Head of School Message

Our thoughtful academic progression, featuring rigorous academics in an intentionally small setting, develops confidence, connection, and a lasting love of learning.  From our highly regarded Montessori Early Childhood Program through the International Baccalaureate Middle Years Programme, we bring together exceptional teaching, an integrated approach to executive function skills, and a closeness of community that larger institutions cannot replicate.  

Generations of graduates—now leaders, innovators, and engaged citizens—carry the Red Oaks experience with them.

Our Lower School, serving Early Childhood through Grade 4, occupies a building that was once a home—and still feels like one. Beyond the iconic porch and sheltering trees, the historic Cutler Mansion offers a world at once familiar and whimsical.  Mixed-age classes mean that every student receives just what they need – an education that is more responsive and personalized than traditional single-aged classes can offer. Our Montessori approach, complemented by focused instruction in math and writing, builds strong academic foundations alongside independence, agency, and curiosity.

Our fully renovated Middle School, serving Grades 5 through 8, sits a short distance up the road, with bright, modern spaces designed for teens and preteens. Here, students find a warm, vibrant community where they can explore their interests, take on new challenges, and develop the confidence and skills to set them apart.  Our world-renowned International Baccalaureate (IB) curriculum prepares students academically, socially, and emotionally for success wherever life takes them.  The results speak for themselves.  Our middle school graduates are sought after by and thrive in prestigious high schools and beyond.

At Red Oaks, we are unapologetically focused on what matters most: knowing children well, challenging them thoughtfully, and helping them grow into their best selves. Our values—Curiosity, Integrity, and Connection—guide how we teach, how we treat one another, and what we hope our students will carry into the world.

As you explore our website, I invite you to learn more about our programs and the opportunities we offer. Most of all, I encourage you to visit. Spend time in our classrooms, meet our teachers, and talk with our students. You will begin to understand how this small school creates such a lasting impact.  

With joy and gratitude,

Christopher Weaver 
Head of School

PS: And we’re not done yet. Read our new Strategic Plan, already underway, as we chart an exciting next chapter.