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Maryland Cities and Regions


Maryland’s largest city is a genuine port town and centers almost exclusively around its bustling harbor. Though the handsome, red-brick Inner Harbor area may be touristy, it is home to a number of superlative restaurants, lively taverns, and shops, as well as the kid-friendly Maryland Science Center and the National Aquarium, where you can see sharks and sting rays. From here, take a water taxi to Fort McHenry to sing “Oh say can you see” at the battle site that inspired Francis Scott Key to write “The Star Spangled Banner” during the War of 1812.

The Eastern Shore

Going east from Annapolis via Route 50, visitors will cross The Bay Bridge over the Chesapeake Bay into Maryland’s “Eastern Shore,” which encompasses all of the flat coastal plains from Chesapeake Bay to the Atlantic Ocean. Here, 17th-century, picturesque towns like St. Michael’s, Cambridge, and Easton, as well as Kent Island in the bay, boast homey country inns, waterfront resorts, quaint bed and breakfasts, and a plethora of antique shops and flea markets. The Bay defines the pace of life here and, depending on the time of year, you’ll see waterman unloading bushels of blue crabs (June-September), soft shell crabs (April-June), oysters, and rockfish (September-December for both) in the town’s marinas. Farms and coastal marshland stretch for miles, making it the ideal getaway for a weekend a weekend sailing or antiquing.

Western Maryland

West of the Chesapeake Bay, Maryland’s main draws are the Blue Ridge and Allegheny mountains and Deep Creek Lake, a four season resort region at the headwaters of the Potomac River basin. In the summer, outdoor enthusiasts flock to the mountains, rivers, and lakes of Western Maryland to get out of swampy D.C (even the president’s “Camp David” retreat is located in the stumpy Blue Ridge hills). In the fall, the historic C&O canal draws bikers and hikers to its picturesque tow path along the Potomac for viewing pastoral autumn colors. If it’s well-kept beaches and port cities you’re after though, you’ll have to head to Eastern Shore (the Western Shore is far quieter by comparison).


Located at the conflux of the Chesapeake Bay and Severn River, Maryland's state capital is serious about sailing. Annapolis is home to the United States Naval Academy and hosts annual world class sailing regattas (August-September). Even the cobbled colonial streets are made from the ballast of old sailing schooners from the 18th and 19th centuries. Two Annapolis musts: getting out on the water and soaking up the historic, colonial ambiance of the Maryland Statehouse district.

Ocean City and Assateague Island

Hit the surf and sand in the seaside resort town of Ocean City. Located on the Atlantic Coast of Maryland's Eastern Shore, Ocean City has a reputation both as a family destination and a local summer party spot. The town's 2.7 mile boardwalk, dating to 1902, is lined with arcades, five and dimes, family amusements, and saltwater taffy vendors, not to mention blocks of outdoor clubs and bayside bars. Nearby, Assetuage Island National Seashore is home to miles of undeveloped beach and wild ponies, believed have originated from a shipwrecked 18th-century Spanish galleon.

Southern Maryland

On the Western Shore south of the D.C. sprawl, the counties of Calvert, Charles, and St. Mary’s are bounded by the tidewaters of the Potomac River and the Chesapeake Bay and infused with a colonial, southern feel. The marshy region’s seafaring heritage is evident in its many commercial fisheries, canneries, and shipyards. Make a trip to this secluded Maryland backwater for dockside oyster houses, calm and secluded Chesapeake Bay beaches, scenic lighthouses, and rolling tobacco plantations.

Capital Region

This northerly, central region contains all of the suburban sprawl south of Washington, D.C. Don’t be turned off by the word “suburb” though – the towns of Bethesda, Silver Spring, and Chevy Chase are each alluring in their own right. In terms of shopping and dining choices, these municipalities offer big-city diversity combined with small-town charm, making them great places to stay near downtown D.C.

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