The middle of November, with a brisk wind coming steadily off the Chesapeake Bay, might seem like a funny time to venture to the Eastern Shore of Maryland—an area known for its nautical culture and a slowed-down pace more usually associated with the warmer months. But I had recently moved to Washington, D.C., and with the kids in school and COVID—at that moment at least—relatively under control, I was in need of a drivable weekend away, the first I’d take with a friend in … a lifetime? It felt that way, at least, though I’d guess it had only been a very long three years.

More than a decade earlier, I had been introduced to the region by a friend who had grown up there—just about a 90-minute drive from metropolitan Washington, but from her descriptions of a childhood in a log cabin nestled amid a peach orchard, it seemed a century away. She invited me out to sail with a friend, and I was struck by the way he pronounced the name of his boat—like something lifted from the English Isles rather than these watery Maryland ones. (There is a theory that some islands in the region have actually retained the Anglo-linguistic remnants of their colonial past due to their relative isolation over the years—at the very least, the region has a distinct dialect imbued by a deeply entrenched, sometimes insular culture.) A few years later, I attended her wedding at Tilghman Island’s elegant and easygoing Wylder Hotel, a location that felt as though it was perched on the edge of the earth. I was charmed all over again.

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Sailboats participate in a sailing regatta on the Eastern Shore of Maryland during a warmer months.Steele Burrow / Aurora Photos

So my friend and I set off, despite the falling temperatures, encouraged by the fact that mid-November marks a festive bellwether as the start of goose-hunting season, with the Waterfowl Festival kicking it all off. (I’m not a hunter, but festivities are festivities!) Inaugurated in 1971, just two decades after the Chesapeake Bay Bridge opened up the region to a greater number of visitors, the festival showcases local artists and food (crab!) as well as some of the unique culture and traditions of the region.

The morning after our arrival, my friend and I made our way to Easton, where, on the periphery of town, a number of camo-clad participants in the popular Retriever demonstration were gathered around a lake. When the cannon fired, in the pups plunged, struggling adorably to return the dummy fowl to their owners. Was it a competition? A demonstration for day-trippers who didn’t know such a ritual existed? Hard to tell. Despite the intense focus of the owners, there seemed to be a spirit of general camaraderie more than competitiveness.

That spirit extended into town, where we walked the brick paved streets, in awe of the epicurean delicacies on offer at The Wardroom market and bistro and the wall of illuminated Marriage Freres tea tins at The Weather Gage, more like a Parisian cafe than a sleepy coastal town coffeeshop. The meticulous presentation in these two venues (as well as at a truly delightful bookshop, Flying Cloud, and several other venues in town) we later learned was the product of Bluepoint Hospitality—a consortium that wisely wooed the almost three-decade Le Bernadin Maître D, Ben Chekroun, from Manhattan to Maryland to act as general manager when the pandemic shuttered the New York restaurant.

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An interior at The Wildset Hotel in St. Michaels, Maryland.Maya Oren

Having had our fill of both fowl-themed entertainments and food, my friend and I made our way back to our hotel, the newly opened Wildset, in St. Michaels, where the kitschy nautical decor that’s a mainstay of St. Michaels’ many touristy shops has been stripped down in the spirit of Scandiwegian minimalism. With crisp white bead-board walls, Grown Alchemist products in the bathrooms, and slate-colored fireplaces set to blaze, each of the hotel’s 34 rooms (set across three buildings) is imbued with elegant simplicity and comfort. (Outside, along the town’s main street, the Christmas shops were kicking into gear; inside it was a sea of tasteful neutrals.) Later that evening, we were offered oysters from the Chesapeake at Wildset’s restaurant, Ruse, which opened, along with the hotel, just a few months ago and was already packed with patrons. A baggie of s’mores materials waited in the extremely well-curated Sundry and Coffee Shop at the front of the hotel, available for hardy patrons who wanted to brave the increasingly bitter winds and gather around the campfire at the rear of the hotel.

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Ruse Restaurant at The Wildset Hotel Maya Oren

The next day, I wandered out along the gingerbread houses and wooden docks demarcated with “Waterman Parking Only” signs. Streets that might be crowded in the summer months with history buffs were pleasingly sedate. Although St. Michaels’ history dates back to the 17th century, it gained its greatest notoriety in the 18th century, as “the town that fooled the British” in the war of 1812. Having been made aware that an attack was likely, the residents of the town elevated their lanterns on trees, causing the British to overshoot and miss their targets. It was sleepy and quiet and all the more delightful to watch the sun glinting off the water.

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The harbor at St. MichaelsMaya Oren

That evening, my friend and I walked down the street to The Inn at Perry Cabin, one of the more famous and established of the Eastern Shore’s accommodations. Recent-ish fame derives from its cameo as the setting for Wedding Crashers, but the Inn has a long and storied history. It was originally built by naval officer Samuel Hambleton, who served as aide-de-camp to Commodore Oliver Hazard Perry during the War of 1812, and who was rewarded by Congress for driving the British from Lake Erie with a parcel of land along the Chesapeake. He named the home he built on the property after his friend, Commodore Perry, and after a century or two as a working farm, it was eventually transformed into a riding academy then holiday destination. (Samuel Hambleton’s hidden staircase, obscured behind a bookcase in the Inn’s library, still functions as a quick getaway.)

The Inn at Perry Cabin
The Inn at Perry Cabincourtesy Inn at Perry Cabin
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A suite at the Inn at Perry Cabincourtesy Inn at Perry Cabin

Now a high-end resort, the Inn offers what might be the ultimate luxury—a “skip the bridge” service to reach it via boat in the warmer months and avoid the Bay Bridge traffic—as well as a host of other attractions: a Pete Dye-designed golf course, a spa that takes inspiration from its environs, a range of nautical activities, and of course a suite of sumptuous rooms in which to just relax. Since we were staying down the street, my friend and I did our relaxing at the restaurant, STARS, reinvented by Napa transplant Chef Gregory James to truly prize a sea- and farm-to-table ethic (most ingredients are sourced from within a 20-mile radius). At the end of our delicious meal, a duck-shaped glace fruit concoction appeared on our table as a farewell note to send us sweetly swimming into the night.

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courtesy Inn at Perry Cabin