How to Spend 24 Hours in St. Michaels, Maryland

St. Michaels Maryland
St. Michaels Maryland | © Kristina Gaddy for CultureTrip
Kristina Gaddy

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.

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Grab a gluten-free treat

Bakery, American, $
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.


Black Walnut Point

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.

Check out the Chesapeake Bay Maritime Museum


Chesapeake Bay Maritime Museum

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, $
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, $
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.

Sail the Chesapeake on a Patriot Cruise

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.

landscape with balloons floating in the air


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