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.
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.
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.)
