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Did you know there’s a New England-style destination right on Maryland’s Eastern Shore?

Named one of the “Top 10 Best Small Coastal Towns in America,” by USA Today and “Most Beautiful Town in Maryland,” by Conde Nast, St. Michaels is worthy of a weekend getaway or a romantic staycation.

In St. Michaels, Maryland, history surrounds you. Wander its preserved downtown, lined with gourmet restaurants, boutiques, and wineries. See beautiful federal and Victorian homes and old churches. Step back in time at a local museum then take in sailboat-filled harbor views at a local park. Or, simply have an orange crush overlooking a yacht-lined marina. 

Don’t forget about the incredible sunsets the Eastern Shore is famous for. Whether you do a little or a lot here is up to you. 

On a recent trip to this captivating Chesapeake Bay haven, we couldn’t help but fall in love with St. Michaels.

Here are some of our favorite places to see, dine, shop, and things to know before you go.

A bench and canon overlooking the marina at Muskrat Park in St. Michaels, MD.

Enjoy the view of the marina from Muskrat Park in St. Michaels, MD | Photo: Better Living

The History of St. Michaels, MD

The oldest town in Talbot County, St. Michael’s, dates back to the 1600s. In 1672, they named it after the first church started there, called the Christ Episcopal Church of St Michael Archangel.

After 340 years, the church continues to serve the community. Today you can visit the 1878 church on Talbot St in the heart of downtown St. Michael. Many of the headstones in its churchyard cemetery are from the 1800s. 

St. Michaels is on a peninsula and surrounded by two beautiful Chesapeake Bay-fed bodies of water.

The Miles River is the larger of the two and is to the west. On the river, you’ll find the Chesapeake Bay Maritime Museum, Muskrat Park, marinas, restaurants, and a few hotels. At Muskrat Park, enjoy live music on Thursday nights throughout the summer.

To the east of downtown is the quieter Broad Creek, perfect for kayaking. You can catch views of it from St. Michael’s beautiful Waterfront Park.

2 people kayaking at the marina in St. Michaels, MD

Kayaking in St. Michaels, MD | Photo: Better Living

Things To Do In St. Michaels, MD

St. Michaels is easy to explore in a day! Its downtown and most points of interest are all within a ½ mile radius.

Most shops and restaurants are found along Talbot Street. For more time to browse shops and relax, plan for at least 2 days. It’s a great place to bring your bike too. Rentals are available, but some hotels like the Wildset offer bikes free to guests.

St. Michaels earned the proud title of “The Town that Fooled the British.” It’s even displayed on the town sign as you drive in.

Legend has it that during the War of 1812, the people of St. Michaels learned the British were sailing into the Miles River. They were getting ready to attack the famous shipbuilding town.

The locals forged a plan. They placed lanterns high in trees so the British would overshoot and miss the town with their cannonball fire. The plan worked, and the British only struck one house, known as the Cannonball House. A private residence, it still stands today.

People have been summering in St. Michael’s since the 1880s. With plenty to do, see and eat, it continues to be a haven for travelers. 

Stroll downtown and shop one of the many unique clothing, home décor, or jewelry boutiques. Or get inspired at an art gallery.

Drink a crush cocktail, indulge in crab everything, sample local raw oysters, have a slice of Maryland’s famous Smith Island Cake and a gourmet coffee at Skipjack’s St. Michaels, or cool off with a sundae from Justine’s Ice-Cream Parlour

For some imported Italian specialties like gourmet pasta, condiments, home goods, and Italian wines, head to Simpatico. Then pop into Olivins for an olive oil and vinegar tasting.

For adult friendly beverages, try locally brewed beers at the award winning Eastern Shore Brewing or St. Michael’s own distilled rum at Lyon Distillery. Wine lovers can try locally grown and produced wines in the tasting rooms at St. Michael’s Winery or Bordeleau Winery across the street. 

Nature lovers can relax in one of the many parks, or hike or bike the easy 1.3 mile St. Michael’s Nature Trail that takes you through a covered bridge in Waterfront Park where you can catch stunning views of Broad Creek.

Those wanting to get out on the water can book a local cruise, or rent a kayak to explore the coast.

A woman walks down Talbot Street in St. Michaels Maryland

Stroll down Talbot Street to visit the many shops in St. Michaels. | Photo: Better Living

Walking through the streets of St. Michaels, you’ll feel as if you’ve stepped back in time. For a more immersive experience, head to one of the local museums.

Nautical lovers must visit the 18-acre waterfront Chesapeake Bay Maritime Museum where you can tour the historic 1879 Hooper Strait Lighthouse, and learn more about the region’s oystering and maritime history. Tour an active boat restoration in the working shipyard, or book a guided cruise on the Miles River.

St. Michael’s Museum features exhibits and walking tours of what life was like here centuries ago. You’ll find it in a charming 19th-century home on historic St. Mary’s Square.

Don’t miss their exhibit dedicated to Frederick Douglass, who spent a few years in St. Michaels. Once an escaped slave, he became one of the most important American activists, abolitionists, authors and state leaders in U.S. history.

Check out the Classic Motor Museum for their collection of classic automobiles, mid-century muscle cars, vintage trucks, and motorcycles on display.

Products for sale in the front of Antiques on Talbot in St. Michaels, Maryland.

Antiques on Talbot in St. Michaels, MD | Photo: Better Living

Treasure hunters wanting to take a piece of the past home with them will have fun visiting the antique shops in town.

Visit Antiques On Talbot next to the Wildset Hotel (look for the blue canoe). It’s a small antique shop, with everything from decoys, old oyster plates and cans, to cannonballs, jewelry, coins, silver, pottery, art, glass, furniture and more. 

Along with a unique find, don’t be surprised if you also leave with some incredible local travel tips.

The front of The Wildset Hotel in St. Michaels, MD.

The Wildset Hotel in St. Michaels, MD. | Photo: Better Living

Where To Stay in St. Michaels, MD

For a St. Michaels getaway, book a room at the recently opened Wildset Hotel. Casually luxurious and ideally located, Wildset is quickly becoming a favorite place to stay in St. Michaels.

The Wildset Hotel

Choose from 34 serene, and spacious suites in 3 completely renovated 19th-century buildings. With modern farmhouse décor and Scandinavian vibes, each suite here is unique.

All rooms have Parachute bedding, Grown Alchemist bath products, and Bose Bluetooth speakers. Some have premium features like fireplaces, balconies, and soaking tubs.  A bedside sound machine. complimentary snacks and bottled spring water are a welcome touch.

Room 102 at The Wildset Hotel in St. Michaels, MD.

Room 102 at The Wildset Hotel | Photo: Better Living

The king bed and open patio door of room 120 at The Wildset Hotel

A beautiful morning at The Wildset Hotel. | Photo: Better Living

At the heart of the property, Wildset’s two-story 1871 main building is home to its reservations area and Sundry shop. Grab an espresso, snack or pressed juice while browsing their chic collection of cookbooks, bags, candles, pottery and botanical apothecary items. 

In the mornings, a complimentary light breakfast is served. We loved the locally baked croissants with raspberry jam, mini quiches, fruit salad and lemon yogurt. Annapolis based Ceremony Coffee will perk up your morning.

Multiple bikes in a rack at Wildset Hotel.

Guests at Wildset can borrow a bike to explore St. Michaels. | Photo: Better Living

The free Wi-Fi at the Wildset Hotel will keep you connected. But everything here invites you to disconnect. By day, take off on one of their free-to-use cruisers to explore. For dinner make sure to dine at their incredible, onsite modern American seafood restaurant, Ruse (See our full review below)

Then at night take your complimentary s’mores kit to the fire pit and mingle with other guests under the stars. Well-behaved dogs are welcome.

A hand holding s'mores in front of the firepit at The Wildset Hotel

The Wildset offers free s’mores kits and a nightly firepit. | Photo: Better Living

Guests of the Wildset Hotel around the firepit in St. Michaels, MD.

The firepit at The Wildset Hotel | Photo: Better Living

 💡 Tip: Grab a bike from the hotel and cruise the nearby 1.3 miles St.Michaels Nature Trail.

Where to Eat in St. Michaels

St. Michaels has many wonderful places to eat! From taverns and chic downtown bistros to waterfront restaurants with gorgeous views serving Maryland favorites like lump crab cakes and raw oysters, there are great restaurants with friendly service waiting to be discovered.

Here are a few of our favorite spots to eat while in town.

A plate of roasted oysters at Ruse

Roasted local oysters at Ruse in St. Michaels, MD | Photo: Better Living

Ruse at The Wildset Hotel

209 Talbot St. St Michaels, MD 21663

Want a perfect meal at a restaurant from beginning to end? Go to Ruse at the Wildset Hotel. Named in honor of the town that fooled the British, Ruse’s modern American menu offers creative infusions of international flavors mixed with locally sourced ingredients. And seafood is the star of the show.

For an appetizer, the Crab and Ramp Rangoons served with a sweet and sour dipping sauce were crispy and delicious. And don’t miss the Local Roasted Oysters with roasted garlic breadcrumbs, Parmesan, and urfa biber (a smoky dried Turkish pepper). They’re buttery, salty and will have you licking the shell clean.

Seared jumbo scallops with greens and roe at Ruse

Seared scallops with local pea puree and smoked trout roe at Ruse | Photo: Better Living

For a perfect light dish with fresh flavors, try the seared scallops with local pea puree and smoked trout roe. Ruse’s Lemon Tart for dessert is sweet, creamy and tangy perfection.

Ruse’s simple but warm and sophisticated décor and welcoming service will invite you in, but it’s the food that will have you coming back again and again. When the weather’s fine, sit out on the patio under the twinkling lights as you take in a famous Eastern Shore sunset.

It’s my new happy place. And after a few bites, it will be yours too.

Ruse serves dinner and brunch.

Chinese Chicken Salad at Carpenter St. Saloon

Chinese Chicken Salad at Carpenter Street Saloon | Photo: Better Living

Carpenter Street Saloon 

403 South Talbot Street, St. Michaels, MD 21663

If you find yourself hungry in the center of St. Michaels, Carpenter Street Saloon, serves up seriously good down-to-earth food for breakfast, lunch and dinner. And this 1887 historic tavern setting with a full bar is a friendly local favorite.

Here you can order up made-from-scratch, soups, burgers, sandwiches, wings, fried oysters, and crabby fare like crab balls, crab dip and jumbo lump crab cakes. For something light, try the fresh and flavorful Chinese Chicken Salad with ginger honey dressing.

After you’re done, head upstairs for a game of pool in their game room.

Seared rockfish at Bistro St. Michaels

Seared Rockfish at Bistro St. Michaels | Photo: Better Living

Bistro St. Michaels

403 S Talbot St, St Michaels, MD 21663

For upscale French dining with Southern and international twists, Bistro St. Michaels offers a wine bar and exceptional food in a historic home in the heart of downtown St. Michaels. Fresh, local and seasonally inspired anything you order here will be wonderful.

Shrimp & Grits at Bistro St. Michaels

Shrimp & Grits at Bistro St. Michaels | Photo: Better Living

Some of our highlights include the classic French Onion Soup made with fresh herbs, and the Buffalo Shrimp & Grits appetizer, with unbelievably creamy grits and perfectly grilled shrimp so fresh it’s like tasting them for the first time. If available, order the buttery and perfectly pan seared rockfish over fingerling potatoes served with a lemon beurre blanc sauce. It’s absolutely delicious.

Outdoor seating is available on the back patio or charming front porch overlooking downtown. but for dinner with a show, sit at their chef’s counter or a cozy booth in the back in front of the open kitchen. Either way, you’ll be glad you dined here. Reservations are recommended.

The outdoor patio at Foxy's Harbor Grill in St. Michaels, MD

The outdoor patio at Foxy’s Harbor Grille in St. Michaels, MD | Photo: Better Living

Foxy’s Harbor Grille

125 Mulberry St, St Michaels, MD 21663

A 2021 Traveler’s Choice Winner, Foxy’s Harbor Grille, is a fun and casual waterside dining option in St. Michaels overlooking the Miles River. And whether you eat inside, on the deck or at the dockside tiki inspired bar area, every seat here has a water view.

Great for large or small groups, Foxy’s offers an eclectic menu of Maryland favorites like steamed seafood, grilled fish, crab cakes and burgers, as well as a variety of dishes with island flavors.

Foxy's Original Crab Pretzel. A hot, soft pretzel is topped with cheese, scallions, and crabmeat.

Foxy’s Original Crab Pretzel | Photo: Better Living

For some local flavor, try the steamed crab dip topped pretzel or for a lighter bite try their new Kani Salad made with lump crabmeat, jicama, avocado and a tangy cilantro dressing.

Foxy’s is also a great place to head at happy hour to grab a waterside cocktail. Try one of their famous “crushes” or choose from one of their revolving Fifteen drafts on tap.

St. Michaels Nature Trail Covered Bridge

St. Michaels Nature Trail Covered Bridge at Waterfront Park | Photo: Better Living

Getting to St. Michael’s, Maryland

Only 90 minutes from Washington D.C., Baltimore and Wilmington, Delaware and under 2 hours from Philadelphia, St. Michaels on Maryland’s Eastern shore is just off the Ocean Gateway (Route 50).

Those coming by boat can call ahead and have a slip ready at the local marinas or drop anchor in the St. Michaels harbor and catch the Harbor Shuttle water taxi into town. (Call 410-819-9606 or VHF Channel 71)


Arriving by car: St. Michaels has several public lots with free street parking and immaculate public bathrooms.

Arriving by boat: Dock at a local marina and take a short stroll to one of its waterfront or downtown restaurants. 

Places Mentioned

St. Michaels Hotels

The Wildset Hotel
209 N Talbot St, St. Michaels, MD 21663-2103

St. Michaels Dining

Ruse (In the Wildset Hotel)
209 N Talbot St, St Michaels, MD 21663

Bistro St. Michaels
403 S Talbot St, St Michaels, MD 21663

Carpenter Street Saloon 
403 South Talbot Street, St. Michaels, MD 21663

Foxy’s Harbor Grille
125 Mulberry St, St Michaels, MD 21663


Antiques on Talbot
211 N Talbot St # 4, St Michaels, MD 21663

St. Michaels Museums

Chesapeake Bay Maritime Museum
213 N Talbot St, St Michaels, MD 21663

St. Michaels Museum
201 E Chestnut St, St Michaels, MD 21663

Classic Motor Museum 
102 E. Marengo Street St. Michaels MD 21663

Breweries, Wineries and Distilleries

Eastern Shore Brewing
605 S Talbot St, St Michaels, MD 21663

St. Michaels Winery
609 S Talbot St, St Michaels, MD 21663

Bordeleau Winery @ St. Michaels
500 S Talbot St, St Michaels, MD 21663

Lyon Distillery
605 S Talbot St UNIT 6, St Michaels, MD 21663

St. Michaels Coffee, Ice Cream and Gourmet Shops

Skipjack’s St. Michaels
111 S Talbot St, St Michaels, MD 21663

Justine’s Ice Cream Parlor
106 N Talbot St, St Michaels, MD 21663

104 Railroad Ave, St Michaels, MD 21663

Olivins Tasting Room – Aged Infused Fine Olive Oil & Vinegars
110 N Talbot St, St Michaels, MD 21663


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