St. Michaels Attractions

St. Michaels Attractions

Things to Do in St Michaels

Chesapeake Bay Maritime Museum and marina
Chesapeake Bay Maritime Museum and marina

It’s probably best to park your car and explore the town on foot.  For a good orientation to St. Michaels’ history and a walking tour map, stop by the St. Mary’s Square Museum between Mulberry Street and East Chestnut Street.  The tour guides you through the town’s historic streets, lined with homes and shops built in the 18th and 19th centuries.

Chesapeake Bay Maritime Museum

St. Michaels’ main attraction is the Chesapeake Bay Maritime Museum. This excellent museum includes an indoor/outdoor collection of items related to Chesapeake Bay commerce & trade, navigation, fisheries, and waterfowling.

Hooper Straight Lighthouse

The museum includes several historic buildings, including the Hooper Straight Lighthouse and a cannery warehouse, plus a collection of 85 vessels.  This collection of sail, power, and row boats is the largest and most important collection of its kind in the world.

The skipjack H.M. Krentz offers daily cruises, departing from the Crab Claw Restaurant. The vintage catboat Selina II has a variety of cruises including sunset champagne cruises and moonlight cruises.   Or, take a narrated cruise on Patriot and learn about the town and local wildlife.  In addition to daily cruises, these boats are available for special events and private charters.

Where to Stay? Find St. Michaels Hotels and Bed & Breakfasts. Make the best choice – all your lodging options, traveler rated and reviewed.

St. Michaels Museum

The St. Michaels Museum at St. Mary’s Square features exhibits about the history of the town and surrounding area.  Visit their website for hours of operation and information on special exhibits and events. St Mary’s Square is bordered by lovely old homes, including The Cannonball House, the only dwelling hit during an 1813 attack on the town by British.

CBMM display
CBMM display

Wineries, Brewery, and Distillery

The St. Michaels Winery crafts boutique wines in the historic Old Mill. Wine tastings are available daily. The winery is  located at 605 S. Talbot Street.

Eastern Shore Brewing is located next door to St. Michaels Winery. The brewery crafts a number of year-around and seasonal brews, which are available for sampling in their tasting room.

Lyon Distilling Company is located just around the corner from Eastern Shore Brewing and St. Michaels Winery, on E Marengo Street.  They a small batch distillery making rum and whiskey. Tastings and tours are available (details).

Great Shoals Cellars offers tasting flights, glasses, and bottle sales of their wines and hard ciders at their Talbot Street tasting room (500 S. Talbot Street). 

Farmers Market

The St. Michaels Fresh Farm Market is open in Saturdays 8:30 a.m. to 11:30 a.m. from April to October.  A “producer only” market at which local farmers sell only what they grow.  Located in the municipal parking lot at 204 S. Talbot Street.


The flat country roads surrounding St. Michaels have wide shoulders and are popular with bicyclists of all ages.  You can peddle a 36 mile circular route from St. Michaels to Oxford (across the Tred Avon River on the Oxford Ferry), to Easton, and back to St. Michaels.  The Easton Business Management Association has mapped out the route on their website.

Shore Pedal and Paddle in St Michaels has bike rentals as well as kayak and stand-up paddleboard rentals.