Explore Annapolis and Ocean City, Maryland

Annapolis, Maryland

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You may know bustling Annapolis is home to the U.S. Naval Academy and Maryland’s capital, but if you’ve never been, you might be surprised at its rich history. The Maryland State House has the honor of being the oldest state capitol in continuous legislative use — and was once the nation’s capitol building. George Washington resigned as commander in chief of the Continental Army in this building in 1783.

After a visit to the Naval Academy, be sure to spend some time walking along the City Dock. Stroll past art galleries, pubs, fashion boutiques, and gift shops. The highlight is “Ego Alley,” named for the parade of expensive and remarkable yachts that sail past this waterfront walkway. Depending on the time of year, you might catch a festival, concert, or boat race here. For more history, check out the Banneker-Douglas Museum, Maryland’s official African American heritage museum. The Annapolis Maritime Museum is another noteworthy choice with an optional boat trip out to tour the historic Thomas Point Shoal Lighthouse. You can’t leave Annapolis without feasting on world-famous Maryland blue crabs, either steamed, fried soft shell, or in crab cakes.

Ocean City, Maryland

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Head east out of Annapolis on Highway 50 across the Chesapeake Bay Bridge to Maryland’s Eastern Shore, and you’ll end up in Ocean City, a quintessential beach town with a three-mile, lively boardwalk. Get your adrenaline pumping on the historic Trimper’s Amusement Park rides, sample candy from iconic candy stores, and sip a craft beer at Backshore Brewing Company.

If you prefer a more serene experience, head about eight miles south on Route 611 to the north entrance of Assateague Island National Seashore. Famous for its herds of wild ponies and beautiful beaches, this 37-mile-long island’s ecosystem is so highly valued, three agencies manage it (U.S. Fish and Wildlife Service, National Park Service, and the Maryland Department of Natural Resources). Wild horses have lived here for hundreds of years, reportedly descended from shipwrecked horses in the late 17th century. This 48,000-acre island that spans into Virginia is a birdwatcher’s paradise, with a large variety of sea and land birds. The best way to see the diverse wildlife is by boat, so consider taking a boat cruise on the Assateague Explorer or a guided kayak tour.

If you plan ahead, you can apply for an over-sand vehicle (OSV) permit, which allows you to drive on parts of Assateague’s stunning beaches. You’ll need a four-wheel-drive vehicle, shovel, car jack, jack support, tire gauge, and a tow rope or chain. Camping is the only overnight accommodation in Assateague, so you can stay in Ocean City or in any of the small towns that dot the peninsula south of Ocean City. You can’t drive the entire length of Assateague Island, so you need to head back to the mainland and drive south on US-113 to US-13 into Virginia’s Eastern Shore.