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Chesapeake Perfect in Maryland

Crab comes in two forms in Maryland’s portion of the Delmarva Peninsula: cakes or steamed, shredded or whole.

Cakes in eastern Maryland shouldn’t have the breadcrumbs, eggs or peppers you might find to the west: crabmeat, sauce and spices — that’s it. Whole crabs are similar. They arrive on a tray and are nearly always red, dusted with Old Bay seasoning and with melted butter on the side, along with the mallet and paring knife that are your only assistance in liberating the fresh, succulent meat from its tight shell.

Though the regulated season for the state’s famous blue crabs runs from the beginning of April to the end of November, the obsession lasts year-round, with winter oysters offering but a brief palate cleanser. On Maryland’s Eastern Shore, it seems no matter where you go, life revolves around three things — the watermen, the waterfowl and the water’s bounty — and they all have one thing in common: the great brackish waters of the Chesapeake, the United States’ largest estuary.

There may be only a couple dozen water-covered miles that separate the peninsula from the rest of Maryland, but there might as well be hundreds. Before the Chesapeake Bay Bridge opened in 1952, the Eastern Shore was so isolated that it petitioned the Maryland General Assembly twice to become its own state, a sentiment so ingrained that its residents put up the proposal again in 1998.

Eastern Maryland today is frozen in time, thanks to excellent preservation of buildings from all periods of American history, and a place where time slows down to focus on the essential.


Chestertown may lie just a few dozen miles across the bay from urban Baltimore, but it seems centuries away. Outside of Annapolis, there’s nowhere else today in Maryland where you’ll find such a high number of 18th-century homes. To experience an arrival in Chestertown as Colonial traders would have, take a two-hour sail on the Sultana, a reproduction of a 97-foot schooner built in 1768 or, if pressed for time, tour the boat while it is anchored on the Chester River between sails.

One of the most pleasant ways to experience Chestertown is to simply take it all in slowly by foot along the planned main street — called High Street in the British tradition — running from the river to what was once the town square, with the main concentration of taverns and inns for commercial visitors. Washington College, founded in 1782 under Gen. George Washington’s patronage, retains the largest Georgian structures in Chestertown today. For orientation, groups should start with the Geddes-Piper House, a Federal-style house museum that also serves as home to the Historical Society of Kent County.

Small groups can enjoy an overnight visit to the 1700s at the painstakingly restored White Swan Tavern, which began its life as a tannery and still accommodates guests in the original one-room dwelling.

The Necks

Continuing down Route 50, where the small, nesting peninsulas of eastern Maryland’s Chesapeake shoreline are known as necks, Easton sits right on the main peninsula. As the unofficial capital of this part of the shore, it’s home to two of the area’s biggest events, the 50-artist-strong Plein Air Festival, which celebrates outdoor painting in July, and the Waterfowl Festival, which draws 20,000 wildlife art enthusiasts each November.

On the shore in St. Michaels, the 10-building Chesapeake Bay Maritime Museum offers visitors a chance to meet working watermen and try their hand at hauling crabs and other chores of the shore life. Very hands-on groups can try shaping bow stems and laying planks with a shipwright on many weekends through the museum’s Apprentice for the Day program.

Given its vibrant waterfront culture, it comes as no surprise that St. Michaels is home to one of the most beloved crab houses on the shore: the Crab Claw Restaurant. So close to the water you can throw your leftovers to the rockfish, the Crab Claw is a hands-on experience of a very different kind. Once you place your order, your selection of crabs arrives without fanfare — fork or dishware right on your tablecloth, along with a mallet and a paring knife with which to get to work. Always ask for the jumbos, if available, as they deliver the most meat for your hard work, along with a flavor that many locals insist is sweeter.

To wash it all down, St. Michaels has your group covered, whatever their preferred libation. In the historic mill, now home to the Eastern Shore Brewery, groups can sample rotating beers like Buffelhead Brown, Duck Duck Goose Porter and St. Michaels Ale, and wine lovers can head next door to quaff Maryland-grown chardonnay and merlot at St. Michaels Winery. For something stiff, the Lyon Distilling Company, the state’s second legal distillery, offers tours and tastings of its rums and whiskeys.