On the Eastern Shore 40 mi/65 km southeast of Baltimore, St. Michaels, Maryland, is a picturesque town that was once a shipbuilding center and is now popular with travelers; it merits a daylong visit.
St. Michaels' inhabitants are perhaps most famous for having fooled the British during the War of 1812: They hung lanterns in trees outside the town, causing a British nighttime bombardment to miss the mark entirely.
St. Michaels can be crowded, especially in summer. Tourists converge on the town from both land and water, and lots of pleasure boats call at the harbor.
The area's ties to the sea are the focus of the Chesapeake Bay Maritime Museum. It contains lots of memorabilia and the 1879 Hooper Strait Lighthouse, as well as a working boatbuilding shop. https://cbmm.org.
Also, the annual St. Michaels WineFest is held in October. https://www.winefestatstmichaels.com.
The other big attraction is the town itself. Spend some time strolling the crooked streets to see the old buildings.
Nearby Tilghman Island is connected to the mainland by a drawbridge. The island is a good place to eat seafood and watch the activity of the watermen who make their living by harvesting crabs, oysters and fish from the bay. The work boats, particularly the white-sailed skipjacks, are picturesque and fascinating. You can make arrangements to accompany the watermen on a crab boat or skipjack.
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