces—they are partners. True rigor invites curiosity, demands persistence, and grows best in an environment where students feel known, challenged, and supported.

Our teachers design experiences that ask students not just to learn about the world but to engage with it. Whether debating ethical dilemmas in philosophy, prototyping designs in engineering, or analyzing literature through performance, students are active participants in their learning. They make choices, take risks, and reflect deeply on their process—discovering that understanding comes not from memorizing answers, but from wrestling with questions.

This is what we mean by experiential, inquiry-driven education. Learning by doing builds confidence, adaptability, and a sense of purpose. It develops thinkers who are as comfortable with uncertainty as they are with achievement—students who know how to collaborate, communicate, and create meaning from complexity.

Whitfield’s culture of care ensures that challenge never stands alone. Our educators coach and encourage, cultivating a balance of high expectations and unwavering support. In that balance, students grow not only in intellect, but in empathy, self-awareness, and resilience.

Every day, I am reminded that Whitfield’s strength lies in its people—in the relationships between teachers and students, and in a community that values character as much as accomplishment. Here, young people learn how to lead with integrity and imagination, prepared not only for college, but for a lifetime of purposeful engagement with the world.

I invite you to visit our campus and experience the momentum for yourself. You’ll find a school where learning is alive, where rigor is human, and where students are empowered to grow into their best and truest selves.

Warmly,



Chris Cunningham, Ph.D.
Head of School

About Dr. Cunningham

Chris Cunningham became Head of School in 2022. A lifelong educator and published author, Dr. Cunningham came to Whitfield with more than 25 years of experience in independent schools. In and out of the classroom, he has always valued the relationships he builds with students, finding joy in helping them explore ideas, discover intellectual passions, and grow as human beings.

Before coming to Whitfield, Dr. Cunningham spent nearly two decades at The Lawrenceville School in New Jersey, where he served in a range of capacities, including English teacher, coach, dorm head, Dean of Faculty, and ultimately Assistant Head of School. His leadership at Lawrenceville included initiatives in faculty development and innovative teaching—particularly advancing the school’s hallmark Harkness method of discussion-based learning. Dr. Cunningham’s long experience with student-centered teaching made for a natural transition to Whitfield’s own emphasis on experiential, collaborative classrooms. Prior to Lawrenceville, he taught English at Princeton Day School, Stuart Country Day School, and Montclair Kimberley Academy. 

A Phi Beta Kappa graduate of Stanford University with a degree in Modern Thought and Literature, Dr. Cunningham earned his Ph.D. in modern American literature from Duke University. His wife, Helena, is herself a lifelong educator who taught French for more than three decades at Lawrenceville. She now serves as the costume designer for Whitfield’s theater productions. The Cunninghams have two adult children. Outside of school, Dr. Cunningham is a dedicated runner and reader, and his poetry, book reviews, and literary criticism have appeared nationally in numerous literary journals.

A Note from Chris