Head of Oakland School, Carol Williams, sits with students.

Welcome from Head of School

A Letter from Carol Williams

We are delighted you have chosen to learn more about Oakland.

It is my privilege to serve as the fourth director in Oakland’s sixty-year history. My time at Oakland began in 1978, and my passion for our school and students has only grown through my roles as residential instructor, classroom teacher, and now head of school.

Through my years and varied experiences, it became clear to me why Oakland is so special. More than just our peaceful country setting, Oakland’s community is entirely united around the success of our students. Our founder, Margaret G. Shepherd, instilled a passion for learning and achievement that remains a guiding principle and palpable force. We call this unique pedagogy the Oakland Way and have been using this approach for more than 60 years to successfully teach and empower students who learn differently.

As you consider educational options for your child, we invite you to discover Oakland and learn more about our individualized academic approach, emphasis on character, and included equestrian and summer camp programs.

Together, we can help your child build the strong foundation needed for future educational and personal success.

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Carol Williams
Head of School, Oakland School