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The Weekender: St. Michaels, Maryland

Where to eat, drink, and sleep in this historic locale on Maryland’s Chesapeake Bay

New England’s charm is perhaps best embodied by its quaint, coastal pockets frozen in time. On Maryland’s mid-state shorelines, the towns that dot Chesapeake Bay are a collective haven for scenic views, Americana hospitality, and some of the country’s best seafood, and St. Michaels is no exception. The historic town’s crown jewel comes in the form of a sprawling inn at the end of a picturesque main drag–after hanging your hat at the Inn at Perry Cabin, here’s how to make the most of a weekend getaway both on and off property.

Inn at Perry Cabin

Inn at Perry Cabin

Where to Stay:

The Inn at Perry Cabin has it all–from its impeccably appointed guest rooms and a Pete Dye-designed golf course on the water to some of the best sailing in the area, world-class dining, peaceful pool time, and much more, there’s plenty of reasons to stay on the grounds throughout your visit to soak it all in. Originally built in 1816, the former manor house has seen quite a bit of history and faces in its various iterations, perched upon its idyllic plot of land (among the original grants from England). At first, the site was a private home, then a tobacco farm, and a riding academy after that, and in 1980, a local family overhauled the property into a small hotel and restaurant. In 1989, the Inn at Perry Cabin was expanded from six to 41 rooms, and a recent $17M expansion and facelift transformed it into the striking estate we know it as today. Its rich history, of course, is an important element of the experience, and there’s no shortage of subtle reminders around the grounds.

Inn at Perry Cabin

Inn at Perry Cabin

Outside of the property’s perfectly manicured confines, the charms of Talbot Street (the town’s main–and very walkable–thoroughfare) and its neighboring waterfront are a mere bike ride or stroll away. The best of both worlds is at your fingertips, especially if you’re a fan of mom-and-pop shops, antiques, and freshly caught seafood.

Where to Eat:

Stars Restaurant, located inside the Inn at Perry Cabin, is an ode to Chesapeake Bay with its unparalleled views and hyper-local fare from the water and its neighboring farms. For a more casual dining experience on property, check out Purser’s Pub, a fireside eatery with great cocktails and local beers, or the High Tide Pool Bar (weather permitting). If you’re venturing into town, head to The Crab Claw, a local seasonal favorite for no-frills seafood since 1965, 208 Talbot for coastal new-American fare with plenty of gluten free and vegetarian options; for a sweet treat or coffee break, Gluten-Free Bakery Girl, Justine’s Ice Cream Parlour, and JoJo’s Cupcakes & Cream are all excellent choices on Talbot. Lastly, for the oenophiles, St. Michaels Winery (also on Talbot Street) is worth a visit for a tasting or to stock up on bottles for your stay.

Cuisine at Inn at Perry Cabin

What to Do:

You’ll certainly stay busy during your visit to St. Michaels (or at least as busy as you’d like to, given the endless opportunity to relax at the Inn at Perry Cabin). At the hotel, guests can take up tennis, hit the links, or sail across the bay; yoga and other wellness classes are also available, and for further relaxation, make an appointment at the spa (one of the very best in the area). Wine lovers are in for a treat with the Wine Judgement of St. Michaels tasting experience, modeled after the storied Judgement of Paris wine competition in 1976, hosted on property on a regular basis.

Inn at Perry Cabin’s private docks and yachts

Again, a tour of the town by bike or on foot is a must––antique shops and more await on Talbot Street and beyond, along with the 18-acre Chesapeake Bay Maritime Museum on the water as well as Eastern Shore Brewing (one of the oldest breweries in the area) and Maryland-made Lyon Rum’s tasting room and distillery just behind it. Let’s just say you won’t go thirsty around here.