At the beginning of September, the Hamptons resounds with the clatter of designer deck chairs going into storage, shutters being hauled down and the collective groan of Manhattan's chattering classes returning to the city. A cavalcade of overstuffed SUVs filters back through bridge and tunnel trailing Kate Spade beach bags and pedigree pooch accoutrements. Such unseemly seasonal migration isn't undertaken by the classiest second-home savants, however. The place to be, especially as fall comes around, is upstate New York.

Like the Hamptons, New York's Catskill Mountains and neighbouring Hudson River Valley are around two hours' drive from Manhattan. And like the Hamptons, this part of upstate New York has an impressive celebrity caché, except luminaries flocking to this region tend to be of the calibre mentioned in the arts section of the New Yorker, rather than caught in indiscreet poses by the National Enquirer. "De Niro, Liv Tyler, Bowie: they're like part of the wildlife," says Kate Pierson, member of the new-wave pop act the B-52s and owner of a new motel near the Catskill's town of Woodstock. "But this area has always been a retreat for musicians and arty urbanites, so celebrities are pretty much left to themselves."

Walk around the nine-acre grounds of Pierson's Lazy Meadow Motel, and it's easy to see why. With the Espopus River and towering Mount Tremper forming a picture-perfect backdrop to this Fifties-style motel, it seems you're not only a world away from modern urban life but an era too. Comprising seven renovated motel rooms, four Airstream Trailers and, to come this summer, two tepees, all fitted out with original mid-century furnishings, Lazy Meadow's clientele comprises Lower East Side hipsters wearing too-small leather jackets and too-big shades. Baby-blue and pink General Electric fitted kitchens grace two of the motel's rooms, flying saucers punctuate the Botticelli sky painted on to the walls of our cabin; our door key comes with a little spaceman key ring.

In the past few years, New Yorkers have been decamping upstate en-masse. Woodstock and its environs are no longer an affordable bolt-hole for boho Big Apple drop outs. Today property prices here are more in line with those in Manhattan. "This area has changed a lot in some ways. It's much more upscale," says Pierson, a resident since 1987. "Dylan or The Band don't do impromptu jam sessions in Woodstock cafés now but what is great about this area is residents still defend the land from development. Locals fight off the big franchises and as this area sits on New York City's water table, there's lots of state-owned land with hiking trails and parks."

The region certainly feels, to an outsider at least, like an America that time (and the Time Warner generation) forgot. The mountain towns, even world-famous Woodstock, are replete with cutesy clapboard houses, and along near-deserted roads, gas stations come franchise-free, often doubling as the local store. The landscape is big, wild (there's bears in them woods) and demands more of travellers than one might expect: snow chains and shovels are winter driving accessories; serious hiking gear for summer treks. "That's why I decided on tepees," says Pierson. "I love camping but like many city people I don't have the gear. Our tepees come pre-pitched and retro-fitted."

Drive around the vast Ashokan reservoir, bordering Lazy Meadow, and you pass state-of-the-art Allaire recording studios, the deluxe wooden ranch that's been home-from-home for Natalie Merchant, Bowie, Moby and countless other local musicians. The studio may have taken the spotlight off Woodstock as the region's recording hub but dinner at the Bear Café, just outside town, reveals that Woodstock's studios still pull in the big names and spawn intimate performances. As we select a confit of locally raised duck from the menu, we note a post-script: Mercury Rev are due to play the little 250-seat Bearsville studio, next door. Film is big in this little town, too. Each October the Woodstock Film Festival, one of the country's best indie cinema events, attracts work by such local resident A-listers as De Niro, Joel Coen and Liam Neeson.

If you're looking for something more "down-home", the region doesn't disappoint: harvest festivals, apple-picking parties and pumpkin cook-offs abound throughout autumn, as do Hallowe'en celebrations, and such Hudson Valley towns as Sleepy Hollow, setting for Washington Irving's eponymous Legend, remain unbeatable for kitsch-me-quick fun.

And then there's the leaf-peeping. A fall driving tour through Rhinebeck and other smart towns lining the right bank of the Hudson is perhaps one of the most gloriously civilised things the East Coast has to offer. This area is littered with the former museum-piece mansions of such old-money names as the Astors, Vanderbilts and Rockefellers. By comparison, Woodstock and other "left bank" towns seem far from gentrified. And with the "love shack" chic of Pierson's Lazy Meadow currently setting the tone, it looks set to stay that way.

The writer travelled as a guest of Virgin Atlantic, which flies several times daily from London to

New York's JFK and Newark airports (; and Carrentals (, which arranges low-cost car hire in more than 4,000 locations worldwide. Lazy Meadow Motel, 5191 Route 28, Mount Tremper, New York 12457, 001 845 688 7200, Double rooms from $169 (£94)