Athletics are about more than competition. At Kent School, middle school sports help students develop resilience, confidence, teamwork, and focus, skills that support success both in the classroom and beyond.
As children approach middle school, many families begin asking whether their current school still feels like the right fit. At Kent School, Middle School begins in Grade 5, giving students the chance to build confidence, leadership, independence, and critical thinking skills in a small-by-design K-8 community.
Searching for a private school near Centreville, MD? Discover Kent School’s unique program in Chestertown with small classes, academic rigor, Chesapeake Bay studies, and more.
Comparing public and private schools in Kent County, Maryland? This guide helps families understand how class size, middle school structure, hands-on learning, tuition assistance, and school community can shape the right school choice for their child.
The Deborah C. Williams Middle School renovation is designed to modernize and enhance educational spaces, providing students and faculty with updated classrooms that support collaboration, creativity, and innovative teaching practices. The project is part of the broader Together We Soar campaign, which also includes the construction of the new Osprey Innovation Center and continued investment in Kent School’s endowment.
Families searching for a private school in Chestertown, Maryland are often looking for more than academics alone. At Kent School, students are known, challenged, encouraged, and given room to experience the joy of childhood while building confidence, curiosity, and critical thinking skills.
At Kent School, our nine-year partnership with the Center for Transformative Teaching and Learning (CTTL) at St. Andrew’s Episcopal School ensures that our classrooms are shaped not only by experience and passion, but by research. We are proud to be the only PK–8 school in Maryland engaged in this nationally recognized, research-informed professional training.
Choosing an independent school is a significant financial decision for any family. At Kent School, we view tuition not as a fee, but as an investment in a child’s foundation. Here is the Truth about the value that investment returns to our students. At Kent School, we...
At Kent School, middle school is more than just a bridge to high school—it’s a time of real growth. With small class sizes, hands-on Chesapeake Bay learning, and a community that supports every child, Kent School offers a unique experience among private middle schools on Maryland’s Eastern Shore.
If you’re a parent exploring private school options for your child, chances are you’ve asked yourself: “Can we actually afford this?” It’s a common and completely valid question. For many families, “affordable” doesn’t mean cheap — it means attainable, flexible, and worth the investment.