Spending A Day in St. Michaels
St. Michaels is one of Maryland’s favorite small towns—complete with Chesapeake charm, waterfront views, amazing restaurants, and relaxing resorts. A day trip or weekend could include several gourmet meals, happy hour on island time, a crab feast, learning all about the Chesapeake Bay, and a relaxing stay in a spa and resort. If the kids are along, there are plenty of boating opportunities and delicious ice cream. Here are a few of our favorite spots.
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Chesapeake Bay Maritime Museum Learn about life on the Chesapeake Bay—its history, oysters and crabs, boats, and lighthouses—at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland biggest maritime museum on the Bay.
Corah’s Corner has a great, local music scene-all summer long!
Patriot Cruises
Hop on board for narrated cruises of St. Michaels Harbor and the Miles River.
Bike St. Michaels – Easton, Oxford, and St Michaels are beautiful old bayside towns with interesting architecture, food, and shops. My favorite way to experience the area is by bicycle. The St Michaels-Easton-Oxford loop is an Eastern Shore classic bike ride. Whether biking or driving, take the Oxford-Belleview ferry across the Tred Avon River.
Stay in St. Michaels
Come by land or water and get pampered at these Bayside resorts, where luxurious accommodations allow you to slow down and relax in style.
Inn at Perry Cabin Originally a farm, the Inn at Perry Cabin is a luxury resort designed for visitor comfort and enjoyment. Bikes, boats, a spa, golf course, and a zero-edge swimming pool are some amenities.
St. Michaels Harbour Inn, Marina and Spa. Sail or drive in, enjoy the spa and pool at the inn, or take advantage of bikes and a car service to take you into St. Michaels to explore.
Eat in St. Michaels
Ava’s Pizzeria Handmade and brick-oven fired gourmet pizzas, extensive wine bar, great beer on tap, plus patio dining!
Crab Claw. This classic Bay crab house is just what you want when you think ‘crab feast!’
Foxy’s Harbor Grille. Feel like you’re on an island with a cold drink in hand and a steel-drum band playing at Foxy’s!
208 Talbot. An upscale dining experience you don’t want to miss.
Stop at Skipjack’s St. Michaels for a coffee and Smith Island cake! They have decadent desserts.
Drink
Eastern Shore Brewery The oldest brewery on the Eastern Shore of Maryland, this brewery serves award-winning beers and has an eclectically decorated meeting place.
St. Michaels Winery Come taste one of the 18 wines in their cellar. Open daily until 5 pm, 6pm on Friday and Saturday.
Lyon Rum and Distillery Their signature line of rums paying tribute to the rich, spirited traditions of the Eastern Shore. The spirits shop is open daily for sales & sampling of their signature spirits.
Shop in St. Michaels
All along Talbot Street, you’ll find everything from boutiques and art galleries to gift shops and ice cream parlors. It’s the perfect small-town Main Street with updated shops, restaurants, and fun.
J.K. from Silver Spring suggests, “Walk one side of Main Street to the end, make a legal u-turn (too much gps in my blood) and walk the other side. Lots of good shops. A very good ice cream store, a great dinner place in Limoncellos, and an amazing pizza lunch place called Ava’s. Boat tours are are available. There is an interesting cemetery in town near the year-round Christmas store. We always go to the winery–in town at the end of the shops, and sample a few. Buy a glass of wine and sit in their outside patio. Great Maritime Museum as well.”
