Out of Here

It’s hip to be there

Whether you’re a Gen Y baby hankering for the liberal past you never had or an aging yuppie yearning for your glory days, UPSTATE NEW YORK is perfect nostalgic wallowing. Woodstock—(home of those untidy music festivals) caters to all your new-age hippie needs at its quaint boutiques [woodstockchamber.com]. Saugerties offers lush country vistas, fine antiquing, arts festivals, auto shows, and upscale equestrian events. You’ll need wheels, as public transportation is nonexistent. Kip at a cozy B&B in either town, or opt for the kitschy glamour of Kate’s Lazy Meadow—a renovated motel in nearby Mt. Temper owned by Kate Pierson, chanteuse for the B-52’s [lazymeadow.com]. And don’t forget the smashing Dutchess County Fair. —Leigh Jerman

illustrated postcards: Tim Silbaugh

The end is near

Unlike the Hamptons—its glitzy neighbor to the west—MONTAUK [montaukchamber.com] doesn’t put on airs. This laid-back land’s-end community on the easternmost tip of Long Island is surrounded by water on three sides and characterized by serene, rolling hills and steep sand bluffs. Most New Yorkers who make the three-hour drive to vacation here think of it as their secret destination. They even walk around proudly in T-shirts or sweatshirts emblazoned with the words “The End” or “Montauk.” After a day of lazing around on Hither Hills’ gleaming white beach, eating the world-class lobster rolls at Duryea’s Lobster Deck, you’ll be sporting the official town attire too. It’s inevitable. —Grace Bastidas

Philly stakes

Just over two hours away by car or train, PHILADELPHIA [gophila.com], offers more than just colonial monuments: Visit the Mütter Museum; see Dalís galore at the Museum of Art (through May 15th) and explore architectural marvels like Frank Furness’s gorgeous Academy of Fine Arts in Philly’s eclectic downtown; bargain for CDs at AKA Music, then get all collegiate at the funky shops along South Street after you gobble down a Jim’s “Whiz” cheesesteak. And for upscale dining, Philly one-ups Manhattan with Buddakan and the very swank Morimoto (the Iron Chef’s eponymous restaurant). —Lawrence Ferber