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Historic Homes & Buildings

  • Cannonball House
    During the Battle of St. Michaels in the War of 1812, a cannonball penetrated the roof of this house, where lovely herringbone chair rails, pine mantels, and a curved arch in the lower hall remain original. This was the only house struck, thus it's name. The story tells of residents tricking the British into overshooting the town by calling a mandatory 'blackout' then hanging lanterns in the trees or on masts of ships.

Museums & Galleries

  • Chesapeake Bay Maritime Museum
    Mill Street, P.O. Box 636 • St. Michaels, MD 21663
    410-745-2916
    Encompassing nine exhibit buildings, this maritime museum is designed to educate and preserve the cultural and maritime heritage of the Chesapeake Bay region through exhibits as well as special programs, events and workshops. The museum includes a lighthouse and the world's largest collection of traditional bay boats. more...

  • Museum of Costume
    400 St. Mary's Square • St. Michaels, MD 21663
    410-745-5154
    Housed in a home, built in 1843 by Sea Captain Lewis Tarr, this museum exhibits historical fashions and features a childrens room and other exhibits reflecting early lifestyles. Open daily, April-November, 11am-5pm.

  • St. Mary's Square Museum
    P.O.Box 714 • St. Michaels, MD 21663
    Saint Mary's Square
    410-745-9561
    The Square was a feature of the original plan for the town of St. Michaels, and currently two circa 1860 buildings, display artifacts and memorabilia from the early days. The "Mechanics Bell" which measured the working day for carpenters in the nearby shipyard is housed here and is rung every day. Walking tours are available anytime with 48 hours' notice.  more...

Tours & Cruises

  • Selina II Charters
    101 North Harbor Road • St. Michaels, MD 21663
    Located at St. Michaels Harbour Inn & Marina
    410-726-9400
    A 40', 1926 Historic Catboat offering two-hour sails daily. Arrange for a two-hour, 1/2 day, full day, champagne sunset sails, private charters, overnight excursions, birthdays, anniversarys, engagements and weddings. Limiting guests to just six passengers, Selina II offers you an intimate taste of the history of sail.  more...  map

  • "Let It Ride" Charter Service
    308 Watkins Lane • St. Michaels, MD 21663
    410-745-2200
    Offering scenic tours, special events, sunset cruises and fishing on the Bay, Let It Ride caters to both corporate or private parties. more...

  • Dockside Express Tour and Shuttle Service
    P.O. Box 803 • St. Michaels, MD 21663
    St. Michaels Harbor
    410-886-2643, 888-31-CRUISE
    By land or water, Dockside Express provides transporation around or to and from the town of St. Michaels and offers narrated harbor tours, sunset boat cruises and charters, and moonlight cruises. more...

  • Patriot Cruises, Inc.
    Mill Street, P.O.Box 1206 • St. Michaels, MD 21663
    410-745-3100
    Historic, narrated cruise of Miles River tells the history of Talbot county, passes waterfront estates, regional waterfowl, and hardworking watermen as they harvest the abundance of seafood in the area. This 180-passenger vessel departs daily and is available from April through November. more...

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