A Field Guide to the Hamptons

Let's get one thing out of the way immediately, because it will inform everything you know about the Hamptons, the collection of beach towns at the eastern tip of Long Island, New York. The first rule of the Hamptons is never leave your Hampton. The territory in question might be tiny, some 30-odd miles; but we're talking about the playground of privileged New York City, and New Yorkers know how to pack a lot into small spaces.

The differences among the villages are slim, which is why they're collectively known singly as the“Hamptons.” Since the 1600s the area has enjoyed a long and noble history of bitchiness and scandal, but let's talk about now, people. This is where New Yorkers – Manhattanites in particular –come to see each other's bare legs, to drink bottomless bottles of rose on the beach, to get laid foolishly and cram in an awful lot of yoga in between.

Navigation
The tragedy of the Hamptons is that unless you've called shotgun in your hedge fund pal's chopper, you'll join the rest of the hordes jammed on the same damn road, Route 27, which is also called Montauk Highway, though there's nothing speedy about it. The Long Island Railroad will transport you from Manhattan, as will the Jitney and Luxury Liner buses, but for getting around, it's Route 27 and you're stuck. A road sign claims it's the “coastal evacuation route,” but if disaster strikes, you're screwed. There's nothing secret about the back road shortcuts, either. They're just as congested with the smug drivers. Traffic: Yet another reason never to leave your Hampton. Ever.

Don't Call This a Hampton
The Hamptons begin in Southampton and not, as you might think if you applied a shred of logic when looking at a map, in Westhampton. First, let's quickly dispense with the towns to skirt around:

Westhampton doesn't count. It's full of tacky, overcrowded share houses brimming with twentysomething advertising account managers who can't hold their vodka Red Bulls.

Quogue might count, though it prides itself on quietly and modestly existing above the chattering fray. Ironically, this is where Tina Brown, the queen of the scene, has pitched up. Apparently, even she needs respite from the hand that feeds.

Hampton Bays is the point before Route 27 narrows from four lanes down to two and the drive from Manhattan comes to a crashing halt. People stay in houses here, but you don't want to know them.

Find Your Hampton
Safely out the other side of Hampton Bays, you're beyond the fray. The Hamptons begin here. Pay attention now, finding the Hampton that fits you best is important and the stakes are high. Don't make me restate rule one, never leave your Hampton.

Southampton is the haven of old money, who retreat to their grand, well-staffed mansions to age gracelessly. Not that you'll ever get to see them: An oceanside drive along Gin Lane up to Wickapogue Road won't reveal much more than a long barricade of hedgerows, groomed over decades to block the view from unwanted, wandering eyes. You'll be hard-pressed to see the street numbers in front of these stately piles. If you don't know where you're going, you don't belong. There, there, head back to town and console yourself with an overpriced gelato at St. Ambroeus.

Bridgehampton is the haven for artists and writers. It's at the psychological midpoint of the Hamptons, straddling the conservative wealth to the west and the look-at-me ego to the east. It's accessible, it's friendly, its shops are still primarily mom-and-pop operations. It's also home to KMart and King Kullen supermarket, the cheap mega shops where everyone supposedly hates to shop. It's awesome.

Sagaponack is the hamlet of Bridgehampton known for exclusivity, wealth, and, most unexpectedly, farming. Sagaponack abounds in overdeveloped glitz: The ambitious Houses at Sagaponac project includes designs from architecture's best, while Ira Rennert's monstrous Italianate estate, the largest single family home in the United States, is out of sync with the Hamptons housing aesthetic, which can best be describes as “weathered shingle.” Yet the area remains surprisingly farmy. The parking lot at tony Gibson Beach abuts a potato field, the Wolfer Estate is one of many nearby vineyards, and Pike's Farm Stand rates second only to Foster Farm, where owner Marilee Foster illustrates vegetables with charming little drawings and shoppers puts money in the till according to the honor system.

Sagaponack is also where everyone shows up on Sunday night for the movies that one local shows on his front lawn. You bring your folding chair; he provides the popcorn. One movie you're unlikely to catch here is A Widow for a Year, which John Irving set on Parsons Lane, a few blocks away.

Sag Harbor, at the north end of Sagg Main Road, an old Native American path, is the anti-Hampton. It's a proper village on the bay, with no real beach, the charming American Hotel, an indie movie theater, THE power-scene yoga studio, and restaurants that stick around for more than one season. Southampton and East Hampton may also have these, but Sag Harbor is the only town with the feel of full-time residency.

Wainscott is Sagaponack-lite, except for the Georgic Association, a private compound of mock tudor-homes on Georgica Pond that's so exclusive you need to be approved by a watch guard. He won't approve you.

East Hampton! Yeah! This town LOVES to look at itself! Over here, Martha Stewart. Over there, Steven Spielberg. Oh, Bill Clinton's back. This is where media and fashion titans come to show off their beachfront, to pretend to care about the nesting rights of the piping plover birds, and to jockey for a table at Nick and Toni's restaurant by night and shop at Ralph Lauren, Hermes, Tommy Hilfiger, Tiffany, and Tory Burch by day. And where their hormonal offspring misbehave.

Amagansett is for those who like their Hamptons a little quieter but can't commit to driving as far as Montauk. Yes, it has its players – every Hampton does – but the scene is more subdued, slightly more modest, and its renters strive to keep it like that as they hide out in their homes amid the dunes.

Montauk is as far east as you can go without falling into the sea. It's a narrow strip filled with ponds and surrounded by ocean and lots of glorious waves. This is where New Yorkers come to pretend they're Hawaiians, surfing and smoking pot and living the materialistic version of the hippie lifestyle. They're proud in Montauk. And what's more, they're cooler than you are.

In the interest of full disclosure, this author's Hampton is Sagaponack. Why do you think it's described so much more lovingly than the others? Come on: It's my Hampton. You think I'm going to like yours nearly as much?

This story was originally appeared on Beach Tomato and is reprinted with permission.