When the air gets crisp and the leaves start to turn, point your bow towards Nantucket. Why visit the Little Grey Lady in the fall? The weather on the island during September and October is on the pleasant side of perfect—and because school’s started and the crowds have gone home, the beach is close to being all yours.

By Jes Ware
The White Elephant

No More High-Tide Prices

Even better, prices have receded summer’s high tide mark. The landmark waterfront hotel, White Elephant, offers a few nights in October for $225 (dates are October 15-17, 22-26, and 29th). For those who prefer the cobblestone streets and cute shops of downtown Nantucket, the White Elephant has two lofts downtown, starting at $1795 during the week and at $1995 on the weekend.

The Wauwinet

Fall's Festivities

Now, if you’re not about to don a bikini and jump into the ocean in October, don’t worry. The White Elephant, and sister properties The Wauwinet and The White Elephant Village, entertain guests who would rather not bask on the beach, with antique car tours of the charming lil’ island and daytrips that let non-islanders try their hand at lobstering. Towards the end of the White Elephant’s season (they close for the winter), mark your calendar for the Cranberry Festival, a good old-fashioned Nantucket way of celebrating autumn: cranberry bog tours, hayrides, fresh local seafood, and Nantucket cranberry harvesting! Just remember to pack a sweater.