How to Plan a Trip to Maryland’s Chesapeake Bay Country

Along the Atlantic coast of Maryland, between the ocean and the Chesapeake Bay, is a region that remains often unseen by travelers. This area, known to locals as the Eastern Shore, Bay Country, Across the bridge or Chesapeake Country. Whatever you call it, it means the part of the state untouched by big cities and wide highways. This area of the Maryland offers a simpler and more peaceful experience. This rural and picturesque area is a hidden gem and an outdoor lovers retreat. The quaint towns, gorgeous rivers and rustic vibes are the perfect escape from the city life that lies to the west of the Chesapeake. The unique charm makes Maryland’s Chesapeake Country a destination worth exploring. In this article, I will share the best that this area has to offer. 

Water Adventures on the Eastern Shore

This region of Maryland is surrounded by water. The Chesapeake Bay is a major part of the culture of the area. To the east, we have the Atlantic Ocean with miles of beaches. Throughout the rest of the landscape, a multitude of estuaries, streams and coves wind and curve through farmland. To really experience the Chesapeake, you have to get out on the water! 

Kayaking

Personally, my favorite way to immerse myself in a destination is to get on a kayak. I love kayaking on the Chesapeake Bay and its estuaries. There are so many opportunities to do it. Nearly every town has kayak outfitters, and some even have guided tours. You can find a peaceful cove, or you can head out to the bay for vast views and choppier waves. 

Boating

Another way to enjoy the water is by boat. You can book a boat for a full day or half day, with or without a captain. I love feeling the salty air blowing through my hair as we speed out into the vast waters of the Chesapeake. Spend your weekend fishing for bass or just enjoying the sun. A great bonus is getting out there early enough to see the sunrise on the water. There is truly nothing more beautiful than watching the sunrise on the bay. 

Blackwater National Wildlife Preserve

This Wildlife Preserve is a must-see destination for outdoor enthusiasts. Rent a kayak, or hike the marshy trails to get an in- depth look at the many species that call this area home. You have a good chance of seeing ospreys, bald eagles, deer and the region’s famous blue crabs. Stick around until sunset, because the views here are incredible. 

Visit The Atlantic Beaches

The Eastern Shore of Maryland is probably best known for its beaches. There are a handful of oceanic beaches, all with slightly different vibes. Growing up around here, you learn that everyone has their favorite for specific reasons. 

Ocean City

Ocean City, Maryland offers miles of sandy beaches and a vibrant boardwalk.  With family-friendly amusement rides and an entertaining nightlife, you can be sure everyone will find something to love. Ocean City is a quintessential beach getaway with a perfect blend of relaxation and excitement. I spent my summers here as a kid, and I can still smell the mix of salt water taffy with sun kissed sand. Its a magical place to go as a kid.

Rehoboth

Rehoboth, Delaware draws visitors for its sophisticated tranquility and seaside charm. This small beach town offers wide sandy beaches, unique boutiques and art galleries. At night, the boardwalk comes alive with fun energy and live music. When visiting this town, don’t forget to stop in a local eatery for some seafood. 

Assateague Island

Assateague Island National Seashore is a coastal marvel known for its abundant wildlife, oceanfront camping and unmatched beauty. Wild horses roam freely on the island and are surprisingly unbothered by visitors. There are no shops or hotels on the island, which makes it all the more appealing. Immerse yourself in natural beauty by hiking the trails and sleeping under starlit skies. This untouched paradise is a testament to the natural beauty of the Eastern Seaboard. 

I tent camped here and I was stunned with the amount of stars that were visible at night. Its really an incredible place to camp. In the morning, I was shocked to see the wild horses roaming through the campgrounds. They try to pick at the camper’s food, and are generally curious. If you only have time for one thing to do in Maryland, I think this should be it!

Visit Historic Eastern Shore Towns

Chesapeake Bay Country offers a welcome respite from the hustle of Central Maryland and the DC area to charming waterfront towns. You’ll find that each town is extraordinarily unique and varied. Everyone can find their favorite town based on their own preferences. 

Easton

Easton, Maryland is a timeless, beautiful town with historic streets and rustic charm. I love to walk along the cobblestone streets and see the centuries-old oak trees that are the pride of the town. The town square hosts lots of events, farmers markets and live music. 

Cambridge

This town is located on the Choptank River and takes pride in its waterfront location. The busy marina is bursting with energy as boats pull in with their catch of the day. You can grab a bite of freshly caught fish or crab at one of the local eateries. Their Main street showcases Victorian architecture with unique shops, art galleries and breweries. I usually have good luck fishing and crabbing at their docks, and I’ve even seen some Rays swimming in the water. Also, don’t forget to visit the Harriet Tubman museum. 

St. Michaels

This elegant waterfront town located on the Miles River is a must-visit destination. The center of town is a vibrant Main street filled with upscale restaurants, boutiques and galleries. Visit the Maritime Museum to learn about the region’s history. Kayak on their scenic cove and watch the sailboats coast into the marina. This town is slightly more upscale from the others, and the eateries and shops are a little more expensive.

Berlin

Berlin, Maryland is located inland of Assateague Island. This charming small town has earned the title “America’s Coolest Small Town”, with good reason. Stroll the charming Main street, visit the Mermaid Museum and explore the thriving local art scene. The quaint colonial architecture and tree-lined streets offer a backdrop to local festivals, events and farmers markets. 

Chestertown

This town, located on the Chester River, offers historic charm with its galleries, theaters and landmarks. Home to Washington College, this area has a lot of energy, pride and a rich heritage. 

Go Camping

I personally love camping on the Eastern Shore instead of staying in a hotel. With its quiet atmosphere, abundant wildlife and incredible view, it’s the perfect place to connect with nature.

 Janes Island State Park

A favorite of mine is Janes Island State Park. This Maryland park, located just outside of Crisfield, Maryland, is the perfect waterfront getaway. The campgrounds back up to Daughtry Creek with plenty of space for fishing, crabbing and kayaking at their marina. I love watching the sunset here, and talking to other campers. I always meet the nicest people here.

Assateague Island

Camping at Assateague Island should be on your bucket list, if it isn’t already. Pitch a tent, or park an RV at one of their many oceanfront sites. Wild horses roam freely on the island, and can be seen quite easily. Camp on a starlit beach and watch the sunrise over the Atlantic from your sleeping bag. It’s a surreal experience to say the least. 

Eat Seafood, of course

Maryland’s Chesapeake Country offers some of the most delicious seafood in the US. The pride of Maryland is blue crab, and you can’t visit without trying it. Order some steamed crabs from a crab house or try a crab cake sandwich. We have delicious striped bass that we have rebranded as Rockfish, oyster and catfish. You will, no doubt, find plenty of seafood restaurants to choose from on the Eastern Shore. 

Conclusion

The Chesapeake is a hidden gem of natural beauty, historic charm and adventure. Whether you’re visiting the beach or the bay, this region is a perfect destination for an outdoor lover.