St. Michaels and the Chesapeake Bay, Maryland.

This Small Chesapeake Bay Town Has The Best Downtown

While the Chesapeake Bay is often praised for its beaches, wetlands, and wildlife, locals know that some of the most memorable experiences happen right within city limits. And if any place deserves recognition for its remarkable downtown district, it is St. Michaels, Maryland. Despite having only about 1,000 residents, this small town on the Miles River is bursting with attractions, most of which are easy to reach on foot. The lineup includes maritime museums, coffee shops, farmers' markets, and waterfront inns, all close enough that the car can stay parked the entire weekend. So get ready to hit the streets of St. Michaels and find out what makes its downtown so memorable!

Culinary Scene

Shops and stores along the main street of St. Michaels, Maryland. Image credit George Sheldon via Shutterstock
Shops and stores along the main street of St. Michaels, Maryland. Image credit George Sheldon via Shutterstock

St. Michaels’ culinary scene is fantastic for a town of its size, with many dining establishments concentrated on or near Talbot Street. Visitors who arrive in town in the morning can start their day at Blue Heron Coffee, a local coffee shop on Talbot that serves coffee sourced from sustainable, family-owned farms. You’ll find all kinds of beverages on the menu, including drip, pour over, French press, cold brew, chai lattes, iced tea, and much more. Later on in the day, when lunch rolls around, head over to Foxy’s Harbor Grille, a waterfront bar and grill that is known for its seafood, crabcakes, burgers, and rotating craft beer selection.

All that strolling during the day is bound to work up a mid-afternoon appetite. If a sweet tooth strikes, make a quick stop at Justine’s. This ice cream parlour has been a town favorite since its opening in 1987. In addition to the classic flavors, you’ll find unique seasonal varieties like pumpkin, eggnog, and butter pecan! To finish off the evening, consider making reservations at Bistro St. Michaels, a farm-to-table restaurant that creates chef-curated menus using seasonal ingredients. A few of the dishes you can currently find on the menu include braised beef short rib, roasted duck breast, and wild mushroom risotto.

The Chesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Photo credit JE Dean via Shutterstock
The Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Photo credit JE Dean via Shutterstock

The Chesapeake Bay is, of course, filled with maritime history, and St. Michaels is fortunate to host one of its best-preserved examples: the Chesapeake Bay Maritime Museum. This museum sits right in the heart of town on the coast and has all kinds of outdoor and indoor exhibits to see. A few of the attractions you can find here include a floating fleet of historic vessels, a working shipyard, and a historic lighthouse.

You can also sign up for a boat cruise with the CBMM. On a Patriot Cruise, for example, passengers can enjoy an excursion on the Miles River aboard a 65-foot, 149-passenger vessel that resembles a historic Chesapeake Bay steamboat. During cruising season, rides can consist of either a 70-minute historical narrated cruise or a 90-minute happy hour cruise.

Shops, Markets, and Galleries

Talbot Street in St. Michaels, Maryland. (Editorial credit: Albert Pego / Shutterstock.com)
Talbot Street in St. Michaels, Maryland. (Editorial credit: Albert Pego / Shutterstock.com)

If you’re the kind of traveler who can’t leave town without a souvenir, rest assured that St. Michael’s has you covered. Talbot Street has numerous boutiques and gift shops, starting with Chesapeake Trading Co., a book and apparel store that has been in the community since 1992. The Preppy Redneck is just about a block down the street, selling gifts, jewelry, home decor, clothing, and pet supplies. This one is pet-friendly, so feel free to bring your dog in with you!

For some art, stop by Studio 2 Saint Michaels, a beloved gallery in town that showcases work from local artists in a wide range of media, open on Saturdays or by appointment. From April through November, travelers can also stop by the St. Michaels Farmers Market on Saturday mornings. As a producer-only market, everything you find here is local, completely supporting the local community and farmers.

Local Inns

Part of St. Michaels Harbor in historic Saint Michaels, Maryland.
Part of St. Michaels Harbor in historic Saint Michaels, Maryland.

St. Michaels’ cozy inns are the perfect way to round out a weekend downtown. Travelers hoping to stay on the water will love the St. Michaels Harbour Inn, Marina & Spa, a year-round, luxurious inn that sits right on the harbor. This hotel has a wide range of amenities, including a boat slip rental, a waterfront restaurant and bar, and a spa that provides massages, facials, and body treatments. Each room offers its own set of amenities as well, ranging from marina and river views to fireplaces and spa tubs.

If you prefer a more historic stay, look no further than the Parsonage Inn, a historic bed and breakfast that is housed in a home that dates back to 1883. Celebrated for its elaborate architecture, this inn stands out with its extensive brick detailing and paneled brick chimneys. To top it all off, you can enjoy a full hot breakfast here each morning, beginning with a starter and concluding with a delicious main course.

An Abundance Of Attractions

Boats docked in the harbor in St. Michaels, Maryland.
Boats docked in the harbor in St. Michaels, Maryland.

The attractions above are just the beginning of what you can discover in this Chesapeake Bay town. In addition to the attractions already mentioned, you can also find waterfront parks, a motor museum, and even a winery right in the heart of St. Michaels. As a result, you can rest assured that you will stay busy all weekend long, enjoying an itinerary tailored to your own interests. Who knows what else you might discover during your visit?

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