How To Spend 24 Hours In St. Michaels Maryland

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.

As well as a perfectly curated itinerary from our local expert, we’ve also picked out a selection of experiences you’ll want to take to make the most of your day in Maryland.

Grab a gluten free treat

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.

If you want to sample more local cuisine, this walking food tour is the perfect treat.

Rent a bike and take a ride

Do a half-day or full-day bike rental from TriCycle and Run 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.

Why not take a historical tour of Baltimore while you’re here?

Check out the 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.

Enjoy an inner harbour sailing experience suitable for novices for a real taste of the maritime life.

Autumn colours in Chesapeake and St Michaels

St. Michael’s Winery

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

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.

If you have 75 minutes to spare in Maryland and still want to hit the water, we recommend this parasailing adventure above Ocean City.