Things to Do in St. Michaels, Maryland
The best things to do in St. Michaels, Maryland, are the Chesapeake Bay Maritime Museum, a walking tour of the town that fooled the British and a cruise on the Miles River. St. Michaels is a town of 1,049 people in Talbot County, on a narrow neck of land on Maryland’s Eastern Shore.
On August 10, 1813, a British fleet bombarded St. Michaels for its shipyards and militia battery but did little damage. A story recorded nearly a century later says townspeople dimmed their lights and hung lanterns in the trees so the shots flew high. The nickname was adopted in 1963.
Chesapeake Bay Maritime Museum
This is the main draw. The museum opened in 1965 on Navy Point, where seafood packing houses once stood, and now covers 18 waterfront acres with 35 buildings. It holds the world’s largest collection of Chesapeake Bay boats, the 1879 Hooper Strait screwpile lighthouse and a working boatyard. The floating fleet includes the Edna E. Lockwood, the last sailing log-bottom bugeye and a National Historic Landmark.
★ Good to know On weekends, sign up for the one-hour highlight tour, or take the 45-minute Harbor Highlights cruise when it’s running.
St. Michaels Museum at St. Mary’s Square
This small museum on the town green covers everyday life in 19th-century St. Michaels, Frederick Douglass, and the Chaney House, built by the free Black Chaney brothers in 1851. Douglass spent three of his teenage years in and around St. Michaels, and the town jail held him after an escape attempt in 1835. Guided walking tours leave on Saturday mornings.
★ Good to know Admission is free, and the museum is open seasonally, roughly May through October; the Douglass-themed tour runs the first Saturday of each month.
The Cannonball House
This Federal-style brick house was built around 1810 for shipbuilder William Merchant. It’s known as the house a British cannonball struck during the 1813 bombardment, and it’s listed on the National Register of Historic Places.
★ Good to know The museum’s self-guided walking tour booklet takes you past it; pick one up at the museum or download it.
Cruises on the Miles River
St. Michaels is a boat town, and there are plenty of ways onto the water. The Patriot, a two-deck replica of an old steamer, runs history and wildlife tours in warmer months. You can also sail on the vintage skipjack H.M. Krentz, take a sunset trip on a 44-foot catamaran with St. Michaels Sailing Charters, or ride the St. Michaels Harbor Shuttle.
★ Good to know Kayaks, paddleboards and canoes are available to rent if you’d rather paddle yourself.
Tasting rooms on the harbor
Several makers pour within a few steps of each other. St. Michaels Winery, Eastern Shore Brewing, the Eastern Shore’s oldest brewery, and LYON RUM’s maker, Windon Distilling, all produce on site. Bordeleau Winery also has a tasting room in town.
★ Good to know LYON RUM’s tasting room, the Golden Hour, has cocktails and live music at select times.
Talbot Street
The main street is lined with independent shops, galleries and restaurants, including Book Hounds, a bookstore, and a two-story holiday shop open all year. Blue crabs are the local specialty, and many restaurants look out on the Miles River.
★ Good to know For breakfast, locals send people to the Carpenter Street Saloon for its big pancakes.
Also in town
The Galley does brunch, Justine’s Ice Cream Parlour and Foxy’s Harbor Grille are harbor-side standbys, a Saturday farmers market runs April through November, and Inn at Perry Cabin offers spa treatments, tennis and golf.
Why is St. Michaels called the town that fooled the British?
The story goes that during the British attack of August 10, 1813, residents hung lanterns in the trees so the cannon fire overshot the town. The tale was recorded nearly a century later, and the nickname was chosen for the battle’s 150th anniversary in 1963.
Is St. Michaels walkable?
Yes. The maritime museum, Talbot Street, the tasting rooms and the St. Michaels Museum are all close together, and the museum’s guided tour covers about half a mile in 90 minutes.
What is near St. Michaels, Maryland?
Route 33 continues west to Tilghman Island and east to Easton. A small public ferry at nearby Bellevue crosses the Tred Avon River to Oxford.
What does Frederick Douglass have to do with St. Michaels?
Douglass was born in Talbot County and lived in and around St. Michaels as an enslaved teenager. He came back in 1877 to meet his dying former owner, Thomas Auld. For more Eastern Shore towns, see Easton, Chestertown or our small towns in Maryland.
Where to find them
- Chesapeake Bay Maritime Museum 213 N. Talbot St., St. Michaels, MD 21663 Website Directions
- St. Michaels Museum at St. Mary's Square 201 E. Chestnut St., St. Michaels, MD 21663 Website Directions
- The Cannonball House St. Michaels, MD 21663 Website Directions
- Cruises on the Miles River St. Michaels Harbor, St. Michaels, MD 21663 Website Directions
- Tasting rooms on the harbor St. Michaels, MD 21663 Website Directions
- Talbot Street Talbot St., St. Michaels, MD 21663 Directions
Plan your trip: for events and current visitor info in St. Michaels, see St. Michaels Business Association →
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Where to stay in St. Michaels
Keep exploring
Easton, MDAbout 8 miles as the crow fliesTalbot County's arts town, with a 1684 Quaker meeting house.Things to do in Easton →
Chestertown, MDAbout 31 miles as the crow fliesColonial port on the Chester River, home of the Sultana.Things to do in Chestertown →
Solomons, MDAbout 34 miles as the crow fliesBoating village where the Patuxent meets the Chesapeake Bay.Things to do in Solomons →Also nearby: Havre de Grace · Chesapeake City · Crisfield