Visiting this Chesapeake dreamboat is like stepping into a picture postcard—and having some fresh crab while you're there.

Eastern Shore of Virginia & Maryland
Credit: Mark Sandlin

Once a trading post on Maryland's Eastern Shore, St. Michaels has become one of scenic Talbot County's prized gems. Vacationers from nearby metro areas like Washington, D.C., and Philadelphia flock here for the gorgeous views, historic architecture, and died-and-gone-to-heaven seafood.

What the Locals Say

"The Chesapeake culture is alive and well in Talbot County," says Cassandra Vanhooser, director of economic development and tourism. After years of traveling the South as a writer for Southern Living, Vanhooser found a spot on the map she just couldn't leave.

"We can trace our roots back to the 1600s, but our coastal towns and villages are not stuck in yesteryear," she explains. "They are vibrant, thriving communities that combine modern amenities with Old World charm. Talbot County also draws an eclectic mix of individualists, from captains of industry to watermen (and women) who still make their living fishing for blue crabs, oysters, and rockfish."

Quirky Claim to Fame

During the War of 1812, residents supposedly fooled British barges, which had moved into the Chesapeake Bay, by dimming lamps in St. Michaels and hanging lanterns high in the trees beyond town. In the darkness of the wee hours, the Brits fired their cannons too high. The one house they definitely hit—now called ‘the Cannonball House'—sold for $1 million last year.

Dining Options Galore

"Everyone loves The Crab Claw Restaurant and the St. Michaels Crab & Steak House," says Cornelia Heckenbach, associate broker with The Long & Foster Christies Great Estates. (It was Heckenbach who successfully listed the Cannonball House.)

For fine dining, locals will point you to 208 Talbot, as well as Stars at the Inn at Perry Cabin by Belmond. (Stars is pricey, so go there for breakfast or lunch if you're on a budget.) Foxy's Harbor Grille is a popular bar known for its fish tacos, as well as drinks and atmosphere. Awful Arthur's Seafood Company has been serving fresh catch for more than 40 years and has a locally famous steamed seafood platter. Find hearty breakfasts and a lunch menu featuring such local faves as the crab vegetable soup and saloon burger at the Carpenter Street Saloon. Get a spectacular view from the covered port deck of Harbourside Grill, with a relaxed atmosphere and local beers and spirits. One more local favorite—Bistro St. Michaels.

We could go on and on because St. Michaels is a foodie's dream, with everything from fresh-off-the-boat seafood to Italian eateries, coffee houses, and inventive cafes. Click here for a list: St. Michaels Restaurants.


You'll find only a few rental cottages in St. Michaels because the town doesn't allow short-term rentals any more. Try the 20-room, adults-only Five Gables Inn & Spa (affordable), The Old Brick Inn (a splurge but doable), or the luxe Inn at Perry Cabin by Belmond (we're gonna need a bigger piggy bank).

Things to Do

Boating, paddling, fishing, swimming, biking—outdoor activity abounds in St. Michaels. You'll find plenty of shops and galleries in town, as well as St. Michaels Winery and Lyon Distilling Co. Stop by the Chesapeake Bay Maritime Museum, an 18-acre waterfront museum showcasing the Chesapeake and it people. In 2016, the museum began restoration of the 1889 Edna E. Lockwood, last remaining log-bottom bugeye under sail. They're hoping to relaunch the boat for the annual OysterFest in 2018.

So You Want To Live Here

"St. Michaels is a lovely small town with beautiful homes and gardens that are all very well maintained," Heckenbach says. "Some of our homebuyers are retirees who have lived on the water and decided to downsize. They like living in the village, where they can walk everywhere. But we also attract weekenders and young professionals. This is the kind of town where we speak to each other on the street and forget to lock our doors, and yet I can take the train into New York and come back the same day. The proximity to Washington, D.C., gives us international influences because everyone who moves here brings something to St. Michaels and gets involved. It's a very active community."

Buyers, she said, come for the water, the food, and the proximity to major metro areas. As for pricing? Outside the historic district, you can find homes in the 200s and 300s. Inside the district, expect 400s to 800s on average. And then there are those that go for $1million and up. Cannonball included.

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