Moving to Maryland’s Eastern Shore: The Ultimate Family Relocation Guide

Moving boxes with packing tape

Considering a Move? Start With the Right School

Choosing to relocate is a major decision, especially when you have children. For most families, the search for the perfect home doesn’t begin with real estate listings—it begins with school reviews. The question isn’t just “Where will we live?” but “Where will our children thrive?”

At Kent School in Chestertown, Maryland, families find that answer. As a premier private K-8 school on Maryland’s Eastern Shore, we offer a nurturing, academically rigorous environment set in one of the most beautiful and welcoming waterfront communities in the Mid-Atlantic.

"Kent School makes it possible for us to live here full time. Otherwise, we would not have left the Bucks County (PA) area." — Kent School Parent

How Are the Schools on the Eastern Shore?

When relocating, the quality of education is the #1 priority. Families moving to Maryland’s Eastern Shore are often surprised by the depth of educational opportunities available. Whether you are looking at Kent County or neighboring Queen Anne’s County, the region supports a lifestyle change without sacrificing academic success.

In today’s era of flexible work, families are increasingly choosing where they want to live. Kent School provides the "educational anchor" that allows parents to trade the city commute for a life on the water.

Why Families are Choosing Chestertown and the Eastern Shore

Nestled within easy reach of Philadelphia, Baltimore, Washington, D.C., and New York City, the Eastern Shore offers a peaceful, safe alternative to suburban sprawl.

  • A Slower Pace: Enjoy a community-focused lifestyle in historic Chestertown.
  • Natural Beauty: Minutes away from the Chester River and the Chesapeake Bay.
  • Accessibility: Rural living with "big city" culture and healthcare just a short drive away.

Why Kent School is the Top Private School Choice

Located on a scenic riverside campus in Chestertown, Kent School stands out for families seeking a high-caliber independent school.

The Benefits of a K-8 School Model

Research in the American Educational Research Journal shows that students in K-8 schools demonstrate higher academic achievement and stronger school connectedness compared to the traditional middle school model. At Kent School, our 8th-grade leaders are the "top of the school," allowing them to stay younger longer while building the self-assurance needed for high school.

Affordability: A Private Education Without the City Price Tag

One of the best-kept secrets of moving to the Eastern Shore is the value. Kent School is significantly more affordable than independent schools in DC, Baltimore, or Philadelphia. Families can save thousands in annual tuition without sacrificing quality, faculty expertise, or secondary school placement success.

  • Tuition Assistance: We are committed to making a Kent School education accessible.
  • Loyalty Discount: Savings available for families with three or more children enrolled.

Plan Your Visit to Chestertown

If you are exploring a move to Maryland, we invite you to see our campus in person. Discover why we are the preferred choice for families seeking a private school on the Eastern Shore.

Schedule a Private Tour

Contact Us: 410-778-4100

6788 Wilkins Lane, Chestertown, MD 21620

We welcome families relocating to Chestertown, Rock Hall, Galena, Centreville, Easton, Annapolis, and more.

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About Kent School

Kent School is an independent Preschool through Grade 8 school located in Chestertown, Maryland. Rooted in joy, hands-on learning, and a deep respect for childhood, Kent School helps students grow with confidence, curiosity, and critical thinking skills. Our waterfront campus on the Chester River gives children room to explore, learn, lead, and become known as individuals.

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Explore Academics

From Preschool through Grade 8, Kent School’s academic program is designed to help students think critically, communicate clearly, and develop a lifelong love of learning.

Considering Kent School?

Families often discover Kent School while researching the right learning environment for their child. Our classrooms prioritize thoughtful instruction, small class sizes, and meaningful student engagement.