About
Welcome! From our family to yours.
We hear it every day from parents, teachers, students, and even first-time visitors: Oakwood feels like family. It’s a safe, encouraging, loving home where children thrive. And no wonder—creating that kind of educational experience is a family tradition. In 1959, my grandmother, Gwen Riches, started our sister school, Pinewood, in the family home in Los Altos—where Pinewood School still flourishes today.
As a parent, I know you have many questions as you seek the best education for your child. So please explore the web site, call, or email. But above all, I invite you to visit us. At Oakwood, everything we do reflects the educational philosophy that our founder set forth more than fifty years ago: a more intentional education that shapes the growth of confident, vivid, thoughtful, high-achieving young people, fully prepared for the top colleges in the nation and life beyond.
Come meet our vibrant students, who can’t wait to tell you how much they love school. Chat with our expert teachers, who inspire, challenge, and encourage each student every day. Sit in on a dynamic class discussion, watch a performance of our latest musical, or tour the wide-open, sunlit grounds where our students gather, play, compete, and create.
If Oakwood feels as much like home to you as it does to us, we hope your family will become part of ours.
We look forward to meeting you.
Michelle Helvey
Head of School
Oakwood feels like family. That’s because we are a family. We’ve been one from the beginning.
Our History
Our story began in 1959, when Gwen Riches, an educator and artist, gathered her children and their friends for an afterschool arts program in her Los Altos home. As the children happily played, practiced, created, and performed, word began to spread. Mrs. Riches and her husband welcomed more and more children, eventually expanding the circle to hundreds of students. The Riches’ family home became Pinewood School, which still thrives today in Los Altos.
Founded and managed by Gwen Riches’ eldest granddaughter and her husband, Oakwood School in Morgan Hill began as a preschool through eighth grade school. In 2005, the high school grades began and in 2009, Oakwood graduated its first senior class. Today, the preschool through twelfth grade school flourishes on a 30-acre campus. As Pinewood’s younger sister, Oakwood carries on the educational tradition set forth by our “founding mother”—shaping our students’ growth with intention, intelligence, and unbounded joy.
When people visit the campus, they feel there is something quite special at Oakwood. The reason for this is no secret. When children are taught in a small and nurturing classroom environment by subject-focused teachers who love what they do, wonderful things happen. Add to that a strong curriculum, broad extra-curricular opportunities and beautiful facilities and you have an educational opportunity that is unmatched in the area.