Summer has a way of stealing the spotlight in seaside Newport, which just hosted sailing’s round-the-world Volvo Ocean Race and has long seen its population swell June through August. But fall weather is what New Englanders brag about (ever visit in March?). Clink glasses of Bordeaux under lawn tents during the Newport Mansions Food & Wine Festival (September 20–23) or run waterfront streets during the marathon and half-marathon the city hosts October 7. Recover—from jogging or jugs of wine—at Gurney’s on Goat Island: The hotel spa offers 15 different massages and dry eucalyptus saunas. Alternatively, be ambitious and drive to Point Judith for a ferry to Block Island. Twelve miles off the coast, where street numbers aren’t a thing, you can sit in an Adirondack chair at Spring House Hotel, a sprawling inn high atop a hill, watching boats sail away from the harbor as the island starts to close up shop for the season. Don't worry: You don’t have to leave until tomorrow. —Cassie Shortsleeve