St. Michaels, Maryland Attractions

The town of St. Michaels, Maryland is a popular destination with a nice mix of history, gift shops, restaurants, lodging, and small town charm.  St. Michaels' combination of popular marinas, inns and bed and breakfasts, shops, and restaurants make it a favorite destination for boaters.  Located on Maryland's Eastern Shore, the town is located near other popular destinations such as Easton and Oxford.  

St. Michaels is known as "the town that fooled the British" due to the clever action of early settlers.  During the early morning hours of August 10th, 1813, British barges off the coast of St. Michaels planned an attack on the town and a harbor fort.  The people of St. Michaels got word of the impending attack and hoisted lanterns high up onto the masts of their sailboats and into the tops of trees.  The high lights caused the attacking British to overshoot the town.  The rouse worked and only one house in St. Michaels was hit by cannon fire.  That house still stands as a private residence and is known as the "Cannonball House."  The cannon ball fell through the top of the roof and rolled down the stairs.  The Cannonball House is located on Mulberry Street, adjacent to St. Mary's Square.

For a good orientation to St. Michaels' history, stop by the St. Mary's Square Museum between Mulberry Street and East Chestnut Street for a St. Michaels Walking Tour brochure.  The tour guides you through the town's historic streets, lined with homes and shops built in the 18th and 19th centuries.  

The Inn at Perry Cabin

Built just after the War of 1812, The Inn at Perry Cabin is a long, pearly white colonial mansion known throughout the generations as the finest hotel on the Eastern Shore. 

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

Take an informative tour of St. Michaels from the water onboard The Patriot.  The Patriot, a 65-foot motorized boat, takes up to 180 guests for cruises along the Miles River.  As Captain David P. Etzel, Jr. narrates, you'll pass historic houses, waterfront estates and native waterfowl. You'll learn all about the history of the land, the people who settled there and the hard-working watermen who harvest Maryland blue crabs, clams and oysters.  Or, enjoy a nature cruise or champagne sunset cruise aboard the Express Royale.  This 50 foot vessel offers cruises of the Miles River from March 15th to December 15th.  The boat departs from the marina at the end of Carpenter Street.

Experience the thrill of sailing aboard on authentic Chesapeake Bay skipjack on the H.M. Krentz or the Rebecca T. Ruark.  Learn about oyster dredging and maritime history on these beautiful old ships.  Contact the captains for sailing times and departure points.

The 41'6" sailing yacht Selina II offers public sails daily from May to October.  The Selina departs for regular 2 hour sails from the dock at the Harbor Inn and Marina.  Click here for more information, schedule and prices.

Be sure to notice the murals of Italian painter Jesse Demolli as you travel around town.  His murals can be found at Character's Cafe, the Rusticana restaurants, the St. Michaels police department, and the scented garden.  Many of his murals feature scenes from St. Michaels' past, inspired by old photographs of the town.  Visit Demolli Art Studio's website for more information.

Visit St. Michaels FreshFarm farmers market every Saturday from May to October from 8:30am to 12:30pm.  Features weekly demonstrations and tastings.  The market in St. Michaels, MD, located in Muskrat Park on the St. Michaels's harbor, at Willow and Green Streets, one block from Talbot Street. 

The St. Michaels Winery crafts boutique wines in the historic Old Mill.  You can visit their tasting room and store, where they sell their wine and other treats such as locally made cheeses, gourmet mustards made with their wine, and premium olive oils and tapenades.  Wine tastings are available daily.  Located at 605 S. Talbot Street. 

Cycling:  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.