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  • In St. Michaels, Maryland, a Peaceful Seaside Getaway Awaits
Boats docked in St. Michaels
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In St. Michaels, Maryland, a Peaceful Seaside Getaway Awaits

The serene small town is rich with American history, elegant hotels, and waterfront activities.

By Erica Moody May 8, 2024 at 8:31 am

Eastern Shore Getaways: The allure of a slower pace calls. Discover the mystique of small Maryland and Virginia towns and find places where you can relax and unwind. This is where you’ll find superb seafood, adventurous shopping, and dozens of ways to connect with the region’s pristine natural beauty on land and water.

Drive time from Dulles: 3 hours

Take it from the parent of a toddler: St. Michaels is the place to get some quality rest. Wake in a water-view suite at the Inn at Perry Cabin (famous for its appearance in the film Wedding Crashers), where décor gives nautical vibes without a hint of kitsch, and enjoy fresh-brewed coffee and a Crab Imperial omelet courtesy of prompt room service on your private terrace overlooking the resort’s manicured grounds and the Miles River. It’s the picture of quiet luxury.     

The locals appear to be well-rested, too, particularly the ebullient tour guide Jay who leads the History of St. Michaels Tour, one of many activities organized by the Inn at Perry Cabin for guests. He’ll tell you the local legend of how the town earned the nickname “the town that fooled the British” during the War of 1812. One historic home, the Cannonball House, even displays the projectile that narrowly missed its residents. In another preserved home, the Dr. Dodson House, Frederick Douglass reconciled with his former enslaver Thomas Auld. More lore on Douglass, who was born in Talbot County and lived in St. Michaels for three years, can be discovered at the St. Michaels Museum.   

The long history of St. Michaels as a ship-building town is explored in the recently expanded Chesapeake Bay Maritime Museum, which holds an abundance of artifacts and vessels over its 18 acres and is located next door to the Inn at Perry Cabin. In fact, most things in this town of around 1,000 full-time residents are convenient. And, if you don’t feel like walking or driving somewhere, several hotels offer bicycles for guests. The Inn at Perry Cabin (rooms from $348 in low season and $554 in high season) takes it a step further and also provides complimentary car service to and from town throughout the day.      

If visiting in spring or summer, take advantage of the season and get out on the water. Book a cruise on one of Perry Cabin’s vessels for a luxurious experience. The Inn has seven, including the 1902 sloped skipjack, the Stanley Norman, which was added last year and is listed on the National Register of Historic Places. Options include the daily evening sail; at $130 per person, it includes a complimentary beverage and snacks, making it a perfect activity for a weekend with a group of friends. Private sails start at $600 for a two-hour excursion (ideal for an engagement or anniversary celebration). And even if you’re not staying at the Inn, you can still partake in the sailings. Want to learn the ropes? The Inn offers sailing classes. Love golf? Links at Perry Cabin is recognized as one of the best courses in Maryland. You can also get pampered at the spa, which offers hydrofacials, couples massages, and more, or simply relax on Adirondack chairs on the lawn and share ghost stories with your travel mates over s’mores by the fire pit.    

Take some time to browse the eclectic selection of stores along Talbot Street. Among the goodies you’ll want to take home: olive oils and vinegars at Olivins, collector ornaments at The Christmas Shop, hand-painted limoncello cups (and limoncello from Italy) at Simpatico, comfortable coastal attire at Chesapeake Trading Company, boho bracelets at Silva Wear, and nautical charts at Woodcraft Artisans.    

Summer Crush beer at Eastern Shore Brewing
Courtesy Eastern Shore Brewing

Where to Eat 

St. Michaels is not known for nightlife, but a party atmosphere can be found if you’re looking for it. At Carpenter Street Saloon, a true neighborhood bar, folks of all ages dance to live music, shoot pool, and sip orange crushes. At Eastern Shore Brewing, support local entrepreneurs by enjoying refreshing brews (the Summer Orange Crush is a seasonal standout) and conversation with friendly bartenders. And Foxy’s Harbor Grille fits the bill if you’re looking for a youthful, casual open-air vibe. For a cozy, romantic atmosphere, head to Bistro St. Michaels. For Italian, try the colorful Limoncello. For crabs, The Crab Claw offers views of St. Michaels’ harbor. And for ice cream, try Justine’s Ice Cream Parlour or take a drive to the Scottish Highland Creamery in Oxford. 

Where to Stay    

In addition to the Inn at Perry Cabin, the 34-room Wildset Hotel (rooms from $219 in low season and $279 in high season) will put you in the thick of the action, right in the center of town on Talbot Street. The hotel, which is spread across three historic homes, boasts stylish, modern flair. Its restaurant, Ruse, has a raw bar. Other options include boutique hotels like the Old Brick Inn and a host of bed-and-breakfasts, including the waterfront Victoriana Inn and the Parsonage Inn. 

Why Sea Glass Enthusiasts Flock to St. Michaels    

One person’s trash is another person’s treasure, the saying goes. Nowhere is that more apt that in the hunt for sea glass, the pieces of colorful glass and pottery found on the shorelines of waterways. The Eastern Shore is a hot spot for collectors to find gemlike sea glass, particularly a frosty blue variety. Hunting in low tide after a storm is known to be prime time to find it. If you’re not quite so daring, sea glass products can be found in local gift shops (Ophiuroidea “The O” on Talbot Street has a good selection of sea glass jewelry) and at the annual Eastern Shore Sea Glass & Coastal Arts Festival at the Chesapeake Bay Maritime Museum, with around 100 vendors showing off the colorful treasures. 

RELATED STORIES:

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  • 7 Eastern Shore Nature Preserves Perfect for Birding
  • Visit Wallops Island This Summer for a Glimpse into NASA’s Space Programs
  • Festivals and Events on the Eastern Shore You Won’t Want to Miss
  • Explore Easton, a Quaint, Walkable Town on Maryland’s Eastern Shore
  • How and Where to Find Eastern Shore Cruises in Maryland
  • Berlin, Maryland, Is Small in Size but Big in Character
  • Get to Know the Types of Virginia Oysters and Where to Find Them

Feature image, stock.adobe.com

This story originally ran in our May issue. For more stories like this, subscribe to Northern Virginia Magazine.

Erica Moody

Erica Moody

Contributing Editor

Erica Moody is Northern Virginia Magazine’s Contributing Editor. She has been a lifestyle journalist and editor for more than 15 years, with previous staff roles at Philadelphia magazine, Washington Life Magazine, and Travel Leaders Group. She’s consulted for brands including American Express Travel and Royal Caribbean. Her writing has appeared in Ad Age, The Telegraph, InsideHook, Technical.ly, DC Inno, and more. She holds an MFA from Antioch University and a BA from Tulane.

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