Lifestyle August 26, 2025

Back to School on the Eastern Shore:

What Families Need to Know

Back-to-School Season on Maryland’s Eastern Shore

As summer winds down, the Eastern Shore comes alive with fresh routines, school buses on the move, and the excitement of a new school year. Families living in Kent County, Cecil County, Queen Anne’s County, Talbot County, and Kent County, Delaware know that strong schools and welcoming communities are at the heart of what makes this region such a special place to call home.

If you’re considering a move, back-to-school season is the perfect reminder that the right home goes hand in hand with the right neighborhood and school district.

Strong Schools, Strong Communities

The Eastern Shore offers excellent educational opportunities for families. Schools in Chestertown, Easton, Centreville, Chesapeake City, and Rock Hall provide strong academic programs, competitive sports, and a wide range of extracurriculars.

For homeowners, being in a desirable school district can also boost property values and make your home more attractive to future buyers. That’s why our Coldwell Banker Chesapeake agents guide families in finding not just the right house, but the right school community.

👉 Visit our Community Pages to explore schools and neighborhoods across the Shore.

Tips for Moving During the School Year

Relocating with kids in the middle of a school year can feel overwhelming, but it doesn’t have to be. Here are some ways to make the transition smoother:

  • Research School Districts in Advance – Review bus routes, after-school programs, and extracurricular activities.

  • Choose a Family-Friendly Floor Plan – Homes with mudrooms, extra storage, and homework areas help busy families stay organized.

  • Get Involved Early – Join parent associations, youth sports leagues, or local clubs to build connections quickly.

Coldwell Banker Chesapeake agents know how to help families settle into the right neighborhood, making the move seamless for both parents and children.

Back-to-School Home Organization Tips

The start of school is the perfect time to get your home organized. Families on the Eastern Shore love features such as:

  • Dedicated Homework Stations – Quiet, well-lit areas to help kids focus.

  • Organized Entryways – Hooks, cubbies, and storage to manage backpacks, sports gear, and shoes.

  • Flexible Spaces – Rooms that evolve with your family’s needs, from playrooms to study spaces.

Looking for a home that fits your family’s lifestyle? Start by browsing our current listings.

Community Life Beyond the Classroom

Back-to-school isn’t just about school supplies — it’s also about reconnecting with community life. Across the Shore, families enjoy events like:

  • Queen Anne’s County Fair

  • Chestertown First Fridays

  • Easton Waterfowl Festival

  • Rock Hall’s Fall Fest 
  • Downrigging Weekend in Chestertown
  • Local football games and fall festivals

These events bring neighbors together and highlight why life on the Eastern Shore is so special.

Find Your Perfect Home This School Year

At Coldwell Banker Chesapeake, we know that back-to-school season is about more than just academics — it’s about creating the right foundation for family life. Whether you’re relocating for work, moving for schools, or looking for more space, our team is here to help you every step of the way.

Coldwell Banker Chesapeake Real Estate Co.

🌐 www.cbchesapeake.com

📍 Easton: 17B N. Harrison Street, Easton, MD 21601 — 410-822-9000
📍 Chestertown: 114 B S. Cross Street, Chestertown, MD 21620 — 410-778-0330
📍 Chesapeake City: 200 Bohemia Avenue, Suite 2, Chesapeake City, MD 21915 — 410-885-2200

🏆 #1 Coldwell Banker in Maryland 2023 & 2024