Named the "quintessential New England village," the town of Woodstock is chock full of charming Americana, including a covered bridge smack in the center of town and a village green surrounded by restored Georgian, Federal Style and Greek Revival homes. Spend a day wandering under the shade of 400-year-old hemlock trees at the Marsh-Billings-Rockefeller National Historical Park and then revitalize yourself at Sugarbush Farm, where you can taste maple syrup or 14 varieties of cheese for free.

The legendary Hamptons, a cluster of wealthy enclaves on Long Island's South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.