Best Things to Do in St. Michaels MD This Summer

With wide-open water views, charming historic towns, fresh seafood, and quiet, scenic trails and rural roads that give you plenty of space to breathe, summer on the Eastern Shore of Maryland is nothing short of magical. Towns like Rock Hall and St. Michaels, MD, offer visitors a peaceful coastal vibe with easy access to the best that this region has to offer. From kayaking through the calm waters of the Chesapeake Bay to browsing art galleries or biking along country roads, there’s no shortage of ways to enjoy summer getaways in Maryland.

Despite there being so many things to do in Rock Hall, MD, we also love a good day trip to the charming community of Saint Michaels Maryland. St. Michaels is a vibrant harbor town packed with maritime history, waterfront restaurants, and boutique shopping. It’s often ranked among the best small towns on the East Coast, and it’s easy to see why. Whether you’re visiting the Chesapeake Bay Maritime Museum, sipping cocktails on a waterfront deck, or exploring the local shops and galleries, you’ll find no shortage of things to do in St. Michaels MD.

But when you want to retreat from the crowds and enjoy a truly restful escape on The Bay, there are truly no better places to stay near St. Michaels than our top-rated Rock Hall Bed and Breakfast. We’re a 90-minute drive away, but feel as though we’re in an entirely different (and more tranquil) world. Our Inn is unlike any other, offering spacious accommodations and a peaceful retreat surrounded by nature. With easy access to other Eastern Shore destinations, such as Chestertown, Tilghman Island, and Oxford, this is the ideal home base for exploring the Maryland coast. Book your stay today!

The Best Things to Do in St. Michaels, MD

There’s no shortage of ways to enjoy the laid-back charm of Rock Hall, its unique Waterman culture, and the beauty of the surrounding Chesapeake Bay. But taking a day trip to places like Tilghman Island or St. Michaels, Maryland adds another layer of adventure to your Eastern Shore experience. There are plenty of things to do in St. Michaels, MD, a town offering a mix of coastal beauty and small-town sophistication.

Like many destinations on the Eastern Shore of Maryland, St. Michaels has deep roots that trace back to the 1600s, when it served as a vital shipbuilding hub and later became a major destination for seafood processing and other activities. Today, the town’s charm centers around St. Mary’s Square and its bustling harborfront. You’ll find historic architecture, local art, vibrant festivals, and experiences that celebrate the maritime heritage of Saint Michaels Maryland. If you’re wondering how to make the most of your visit, here’s a curated list of the best things to do in St. Michaels MD:

Take a guided or self-guided walking tour through the historic streets of St. Michaels, starting at St. Mary’s Square.
Enjoy a narrated cruise along the scenic Miles River, perhaps one of the most scenic things to do in St. Michaels, MD.
Sample local vintages at St. Michaels Winery, a relaxed and friendly stop in the heart of town.
Explore the downtown shopping scene, including art galleries, coastal boutiques, and specialty shops. It’s one of our favorite things to do in St. Michaels, Maryland.
Rent a kayak, paddleboard, or bike from Shore Pedal and Paddle and experience the town by land or water.
Spend a few hours at the Chesapeake Bay Maritime Museum, a must-visit destination on the Eastern Shore, where you’ll enjoy a bit of authenticity and plenty of engaging exhibits.
Enjoy a cold craft brew at Eastern Shore Brewing, a favorite way to wind down an afternoon after enjoying many of these things to do in St. Michaels, MD.
Savor the best of the Chesapeake Bay with fresh crab, oysters, and other regional specialties at top-rated St. Michaels MD restaurants.
Stay for the sunset at the harbor, where you’ll enjoy one of the most scenic views on the Maryland coast.

If you have time, consider extending your day trip with a visit to Tilghman Island, just a short drive beyond St. Michaels. This quiet fishing village offers a more rustic and authentic slice of the Eastern Shore, with working watermen’s docks, casual crab shacks, and sweeping waterfront views. It’s a great place to slow down and experience the daily rhythms of coastal life.

The Best Place to Stay Near Saint Michaels, Maryland

While a day spent exploring the harbor town of St. Michaels MD is a must on any Eastern Shore itinerary, nothing compares to coming home to the peaceful charm of the Inn at Huntingfield Creek. Tucked away on seventy acres near Rock Hall, this luxury retreat is consistently ranked among the best places to stay near St. Michaels. It won’t take you long to see (and feel) why. From wide-open skies and waterfront views to elegant accommodations surrounded by nature, the setting of our Rock Hall Bed and Breakfast invites you to truly slow down and relax, in a way you can only do along the famed Chesapeake Bay.

Located within easy reach of Baltimore, Washington D.C., and Philadelphia, Maryland’s Eastern Shore feels like a world apart from the noise and pace of the city. Whether you’re planning a romantic getaway, a coastal road trip, or a few quiet days to recharge, this region of the Maryland coast delivers that just-right balance of comfort, beauty, and connection. Mornings begin with birdsong and homemade breakfast, and your biggest decision comes from whether to bike on the rural roads to places like the Eastern Shore National Wildlife Refuge or spend the afternoon with a great book by the water.

At our Eastern Shore Bed and Breakfast, you’ll find much more than a place to rest your head after a day full of adventure. Every stay includes thoughtful amenities, warm hospitality, and an atmosphere designed to help you fully unwind. Enjoy a chef-prepared breakfast each morning, ideal fuel for a day trip to Saint Michaels Maryland, or any of the nearby towns. When you return, you’ll be reminded that while the towns are charming, it’s this space, which is private, welcoming, and refreshingly still, that makes the Eastern Shore unforgettable. Book your stay at our Bed and Breakfast near St. Michaels, and get ready for an unforgettable summer retreat.