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Part of the U.S. state of Maryland
Photo: Jennifer Schmidt, Copyrighted free use via Wikimedia Commons
The Eastern Shore region is Maryland's part of the Delmarva Peninsula, which is shared with Delaware and Virginia's Eastern Shore. The area is rich in culture and history, making it a great travel destination for anyone who's looking to soak up the local culture!
By plane
The nearest major airports are: Washington Dulles International Airport (IAD), Reagan National Airport (DCA), Baltimore-Washington International Airport (BWI), and Salisbury-Ocean City Wicomico…
By train
- Union Station (WAS), North Philadelphia (PHN), and Philadelphia-30th Street Station (PHL). From these train stations you can take a bus to various cities on the Eastern Shore.
By boat
As of June 2026, there are no regular commercial ferries crossing the Chesapeake Bay, though there are some in the planning stages.
By foot
The Appalachian Trail goes from Maine to Georgia and 41 miles of the trail are in Maryland and the Chesapeake & Ohio Canal National Historic Park rails to trails route stretches from DC to Columbia.
By car
Unless you prefer to stick to the water when traveling, a car is an absolute necessity to have a good time on the Eastern Shore.
By boat
Ferries are available from Crisfield to Deal Island, Smith Island, and Tangier Island. Marina's are quite easy to come by for travelers with their own boat!
By bike
The region's relatively flat landscape lends itself well to bikers. There are multiple bike shops, and there's no shortage of scenic bicycle trails.
Choose an airport to see hotels, stations, taxi ranks and car rental desks around it.
Dover · Regional · DOV
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a historic town of 10,000 by the Bay Bridge, one-time home to Harriet Tubman, and Annie Oakley.
a town on the Chesapeake and Delaware Canal.
small historic town on the Chester River.
Denton is in Maryland, nicknamed "The Garden of America".
another historic town near the birthplace of Frederick Douglass.
a charming small town on the Bay, popular with boaters
pretty, historic small town, with nice boutique shopping.
historic, but gritty port town—the one-time seafood capital of the East Coast.
the popular beachside resort town, known best for its boardwalk and nightlife.
historic small town and county seat.
the largest city in the region.
several historic small towns
a true gem of the East Coast shoreline; a barrier island with a beautiful beach, wild ponies, and nature trails through the bayside wetlands.
the Great Shellfish Bay, and the source of Maryland's maritime and seafood culture.
a quiet collection of three tiny islands home to fishing communities and the historic Hooper's Island Lighthouse.
a pretty island off the Bay Bridge, home to historic Stevensville.
a watermen island long lost in time, with nary a car to its name.
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