Photograph by Edwin Remsberg
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Steamed crabs by the bushel are a Maryland tradition.

Photograph by Edwin Remsberg

Road Trip: Maryland's Eastern Shore

Maryland’s Eastern Shore offers up-close encounters with skipjacks, blue crabs, and wild ponies.

From the September 2011 issue of National Geographic Traveler

An intimate place where land and water intertwine” is how author William Warner describes the marshy flatlands and scalloped coastline of Maryland’s Eastern Shore in his ode to the Chesapeake Bay, Beautiful Swimmers.

Driving rural Eastern Shore routes is a means of time travel, with retro snapshots at every turn—small-town Main Streets, chicken barbecues at the firehouse, fishing boats tethered to salt-weathered docks, and roadside farm stands with honor boxes among golden fields. Not just about nostalgia, the Eastern Shore is also a place to recharge and unwind, to take life at a slower, more mindful pace.

Start in Maryland’s capital, Annapolis, 50 minutes from Washington, D.C., via Route 50. Dubbed the “Sailing Capital of the World,” this harbor town, with its federal architecture and lively shops, restaurants, and galleries, is home to the U.S. Naval Academy.

Wander the gardens at the Paca Residence, the colonial-era manse of Declaration of Independence signer William Paca. Restoration architects and landscapers re-created the tiered terraces and parterres based on archaeological excavations and a portrait of Paca with the gardens as a backdrop. Look out for the heirloom roses, fish-shaped pond, and Chinese Chippendale bridge.

At the city dock, catch a water taxi to Back Creek, a couple of licks of land over, for lunch alfresco at the Back Porch, the quintessential yachtsman’s spot with a sweep of sailboats lined up at the marina.

From Annapolis, continue on Route 50 over the Bay Bridge and across Kent Island—largest in the Chesapeake Bay—to St. Michaels, a former shipbuilding town dating to the mid-1600s with elegant Victorian homes shaded by gracious old magnolia trees. Feel familiar? Owen Wilson’s 2005 romantic comedy Wedding Crashers was filmed here.

For all its polish, St. Michaels hasn’t forgotten its seafaring, oyster-shucking history. The sprawling Chesapeake Bay Maritime Museum (housed in ten waterfront buildings) wows with its screw-pile lighthouse on stilts and its interactive exhibits. See boats being restored, meet working watermen, and haul up a surprisingly heavy net full of crabs. Consider taking a two-hour, hands-on sail (with advance reservation) on the H.M. Krentz, berthed at the museum. The single-masted skipjack, originating on the Eastern Shore as an oysterman’s boat, had its heyday in the 1890s. America’s last commercial fleet under sail remains in the Chesapeake Bay.

Or stay on land to explore the shops of St. Michaels: Ophiuroidea has sea-inspired home goods like a surfboard-shaped serving tray; Hype is known for its eco-totes and sleek jewelry; Flamingo Flats offers sauces and seasonings for a crab (or shrimp) boil.

Take Route 33 west out of St. Michaels, and head south on Route 579 past secluded coves to the waterfront haven of Neavitt. (Look for the tongue-in-cheek street sign, “Almost Neavitt,” just as you pass a small cemetery.) Stop at the town dock overlooking Harris Creek to listen to the gentle slap of water on the wooden pilings.

Backtrack to Route 33 heading east to the well-manicured town of Easton, where Bartlett Pear Inn awaits. Dine on inn-made pâté and a salad of heirloom tomatoes and local ricotta in the dining room headed by chef Jordan Lloyd, alum of New York’s Per Se and D.C.’s Citronelle. Savor a nightcap on the second-story porch to a lullaby of the soft staccato of crickets, occasional whir of passing cars, and squeak of your rocking chair.

Breakfast on the fountained patio, then take a walking tour of Easton’s pocket-size downtown. Admire the restored 1930s art deco theater, a lively year-round hub of concerts, plays, and films, and indulge in a malted at the soda fountain at Hill’s Pharmacy, which dates to 1928.

Back on Route 50, head south toward Cambridge and James Michener country. To research his epic novel Chesapeake, Michener explored dozens of coves on the Choptank River by helicopter and boat. He’s among several notable writers who have lived and worked on the Eastern Shore, including Edgar Allan Poe, John Barth, and Christopher Tilghman.

In downtown Cambridge, get in touch with the culinary side of the Chesapeake at Jimmy and Sook’s, a small dining room filled with watermen’s tools and old photos and known for its raw bar, fried oysters, and soft-shell-crab sandwiches.

Rent bikes at Blackwater Paddle and Pedal on Bucktown Road, then head to Blackwater National Wildlife Refuge to spot bald eagles and ospreys. Miles of hiking and biking trails, at times on narrow wisps of land flanked by water and tall reeds, weave through 27,000 acres of tidal marshland and loblolly pine forest.

Reward an afternoon of cycling and hiking with pampering at the Hyatt Regency Chesapeake Bay Golf Resort overlooking the Choptank River in Cambridge. Book a hot tiger-shell massage at the spa, or take a dip in one of three swimming pools. For dinner, double back to the tiny town of Trappe, where chic Mitchum’s serves farm-to-table sides and prime steak cuts. Back at the hotel, wind down the night with s’mores and stargazing around a massive outdoor fireplace.

Next morning, you could linger at the resort playing a game of Frisbee golf or renting a Hobie Mirage, a trendy kayak-sailboat hybrid. Or head east toward Salisbury, home of the Ward Museum of Wildfowl Art, with its impressive collection of decorative and antique decoys.

A drive on the Eastern Shore wouldn’t be complete without a feast (or two) of steamed blue crabs. Try the delicate crustaceans at the Red Roost, a former chicken coop 40 minutes southwest of Salisbury. (The local steamed corn and fried chicken are fabulous too.)

Return to Salisbury, then amble east through quiet towns and farmland along scenic Route 346 until it meets Route 50. Follow 50 to Route 611 over Verrazano Bridge, which links the Eastern Shore and Assateague Island. Same as the famous New York bridge, this far more modest span is named for Italian explorer Giovanni da Verrazano, who is said to have passed these shores in 1524.

If you’re lucky, the wild ponies of Misty of Chincoteague fame will hold court when you arrive on the tranquil barrier island of Assateague. Though the roar and kitsch of bustling Ocean City is just across the inlet, Assateague’s undeveloped expanse of windswept dunes and tall sea grass is all about swimming, shelling, beach camping, and evening bonfires by the sea.

Breathe in the salt spray of the Atlantic. Wiggle your toes in the sand. As weekending Baltimoreans say about these parts, you’ve finally arrived “down the ocean.”