Best Small-Town Getaways

From mountain haven to coastal paradise, these 17 postcard-perfect towns all make you feel welcome—for a weekend or a lifetime.

St. Michaels, Maryland
Photo: Courtesy Josh Gibson/Orient Express

St. Michaels, Maryland

Once one of the most vibrant ship building and fishing centers on the Chesapeake Bay, today the town about 50 miles southeast of Annapolis contains one of the largest collections of restored 18th-century buildings in Maryland. Elegant and earthy, St. Michaels knows how to party like a gentleman and a sailor—all at the same time.


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