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June 22, 2026

The Scholar-Athlete: Why Middle School Sports Are the Secret to Classroom Success

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.

June 17, 2026

The 5th Grade Pivot: Why Families Switch to Kent School for Middle School

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.

June 16, 2026

Kent School SGA 2025 School Year

A Premier Private School Alternative for Queen Anne’s County & Centreville

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.

June 16, 2026

Kent School students having fun and smiling for the camera

Public vs. Private School in Kent County: Finding the Right Path for Your Child

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.

June 13, 2026

Renovation begins in the middle school at Kent School

Kent School Begins Middle School Renovation as Part of the Together We Soar Campaign

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.

May 28, 2026

Kent School Middle School students gathered around smiling

Navigating Friendship Conflicts with Care 

Friendship conflict can be one of the most painful parts of growing up, especially during the middle school years. In this thoughtful piece, Kent School’s Dean of Students explores the difference between bullying and social conflict, why accountability matters, and how schools and families can work together to help children navigate difficult friendships with empathy, courage, and care.

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We believe an exceptional education should be within reach for every family. Our tuition assistance program is designed to make a high-quality independent school experience accessible to a diverse range of students.