Named for Catherine Pawling, née Beekman, daughter of Henry Beekman, whose patent this once was, this historic town comprises the southeastern quadrant of Dutchess County. The Oblong section was settled by Quakers in 1720; the original meetinghouse still stands. Washington slept here—and more than once; he operated from the John Kane House for two months in 1778. Pawling boasts the Dutcher Golf Course, the oldest public place to hit the links in the United States, but there is money, here, too: the hedge fund manager Paul Tudor Jones, the 369th richest person on earth, lives here, as does talk-show host Sally Jesse Raphael and the venerable actor James Earl Jones. Other notable residents included the preacher Normal Vincent Peale, the publishing magnate William Ziff, and Edward R. Murrow, the broadcasting icon. And if that’s not enough to sell you on Pawling, there’s this: the Trader Joe’s in Danbury is just a hop-skip-and-a-jump away.