To Maryland’s Eastern Shore

Thinking about making the move to Maryland’s Eastern Shore? You’re not alone. Every year, more buyers—retirees, remote workers, young families, and those looking for a slower pace—discover the unmatched charm of life along the Chesapeake Bay. With its historic towns, waterfront beauty, vibrant arts communities, and strong sense of local pride, the Eastern Shore offers something for everyone. But like any major life transition, moving here comes with a few things worth knowing up front.

Here are the Top 10 Things to Know Before Moving to the Eastern Shore, curated by local experts at Coldwell Banker Chesapeake, who know the region better than anyone.

1. The Lifestyle Is Slower—and That’s the Point

If you’re moving from a metro area like D.C., Baltimore, or Philadelphia, the pace of life on the Eastern Shore may feel like a welcome shift. Locals value conversation, connection, tradition, and community. Shops close earlier. People linger over breakfast. Traffic is minimal, and outdoor time is a priority.

This slower pace isn’t a drawback—it’s one of the region’s greatest assets. Many residents say their stress melts away within a few weeks of settling in.

2. Waterfront Living Is a Way of Life

The Eastern Shore is one of the East Coast’s premier waterfront destinations. With the Chesapeake Bay, Choptank River, Miles River, Wye River, and countless creeks and coves, waterfront living is woven into daily life.

Whether you’re looking for:

a private deep-water dock
panoramic Bay sunsets
a serene creekside home
or a property with boating access

…you’ll find an incredibly diverse range of waterfront properties.

But it’s important to understand flood zones, insurance requirements, and shoreline protections. A local agent with waterfront expertise—like those at Coldwell Banker Chesapeake—can clarify these nuances.

3. Small Towns With Big Personality

The Eastern Shore is known for its picturesque towns, each with its own charm:

Easton – arts, dining, and cultural hub
St. Michaels – premier waterfront community with tourism, boating, and boutique living
Chestertown – rich history, riverfront beauty, home to Washington College
Oxford – quiet, scenic, and perfect for a peaceful waterfront life
Cambridge – growing arts district and revitalized waterfront scene

What surprises many newcomers is how lively the cultural calendars are—live music, theater, festivals, farmers markets, historic events, and more.

4. You’ll Want to Learn the Bridges and Back Roads

Most residents learn quickly that the Bay Bridge and local back roads shape the rhythm of daily life. The Chesapeake Bay Bridge is the main connector to the Western Shore, and weekend traffic can slow. But once you settle in, you may find that you rarely need to cross it—everything you need is right here.

Locally, the back roads are scenic and draped with farmland, waterfront glimpses, and wildlife. Commuters and longtime locals know alternate routes and timing tricks, especially in summer.

5. Outdoor Recreation Is Everywhere

Love being outside? You’re moving to the right place.

Popular activities include:

Boating and sailing
Kayaking and paddleboarding
Fishing and crabbing
Biking on scenic trails
Birdwatching (the region is a migratory bird hotspot)
Hiking through wildlife refuges
Golfing on award-winning courses

The Eastern Shore lifestyle blends nature with everyday life—expect to spend more time outdoors than you do now.

6. The Food Scene Is Better Than You Think

Seafood lovers, get ready.

The Eastern Shore is synonymous with:

steamed blue crabs
rockfish
oysters
crab cakes
farm-to-table produce

But beyond seafood, you’ll also find top-tier bakeries, craft coffee, upscale dining, wineries, breweries, distilleries, and seasonal farm stands.

Easton and St. Michaels, in particular, have made names for themselves in the regional culinary scene.

7. Housing Options Are More Diverse Than Expected

From historic brick townhomes to sprawling estates and contemporary waterfront builds, the Shore offers a surprisingly diverse housing market.

Common housing types include:

Waterfront luxury homes
Downtown historic homes
Modern estates on acreage
Golf course communities
Affordable starter homes
New communities designed for remote workers
Rural properties with barns or outbuildings

Working with a local agent matters, because pricing can vary significantly based on proximity to water, historic districts, and renovation potential.

8. Schools, Healthcare & Services Are Strong

Families moving to the Eastern Shore often ask about schools and healthcare.

Good news: the region benefits from strong public and private options, including:

Blue Ribbon public schools
Top private academies
Washington College (Chestertown)
Shore Regional Health hospitals & urgent care centers

While you may need to travel for specialized services, day-to-day care is excellent and accessible.

9. Expect Four Beautiful Seasons—and a Mild Winter

While Maryland experiences all four seasons, the Eastern Shore has milder winters than the Western Shore thanks to the Bay’s influence.

Expect:

warm, breezy springs
hot summers perfect for boating
gorgeous fall foliage
light to moderate snow in winter

Waterfront homes may experience more humidity or breezy conditions, but most residents love the year-round climate.

10. Community Matters More Here—Get Involved Early

If there’s one thing new residents consistently mention, it’s the strong sense of community. Neighbors know each other, local businesses are supported, and civic engagement runs deep.

Opportunities to get connected include:

Rotary and Lions Clubs
Yacht clubs and boating groups
Historic preservation societies
Volunteer fire departments
Arts councils
Church and community groups
Local festivals and charitable events

The more you participate, the more quickly the Eastern Shore will feel like home.

Ready to Make the Move? We’re Here to Help.

Relocating to Maryland’s Eastern Shore is more than a change of address—it’s a lifestyle transformation. With its scenic beauty, rich culture, and warm, welcoming communities, it’s one of the most rewarding places to call home.

If you’re ready to explore homes, understand local markets, or schedule a personalized relocation consultation, the experts at Coldwell Banker Chesapeake are here to guide you every step of the way.

Your new life on the Eastern Shore is waiting.