The ghost of yuletides past is very much alive during the annual Christmas Stroll. Main Street and much of the rest of the village time travels back to the Victorian era for an old-fashioned winter fest that includes music, crafts, and fair food. Festivities kick off with a Tree Lighting Ceremony and continue with the arrival of Santa and Mrs. Claus via boat at the main wharf.
While you're here: Trek the rolling dunes and while seascapes of the Coskata-Coatue Wildlife Refuge, which wraps around the island's north end.
Where to stay: The waterfront White Elephant has spacious guest rooms in the main building. Rates start at $195; whiteelephanthotel.com.