MONTAUK POINT OCEAN BEACH
Frankly, I am just so bored with the stunningly beautiful beaches you can lie on extending from Montauk in the east to Westhampton Beach and beyond. Much more interesting to me, anyway, is the ocean beach southwest of the lighthouse at Montauk. It is consistently rated the worst beach in the Hamptons for sunbathing and swimming. Huge boulders impede your way trying to walk the beach. Where there are no boulders, good-sized rocks and pebbles make it impossible to lie down. At the back of the beach is an 80-foot-tall sand cliff, not only impossible to climb but also very dangerous because of its frequent avalanches. Meanwhile, just offshore there are dangerous giant rocks upon which bask harp seals for most of the year. They are cute, but they have sharp teeth and they bite. This beach is not for the timid.

SECOND & THIRD HOUSE
Montauk, way ahead of its time, agreed to name every new building in that town with its own number beginning with one. There were no houses in the town when they decided this. First House was located across from Hither Hills State Park, but it burned down. Second House, built around 1710, still stands and is a museum at the entrance to town on the north side of the Montauk Highway, and Third House still stands and is the ranch house for the Theodore Roosevelt County Park. The entrance is out toward the Point.
The tradition of naming each house has continued to this day. And as houses get built all the time all at different places in Montauk, it has become quite a confusing crazy quilt of numbers. But the Montauk Fire Department has a huge map of all the houses in the town all with their numbers so if someone calls in to say that 814 House is on fire, they know where to go.

THE WALKING DUNES
A series of enormous sand dunes sits to the north of the Montauk Highway accessible by a dead end road known as Napeague Harbor Road. These dunes tower 110 feet up at the top, and are being moved by the winds in a southerly direction toward the Montauk Highway and the ocean. You can see the tops of trees that got swallowed up sticking out of the southern face of these dunes. The Walking Dunes are particularly beautiful at night, when you and your significant other can go up there to sit at the top, look at the stars and encounter the meaning of life, or whatever.

MISS AMELIA’S COTTAGE
This is the absolutely adorable white shingle cottage on the north side of Main Street, Amagansett. It is a perfect example of a colonial saltbox built in the 18th century. Actually it is not an example of it—it is a colonial saltbox built in the 18th century. The house was for years and years occupied by Amelia, and her husband, after she died said he missed her very much. Thus the name, Missing Amelia, which soon got shortened to just Miss Amelia.

LONG WHARF
What is now Long Wharf in Sag Harbor was founded in 1771 at the end of Main Street in that town. It is the proud centerpiece of the community, people walk out onto the end of it and back all the time and you can too. More than 100 whaling ships tied up at Long Wharf in the early 1800s. Occasionally they went out whaling. What we now call Long Wharf was originally called Long Landing. Boats were pulled up to a spit of a beach there, they built a dock and it became Long Dock. When they lengthened it, it became Long Pier and eventually, in the early 1800s, it got its grandest name, Long Wharf, because they had to make it a wharf to get the 100 whaling ships to fit.

EAST HAMPTON TOWN POND
This is a grand body of water where swans glide, ducks paddle and little boys launch model sailboats. It is located at the west end of Main Street in that town. For years and years, it was sometimes a pond but at other times a swamp. In the 1930s, president Franklin D. Roosevelt created a WPA project during the Depression to build a large concrete pipe and culvert at the western end of the swamp so the water could flow freely in and out. The result was the end of the days when the pond was swampy. Feel free to take pictures of FDR’s concrete pipe and culvert.

THREE WINDMILLS
The Main Street of East Hampton is blessed with three old English wood-shingled windmills made in the early 1800s when the English were doing that here. They are the Gardiner Mill, the Home Sweet Home Mill —both along the southern side of the pond— and the Hook Mill at the eastern end of Main Street. The Hook Mill has just undergone a renovation that took two years to complete. For some reason, the giant blades of the mill are made of wood that is thinner than the wood on the other mills, so they are a bit harder to see. I don’t know why they did that. The Hook Mill before the renovation had blades of thicker wood.

SAGG BEACH
Many consider Sagaponack Main Beach to be the most beautiful in the Hamptons. To the west of the beach, Sagg Pond comes within 100 yards of the ocean, but doesn’t link up to let water in or out. Because it is important to let the water in and out for some reason, twice a year, at times randomly chosen by the Town Trustees, heavy equipment—steam shovels, payloaders and trucks—are brought down there to make the “cut” so the ocean and pond connect for a few days to let the water flow out. After that, the cut “heals.” You can watch the “cut” they make when it happens. Just go down to the beach and wait. After a while, the steam shovels, payloaders and trucks will come. It could be a long time, but the wait is worth it. And after that comes the healing.

SCUTTLEHOLE ROAD
One of the most famous roads in the Hamptons is Scuttlehole Road. It runs parallel to Montauk Highway north of Bridgehampton and meanders through farm fields and polo fields near to where Madonna lives. Scuttlehole Road was named after the giant spiders the size of dinner plates who nest at odd intervals in holes along shoulders of this five mile long road. This explains why there are no sidewalks. Drive the length of it, but don’t stop.

GIANT ROCK
A huge boulder, bigger than you can imagine, 15 feet high, stands on the southeast corner of Hampton Road and Flying Point Road. Many tourists take photographs of it. It’s as famous as Plymouth Rock in Massachusetts. You are welcome to go there and look at it, but last month it was stolen.

PROPER ATTIRE
Along the sides of each of the two roads that take you into the heart of Southampton Village are green street signs with white lettering that read PLEASE OBSERVE OUR PROPER DRESS CODES. There is no way to know what the proper dress codes are, because the sign is not big enough to accommodate the code ordinance, but you can guess at it. Or you can go down to Village Hall and have a clerk there read you your rights. Anyway, feel free to photograph these signs. But keep your pants on.

COUNTY ROAD 39
This is the bypass road of downtown Southampton, which has become over time the gateway to the Hamptons. The Dan’s Papers offices are now located on the south side of this road. When it was originally built it was called the Southampton Bypass because that is what it did, but when it got fully developed with all the buildings and everything along the route, “bypass” seemed an inadequate name for it. So it became what it was, which was County Road 39. Two years ago, people in Southampton, tired of the awkwardness and length of that name, voted to give the road another name. They named it after a well-liked local politician who recently passed, so now it is the Edwin M. “Buzz” Schwenk Memorial Highway.

CUSTOMS HOUSE
At the very center of the bridge that crosses the Shinnecock Canal sits the small concrete customs house where you and whoever else is in your car must stop to have your passport stamped by officials as you go from Shinnecock to Hampton Bays or Hampton Bays to Shinnecock. You don’t have to plan to make a stop to visit this place. You will anyway.

From the moment I sat down at the bar in Sag Harbor’s American Hotel, I felt exactly like orphan Oliver Twist in Dickens’ novel when he asks for a little more gruel. Instead of getting hit on the back of my head with a ladle, the bartender offered me a glass of Chardonnay. I would have preferred a whole chilled bottle rather than one glass of wine but with only a hundred bucks left in my bank account until the next paycheck, $10was as much as I could afford. Draining the glass, despite my limited cash flow I felt better immediately.

I was in the Hamptons on the cheap. My wallet was empty but it was OK—I was crashing with a friend who rents the first floor of a house in Sag Harbor. I rode the Long Island Railroad for $14.50 each way , the cheaper but perfectly acceptable mode of transport, instead of taking a helicopter or riding the Jitney, the bus for the elite. Too broke to take a real vacation all summer, here was my chance to get away from it all, if only for the weekend. A mere few hours away from the city, it was the perfect place to lay on the beach by day, tune out at a yoga workshop, and socialize by night. If I had to impose on the largesse of the rich and the powerful, so be it. My friend drives a Jag, her boyfriend owns a 40-foot sailboat, and they both had plenty of leisure time. If I were lucky, they’d take me out for dinner and there’d be some parties to attend, none of which would cost a cent.

Just like in Manhattan, the middle-class—that is, me—can no longer afford the Hamptons, a mecca for celebrities and ostentatious yuppies to show off their expensive toys. Making a big splash into the pools of the Hamptons ain’t easy. If your last name is Hilton, it’s a swan dive but if it’s Grubman, it’ll be a big fat belly flop. “Did I miss Sean “Puffy” Combs’ White Party?” I asked my friend about one of the area’s major power brokers. But it seems P. Diddy’s 8th annual White Party, one of the events of the summer, would be held in St. Tropez this year. What a shame. Loser that I am, I’d already missed the seven previous galas. Nor did I run into residents like Martha Stewart, Alec Baldwin, Billy Joel or Howard Stern.

You can find the Hamptons at its worst with all the trappings of super-materialism and Page Six mentality at its most popular nightclub, the Pink Elephant in Southampton. The place calls itself the “top celebrity and bottle service VIP club in New York catering to socialites, jet setters and Europeans…” Of course, we didn’t get in. The delusional doormen thought the joint was Studio 54, forcing rejects like us to languish at the velvet ropes while “elite” trailer trash like Jessica Simpson, whose bodyguards recently beat up a paparazzo, are welcomed with open arms. “I’m wearing Prada and I still can’t even get in,” a woman at the ropes wailed.

So we switched gears and hung out at the bar in the American Hotel, a yuppie stronghold crammed with WASPs nicknamed Muffy and Biff with rotund dudes wearing Brooks Brothers shirts and suspenders, smoking cigars. Maybe I’d finally meet a real man instead of those guys I’ve been dating from the Internet who want to go all the way an hour after we’ve met. Or who ask to borrow money from me a few weeks later and who, when the bill arrives, tell me they forgot to go to the cash machine.

I knew the lay of the land since back in the early ’90s, my friend and I shared a quaint carriage house in Bridgehampton when rents were low enough for a single girl’s budget. We competed for the cute guys in all the bars that summer, hanging out on employee’s night with the waiters, chefs and sailors who knew how to have fun. We were slumming it up at Murph’s Tavern in Sag Harbor one night when a bipolar carpenter claiming he was a sculptor scribbled his number for me on a damp bar napkin. That’s how I wound up marrying (and divorcing) the only poor man in the Hamptons.

My girlfriend had better sense: one of her trick questions to potential suitors was, “What does your roommate do?” Renters weren’t owners, which meant their bank balances were too low. “If they have to work on Fridays or be back in the office by Monday morning, they’re not successful,” she used to say. And she’d move on to the next one. And here she was now, with a dashing boyfriend who spent the whole damn week with her sailing on his yacht.

The troubles of the world seemed far way in the land of Mercedes and potato fields but if you scratch below the surface, there are lots of people out in the Hamptons who aren’t just sitting around drinking Dom Perignon. For example, this past April a teenage neo-Nazi sympathizer chased three Latino classmates in East Hampton with a machete and a revving chain saw. And police in East Hampton Village expelled day laborers last fall from the train station because of complaints. Lest we forget, Indians were driven off their land on the South Fork by the Puritans years back.

Despite the love-hate relationship, the needs of the rich and the beautiful are met by the service people and laborers in town. The townies, mostly scrappy Irish and Italians, call the summer people “cidiots.” Don’t forget the recent brouhaha over America’s favorite supermodel and longtime Hamptons mainstay Christie Brinkley whose fourth husband, Peter Cooke, was caught fooling around with a Long Island Lolita, a Southampton townie who was a sales clerk in a local toy store. Although Cooke tried to entice his girlfriend with a Nissan Maxima, she left town. That’s what you get when a local tangles with a transplant.

We ended our night at a party held at a tastefully decorated house on Hedgerow Lane thrown by a gay couple. “We sell pretty pictures to rich people,” one of the men confided about their business. Gays flock to the Hamptons since they’ve got the disposable income you need there. A friend of mine—personal assistant to a wealthy gay twosome in Southampton—told me about a hot Latino hustler who serviced men at parties while his dad double-parked out in the front yard, waiting for his son to do his thing. Then there was the party in Southampton with a midget holding a mirror over his head with lines of cocaine, ready to be snorted by the guests. We didn’t notice anything amusing like that, but the drinks were served by “eye candy,” breathtakingly hunky, bare-chested waiters and poolboys chosen for their ability to look pretty wearing tight white cargo pants toting trays with their biceps bulging and chests rippling. The eye candy was the most popular dish of the night. Looking was free and we wanted to sample the sweets, but it was getting late. In the end, everyone who’s anyone knows the Hamptons has become a cliche except maybe the high tax bracket yupsters who continue to summer there, no matter how high the real estate becomes. As Yogi Berra would’ve said, “Nobody goes anymore. It’s too crowded.” n