This Charming Hotel in a Coastal Maryland Town Has Farm-to-table Dining, Yacht Charters, and Waterfront Views

Inn at Perry Cabin in St. Michaels, Maryland is a charming respite for city-dwellers looking to escape the grind for a weekend of waterfront relaxation.

The exterior of a suite at The Inn at Perry Cabin
Photo: Jason Varney/Courtesy of The Inn at Perry Cabin

Chef Gregory James bent down to pluck a piece of arugula off the plant. It was still soft and tasted mild, with a few hints of pepper.

We were standing in a greenhouse at Cottingham Farm, a 156-acre organic farm about 20 minutes from the charmingly quiet town of St. Michaels, on Maryland's Chesapeake Bay. A few hours later, James, the executive chef at Inn at Perry Cabin, would use that same arugula to compliment a seasonal farm-to-table lunch.

Dining at Inn at Perry Cabin
Courtesy of Inn at Perry Cabin

"I want people to question what kind of food they're [using to cook], and what [we're] doing to help impact the area?" James told me as I tucked into a salad of pickled beets and arugula — both from the farm — along with mini sandwiches seasoned, in true Maryland fashion, with Old Bay. "It really started with the garden. When I first got here, the garden was completely underutilized. It was there, it was pretty, but they weren't harvesting anything… and I was like, 'that's just a shame.' And so we started to utilize it."

Since coming to the Inn at Perry Cabin in 2019, James has made it his mission to shine a light on sustainability — and make it more than just a buzzword. He sources ingredients from within a 20-mile radius, introduces local producers to each other to grow the movement, and even partners with nearby Chapel's Country Creamery to age his own cheese using vegetable ash made from leftover herbs, scrubs, and flowers from his kitchen.

The hotel draws people in, offering locals and visitors alike a fine-dining experience unique to the area that is only enhanced by the surroundings: glowing fire pits lining the Miles River and picture-perfect gazebos framed by mature trees. Even breakfast at the property is indulgent with apple waffles liberally dusted with powdered sugar and made from apples grown on-site (there are more than 100 apple, peach, pear, and cherry trees on the hotel grounds).

But he's taking it a step further, cultivating farmland, which the hotel plans to open in 2022 as both a working farm and event space. The culinary focus compliments the hotel's other offerings, like it's sailing academy in which guests can learn to glide on the resort's fleet of Alerion Yachts. (Guests can also book the 55-foot Hinckley from Annapolis to arrive at the inn by boat.)

The hotel comes to life as the sun goes down, the casual Purser's Pub buzzing with a pre-dinner crowd enjoying a drink by a roaring fireplace before tucking in to James' multicourse menu at STARS. It's a different experience every night, he explained, thanks to a middle-of-the-day menu huddle and a meticulous focus on using the freshest ingredients possible, offering both an "earth-to-table" vegan menu and a "nose-to-tail" approach for everything else.

A fire pit at The Inn at Perry Cabin
Courtesy of The Inn at Perry Cabin
Interior of Purser's Pub at The Inn at Perry Cabin
Courtesy of The Inn at Perry Cabin

But beyond the top-notch food and elegant decor of the inn (famous for its part in the "Wedding Crashers" movie) lies the town of St. Michaels, itself a charming row of red brick-paved streets and mom-and-pop shops stocking sweater-wearing duck figurines and holiday decorations. The local pharmacy stands as a welcome throwback, full of knick-knacks and gifts like the tiny ornamental gold reindeer that now holds a proud spot on my bar at home.

Exterior and the docks at Inn at Perry Cabin
Jason Varney/Courtesy of Inn at Perry Cabin

Stroll down the quiet two-lane Talbot Street before making your way over to the waterfront Chesapeake Bay Maritime Museum where you can explore the area's history with boat building. Visit the latest exhibit, Dove Tales, set to open in April, where travelers can dig into a representation of the Maryland Dove, which brought colonists to Maryland in 1634.

And, finally, conclude your stay exactly as I did: I sat down to breakfast, savoring a fluffy omelet made with Chapel's Country Creamery cheese and peering out a large picture window at the waterfront as the tide gently lapped against the shore. It was a calm and peaceful Sunday morning in the mid-Atlantic, and I couldn't think of a more perfect place to be before the start of another busy work week.

Alison Fox is a contributing writer for Travel + Leisure. When she's not in New York City, she likes to spend her time at the beach or exploring new destinations and hopes to visit every country in the world. Follow her adventures on Instagram.

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