How to Spend 24 Hours in St. Michaels, Maryland

St. Michaels Maryland | © Kristina Gaddy for CultureTrip
St. Michaels Maryland | © Kristina Gaddy for CultureTrip
Photo of Kristina Gaddy
9 April 2018

Maryland’s Eastern Shore is home to Ocean City and Atlantic beaches of Maryland and Delaware, but there are also several smaller towns along the Chesapeake Bay worth visiting. Just an hour-and-a-half from both Baltimore and D.C., and right across the Bay Bridge, St. Michaels is perfect for a weekend getaway. Here is how to spend 24 hours in this historic town by the bay.

Grab a gluten-free treat

Bakery, American, $$$
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When you arrive in town, grab a sweet treat at Gluten Free Bakery Girl. This little shop was started by pastry chef Tricia King, and locals love the delicious breads, buns, and cakes that are all gluten-free. You can also get dairy-free and vegan creations.

Rent a bike and take a ride

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Black Walnut Point | © Kristina Gaddy for CultureTrip

Do a half-day or full-day bike rental from TriCycle and explore the area. The roads are very flat and most motorists are used to seeing cyclists. If you want a challenge (and a ride that takes about three hours), pedal all the way down to Black Walnut Point, or just bike around the backroads to enjoy the scenery.

Get lunch at The Crab Claw

Restaurant, Seafood, $$$
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This casual waterfront restaurant is perfect for a seafood lunch. This iconic spot has been open seasonally since 1965, and is a go-to for steamed crabs (if you’re ready to learn to pick the meat out of them) and raw seafood, or safer, non-Marylander options such as crab cakes or fried oysters and shrimp.

Meal service:

Lunch, Dinner, Brunch


Casual, Family Friendly

Check out the Chesapeake Bay Maritime Museum

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Chesapeake Bay Maritime Museum | © Kristina Gaddy for CultureTrip

In the afternoon, be sure to visit the Chesapeake Bay Maritime Museum. Celebrating Maryland’s relationship with the water, the museum has boat-building demonstrations, exhibits on the legacy of watermen and fishermen on the bay, a whole building dedicated to the once-thriving and now-recovering oyster industry, and more.

St. Michaels Winery

Wine Bar, Wine Seller, American, $$$
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The tasting room at the St. Michaels Winery is open year-round, so be sure to stop by to taste some wine made right in town. The winery offers samples starting at 11 a.m. each day, with a variety of whites and reds to choose from. They pride themselves on using Maryland-grown grapes for many varieties of their classic wines, while also having fun, summer wines that are perfect for a picnic.

Eastern Shore Brewing

Bar, American, $$$
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If wine isn’t your thing, or you just want to sample more of what St. Michaels has to offer, check out Eastern Shore Brewing down the street. The beers are brewed on-site, so you know you’re getting the freshest beer in town, and the tasting room offers both pints of beer and sampler flights. The space inside is cozy and the perfect place to relax after a busy day.

Get dinner at St. Michaels Crab and Steak House

Restaurant, Seafood, $$$
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St. Michaels, Maryland | St. Michaels, Maryland

Located in an oyster-shucking shed from the 1830s, this waterfront restaurant gives you a beautiful view of the water and marina with a great menu featuring locally-sourced crabs and seafood.

Stay at a bed and breakfast

There are lots of bed and breakfasts and historic inns to choose from in St. Michaels at a variety of price ranges, plus hotels and motels a little outside of town.

Sail the Chesapeake on a Patriot Cruise

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Before heading home, take a boat cruise on the Chespeake. During the summer months, Patriot Cruises offers narrated historical cruises every day, and Island Music Cocktail Cruises on Saturdays. Tour the water on a replica of a 1930s steamer—the type of boat that crossed the bay to take tourists to bay-side resorts—and learn about the history of the region. The boat has refreshments and air-conditioning.