Best Chesapeake Bay, Assateague and Delmarva Beach vacations this summer

Chesapeake Bay – 

The Chesapeake Bay is arguably the MidAtlantic region’s greatest natural asset and favorite playground. The shoreline and tributaries of the Bay measure 11,864 miles of scenic beauty, encompassing a huge section of Virginia’s and Maryland’s eastern coastline. To compare this incredible fact, consider that the Chesapeake coastline is longer than the entire west coast of the United States. 

Lovingly referred to as the Eastern Shore, the Bay is dotted with quaint villages and a few medium-size cities. Many of these population centers were founded and developed as seafaring economies in pre-Colonial times. During the summer months, Bay towns swell with visitors in seek of cool breezes and abundant water activities, and they are sanctuaries for recreation enthusiasts who enjoy boating, fishing, kayaking, crabbing, waterskiing, paddle boarding, sailing and jet skiing. 

Spending time in or beside the Bay conjures an entirely different feeling from our busy day-to-day lives. Beachcombers, nature lovers, lighthouse devotees and history buffs all find enticements here. Some come to windsurf from the sandy beaches of Sandy Point State Park or commune with seabirds at Blackwater National Wildlife Refuge.

Terrapin Nature Park in Kent Island has miles of boardwalk for biking and hiking.

Many go boating around the coves of Terrapin Nature Park in Kent Island or ride the ferry to explore historic Smith Island.

Others make a pilgrimage to survey the path Harriett Tubman took, leading enslaved people to freedom on the Underground Railroad. The Harriett Tubman Byway winds through 125 miles through Dorchester and Caroline County, including the banks of the Choptank River.

The Harriett Tubman Byway winds through 125 miles. Visit the Harriett Tubman Visitor Center to learn more about the leader of the Underground Railroad.

You can take a scenic paddlewheel ride with Choptank Riverboat Company, or hop sightseeing pontoon on River Run Cruises departing from Matthew’s Landing. The Bay also serves as a thoroughfare for cruise ships leaving from the Port of Baltimore. 

The word Chesapeake comes from the Algonquin Indian name “great shellfish” which explains why the Bay is also ground zero for the best Mid-Atlantic seafood, especially the iconic blue crab. Standout towns worth investigating include Annapolis, St. Michaels, Chestertown, Oxford, Cape Charles, Cambridge, Havre De Grace, Solomon’s Island and Chesapeake Beach. Distance varies depending on destination, but Annapolis is one hour, and St. Michaels is 2.5 hours.

The lighthouse in St. Michael’s Harbor.

Assateague Island – 

Assateague Island ( is a remote atoll north of Chincoteague Island. This protected landscape is best known for the wild ponies that have survived in Assateague for centuries. Part of the Delmarva Peninsula, the protected barrier island on the edge of the continent, feels very different from the nearby beach communities. 

Maryland and Virginia each claim a portion of Assateague Island. The landmass has been overseen and preserved by the National Park Service since 1965. The Virginia portion is accessed through Chincoteague Island and is home to The Chincoteague National Wildlife Refuge which was established in 1943. 

Sunset over the Chesapeake Bay.

Assateague has 37 blissful miles of coastline with picturesque sandy beaches on the Atlantic Ocean. Diverse habitats thrive inland including woodlands, marshlands and dunes. NPS Rangers offer programs in the warmer months on the unique environment and history of Assateague Island.

Watermen from the region “farm” the waters around Assateague Island in search of clams and oysters. Many visitors come to this National Seashore to watch the ponies, swim, surf, camp, bird watch, kayak and sunbathe. Kayak landing areas in Maryland are located across the bridge from the Assateague Visitor Center and by the Ocean City Inlet.

Check out the wild ponies at Assateague Island

The southern third of Chincoteague National Wildlife Refuge is located on Assateague Island, and every July, the world-famous Pony Swim takes place where the wild horses are rounded up and the foals sold at auction. This process helps to keep herd numbers manageable and raise funds for the Chincoteague Volunteer Fire Company, the organization that owns the Virginia ponies. Another attraction in this area is Wallops Island, a NASA flight facility just south of Chincoteague. Drive time is about three hours. 

The historic town of Berlin, Maryland. The movies Runaway Bride and Failure to Launch were filmed here.

Delmarva – 

Delmarva is named for the peninsula that runs from southern Delaware, down the Maryland coastline, and then south along Virginia’s Eastern Shore. Each of the towns bordering the Atlantic Ocean has its own appeal and vibe. At the top of the peninsula are the Delaware towns of Lewes, Rehoboth Beach, Dewey Beach and Bethany Beach. Rehoboth and Bethany are especially family friendly with festive boardwalks, while Dewey is known for its live music and party atmosphere.

There’s world class fishing and boating around the Delmarva Peninsula. Rockfish and crabbing are the favorites among seafood lovers.

Historic charm and Cape Henlopen State Park have made Lewes a top destination. All are bounded on the east by the Atlantic Ocean and the west by Rehoboth and Indian River Bays. There are countless opportunities for seaside entertainment in these communities including kayaking, canoeing, jet skiing, windsurfing, paddle boarding, sailing and fishing.

Everyone loves a day at the beach. Especially at Rehoboth Beach and Ocean City.

Further south are the Maryland coastal towns of Fenwick Island and Ocean City. Ocean City is particularly popular, thanks to its 2.5-mile boardwalk, high rise condos, buzzy nightlife and world-class deep-sea fishing trips. Ocean City’s famous amusement park, located at the southern tip of the boardwalk, is nearly a century old and offers endless entertainment.

Further south, we travel to Virginia’s Eastern Shore. This more rural section of the peninsula is populated by hamlets like Wachapreague, Exmore and Cape Charles. At the south end, the 23-mile Chesapeake Bay Bridge-Tunnel crosses into Virginia’s Tidewater region and Virginia Beach.  

Beachcombing on the quiet shores of the Bay provide hours of relaxing entertainment.

There are countless water activities in Delmarva, as these communities were established to take full advantage of the rolling waves and endless beauty of the Atlantic Ocean. Along with surfing, boating, fishing and swimming, there are action-packed water parks like Jungle Jim’s in Rehoboth Beach, Thunder Lagoon in Fenwick Island, and Jolly Roger’s Splash Mountain in Ocean City, to name a few. Drive time to Ocean City is about three hours.

At Rehoboth Beach Funland. Woohoo!

For more information about a beach or Bay trip:

Assateague Island

Baltimore beaches Dog Friendly Travel family travel getaways Hiking Kid Friendly Maryland MidAtlantic Travel Travel Virginia Travel

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Freelance writer and photographer specializing in vivid, deeply reported stories about food, travel and family.

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