As spring slowly tips into the flat heat of summer, it is prime time to head toward the beach. The fine news is that a refreshing breeze off the water may be closer than you think. Just over the Bay Bridge, and only an hour from Baltimore and Annapolis, lies Maryland’s Eastern Shore, where small towns are speckled with romantic bed and breakfasts and charming inns, and seafood is a way of life.
You will go over a bridge. Not the Bay Bridge, but a second, smaller one. You are then greeted by a long row of 1940s-era homes along Water Street, their docks built helter-skelter and fanning out from the shore into the tall sea grass and cautious waves of the inlet. You have reached Chestertown. Pass through the quiet, coastal streets to the other side of town and then head a little farther still to reach the Brampton Inn. The first impression of the bed and breakfast is that of history—of the long traditions in the Chesapeake Bay region, back when most of the Eastern Shore was wilderness, homes were made of clapboard, and plantations still thrived throughout the South. The antebellum construction that makes up the bulk of the Brampton is peaceful, even romantic, with huge porches, quiet reading rooms and libraries meant for losing track of time, and hushed passageways and stairwells where you might, every once in a while, come across another guest. Breakfast in the main house starts bright and early: farm fresh eggs, country ham, coffee, stacked blueberry pancakes drizzled with local maple syrup…if they have it in the kitchen or if it’s available, Chef will whip it up for you.
For an even more secluded retreat, opt for one of the Brampton’s private cabins. Built around the original standing outbuildings of the plantation, like the barn and tool shed, the spaces have been revamped for optimal luxury. A private entryway through the barn leads down a cobblestone path to the modern, sun-washed havens with kitchenettes, reading nooks, and vast fireplaces, which can be enjoyed even while reclining in the tub. A second screened porch reveals a Japanese soaking tub and an outdoor shower in a private courtyard, where guests can lounge au naturel with confidence that they won’t be disturbed. The fields surrounding the cottages extend for acres and acres of meadows and forest and are ripe for hiking and exploring, but guests can’t be faulted if they instead prefer to roam closer to home. For a truly blissful experience, don something light and linen and head for the hammock for an afternoon of uninterrupted reading under the soothing bayside sun.
The Inn at Perry Cabin by Belmond is the kind of place where early risers love to stay, not just because the Washington Post is delivered to the door by eight a.m. each morning and the private patios are perfect for those coffee-and-paper sessions, but more so for the views of the bay at sunrise. Out the window of the rambling colonial mansion, rooms open to a sprawling lawn littered with waterfowl and beds of roses, daffodils, and pansies, beyond which lie the marsh and the bay, where sailboats bend and skip in morning races. After coffee, head over to Linden Spa for some stress-relieving indulgence, then sash up your robe for a game of croquet out on the lawn. A stroll along the gardens and docks brings you around to the dining hall where a proud Maryland flag resides over a large fireplace, dinner is served in a setting of stately nautical details, and, if you’re lucky, the Eric Felten Trio is playing jazz and classics all night.
The food at Stars is rich, delightful, and executed with evident skill. A quick scan of the menu at Stars yields a refreshing lack of buzzwords. Nothing is highlighted as organic, farm-fresh, or artisan, and yet it’s all of the above. (When I ask if the oysters are local, the waiter’s look is almost quizzical. “Of course,” he says, “from about ten miles down the road.”) After oysters, order the foie gras (that is a directive, not a suggestion), especially if foie gras is done “au torchon.” The take on the three-day process, the foie is wrapped in a kitchen towel and soaked in milk and honey. The result is otherworldly…it might be better than butter. Lastly, cleanse your palate with something fine and old, either straight or on the rocks. But do stop after just one if you can. After all, you may want to be up early to catch that sunrise.
At the center of the small town of Easton, Maryland, is an inn that serves as the hub of its community. A grand brick building with tall ceilings and elegant architecture, The Tidewater Inn has hosted greats from Bing Crosby to the Kennedys. Now a popular wedding and convention destination, it is easy to see why The Tidewater has endured. Airy, light-filled rooms with classic, federal-style furniture, historic fireplaces, and ornate molding serve as a backdrop for events ranging from a meeting of local Amelia Earhart enthusiasts to the largest waterfowl conference in the United States. The hotel’s nearly one hundred simple, well-appointed rooms overlook intimate courtyards of posies and fountains, a cozy tented pavilion, and the quaint streets of Easton, lined with boutiques and local restaurants with nary a chain in sight. You’re in the ideal space to wander unobstructed, exploring neighborhood bakeries and a local art scene with little chance of getting lost. After wandering the afternoon away, stop by the Bannings Tavern, which you’ll know by its vintage marquee listing upcoming live music. Catch some coastal talent and down a few beers before heading back across the street to The Tidewater for dinner. On a tranquil spring afternoon, snag a patio seat and watch the locals mosey by at small-town speed, catching up on local gossip and going about their daily errands. If you’re looking for an authentic Maryland eating experience, Hunters’ Tavern is the place to order crab cakes or cream of crab soup. Filled with succulent, fresh lump crabmeat and served with saltines and a splash of sherry, the cream of crab soup here is simply Maryland in a bowl. But don’t stop at crab; if oysters are your thing, do try the Chesapeake oysters straight from the oven prepared in one of three ways: “Rockefeller” with spinach, bacon, and hollandaise; “Champagne” with Virginia ham, pistachios, and beurre blanc; or—what else?—“Baked Crab” with crabmeat, spinach, tomatoes, and feta.