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Hillbillies in the Hamptons


The Hamptons.

Beautiful people living in beautiful houses on beautiful beaches.

My minimal (and largely inaccurate) knowledge of the Hamptons came primarily from TV shows and movies that take place in NYC. You know the ones where they say, “Let’s go to the Hamptons for the weekend.” All I knew was that it was expensive, everyone was supposed to wear white everywhere, and you needed an expensive car and a well groomed standard poodle to gain admittance. It was not a place I ever intended to visit.

Not because it’s not nice. It’s obviously nice, but it’s just too far from us to be practical. Besides, Matt doesn’t own any plaid shorts or pink polos.

I had always been scared off by visions of mega-mansions and pretentious nightclubs and Lilly Pulitzer prints.

Imagine my surprise when I found myself planning a trip to the Hamptons due to a weekend charter Matt had booked.

Given that most accommodations in the Hamptons rent by the summer, not the night, my first inkling that we were seriously out of our league was when I tried to find a hotel or inn. Apparently, there are only 2 categories of accommodations in the Hamptons that rent by the night, particularly when you only have a weeks notice: a “retro chic, cozy room” for about $400 a night (aka, small, dingy motel room) or what would be considered a decent room for $700 a night and up.

I started to wonder if I could get a futon mattress in the back of the plane.

I had a stroke of brilliant luck and found a cute cottage that was a summer rental, but the summer person wasn’t taking it until July 1. The owner let us have it for an amazing price. So much better than pitching a tent at the airport and setting up a Hibachi to make grilled cheese for dinner.






Now I just needed to find some white pants, oversized sunglasses, and a dog that could fit inside my wallet.



We left Tennessee on a steamy, hot, humid June morning. Temperatures were already soaring, so I was looking forward to heading north. I could feel the temperatures dropping and could see the landscape change below me as we flew to Long Island.

I knew we had reached our destination when I saw a gorgeous coastline, rolling green forests, and a 24,000 square foot house on every lot.





We landed in Westhampton and dropped off our passenger and proceeded on to East Hampton airport for two reasons: 1) It was closer to the things we wanted to see and 2) It didn’t charge a $130/night tie down fee like Westhampton.

When you pay more to park overnight than you are used to paying for a hotel room, you know you are in trouble.

So. Here we were. We were in the Hamptons.


A collection of beach towns on the eastern tip of Long Island, NY, “The Hamptons” are made up of several villages, each with its own unique personality and vibe. The area has a long and noble history and is where Manhattanites escape for weekends in the summer to drink bottles of rose on the beach, eat several outrageously expensive meals, show off the expensive sports cars that they can’t drive in the city, and cram in a lot of Pilates and Spin Classes in between shopping for Tory Burch tunics and drinking afternoon espresso.

Because there were several areas to choose from and I only had a week to prepare, I quickly sent a frenzied email to Hamptons wiz TraceyG, whose blog, Escape From New York, is replete with Hamptons information. She quickly gave me the lowdown.

Apparently, the Hamptons begin in Southampton and not, as might seem indicated by the name or any amount of sense applied while looking at a map, in Westhampton. Westhampton, Quogue, and Hampton Bays, while nice, are not REALLY the Hamptons. In a local survey, Hamptonites voted overwhelmingly that “The Hamptons” begin at the Shinnecock Canal, and since poor Westhampton is on the wrong side of the tracks the canal, Westhampton = Wronghampton. Simpler and less pretentious, these areas are still striking and upscale, but we were in the Hamptons to be wowed and amazed, so we had to go a bit farther.

Not so far as Amagansett or Montauk, however. Apparently, that was too far. The Hamptons appeared to be very much like Goldilocks and her porridge…you had to get it just right. If Westhampton is Wronghampton, then Amagansett and Montauk are Anti-Hampton. Far on the opposite end of the Hamptons continuum from Westhampton, Amagansett and Montauk are the quieter, more laid back side of the Hamptons. It’s where New Yorkers come to smoke pot, wear fedoras, eat clams, and pretend they are bohemian surfers. It’s more Havianas and hoodies than Gucci and Givenchy.

“Just Right” in our Hamptons fairy tale seemed to be the cluster of small, close villages in the center – on the “right” side of the canal but not so far that we’d fall off into the sea. We were going to stick to Southampton, Bridgehampton, Sagaponack, Water Mill, East Hampton, and Sag Harbor.

Our impression was immediate. The Hamptons were not subtle. They were extreme. There was an abundance of overpriced real estate, a mansion on every corner, and more Bentleys than you could shake a stick at. It was expensive. It was pretentious. It was showy.

It was beautiful.







There is a reason so many people flock to the Hamptons on every sunny weekend in the summer. And it’s not because they are hoping to catch a glimpse of P. Diddy in plaid golf pants.

There was something about this place with its sprawling wide beaches and dramatic dunes, it’s quaint pedestrian villages filled with bright awnings and flowerboxes, and that famous “special light” that has been attracting artists and vacationers for decades.

I figured out that the Hamptons don’t have to be about celebrity pool parties, extravagant boutiques, and stilettos with designer bags. I realized quickly that it can be about outdoor cafes, beachcombing, rose colored sunsets in the grass with a glass of wine, antique shops, homemade cookies, and farmer’s markets. Sure, you might trip over Richard Gere over as your run out of the coffee shop with your morning cup or you might realize that cute kid on the beach is holding J Lo’s hand, but the Hamptons can be enjoyed on whatever scale you decide is right for you.

Unfortunately, our scale started off with a $168 lunch.

Matt quickly told me to adjust the scale.

We realized quickly that, as expected, everything in the Hamptons is really expensive. Really. Expensive. Like, if it is $3 at home, it is at least $1000 in the Hamptons. A cup of coffee is $1000. A gallon of gas is $1000. An ice cream cone is $1000. And that price has probably gone up since you started reading this.

We only had 36 hours and the clock was ticking, so we had headed straight for Southampton for lunch.


A haven of old money, Southampton is where the old rich retreat to live out their golden years in opulent luxury.

Not that you will ever see them.

Our Oceanside drive along Gin Lane to Wickapogue Road revealed no more to us than the fact that one could get rich in the Hamptons selling privet hedge. Damn their mile high privacy shrubs, obviously designed to keep out the wandering eyes of riff-raff like us.




As we drove past one estate after another, we came to an immediate realization of just how poor we were and decided to console ourselves with an expensive lunch.

We found ourselves at Tutto il Giorno, a beautiful restaurant designed by the daughter of Donna Karan. Seated on the sunny patio, surrounded by ladies who lunch and lush foliage, we felt compelled to do it up right. When in the Hamptons…..right?




Sure, a bowl of spaghetti with tomatoes and basil was nearly $30….but somehow, it was so worth it. The food was delicious, the setting screamed “YOU ARE IN THE HAMPTONS!,” and it appropriately started the trip off with a lavish bang.






Next up was some Southampton window shopping. I say “window shopping” because we couldn’t actually afford to buy anything. We should have been clued in when the cheapest car in the parking lot was a BMW. Apparently, the BMW and Mercedes are the Hyundai and Kia of Long Island. We counted 5 Ferraris in less than an hour.

It was like being at a car show.




The shops were lovely, though. It was a great place to wander and look at things I never knew I needed but suddenly had to have, because, well….they were in the Hamptons so they must be fabulous.








“Matt….look….this tiny salt bowl is only $48. I need it. WE need it.”

That’s when he used a foolproof method of keeping me from buying anything. He distracted me with cookies.

Tate’s Bake Shop in Southampton sells world famous cookies. There was a dizzying array of sweets and pastries. I saw everything from buttery croissants to artisan breads to brownies and muffins. There was a large circular table filled with their famous chocolate chip cookies in all varieties.



I however, opted for this fresh baked monster. I have no idea what was in it. But I immediately forgot all about that $48 salt bowl.


Matt’s peanut butter filled cupcake wasn’t too bad either.


We headed back to our cottage to freshen up before heading to Bridgehampton for the evening. We were tired, but with only 36 hours, we had an ambitious schedule. I did not fly all the way to the Hamptons to sit in a one room cottage and watch Matt watching old Rambo movies in his underwear.

Bridgehampton was smaller and quainter than Southampton. It seemed more artsy and eclectic, accessible and friendly. It was filled with Mom and Pop type shops and I didn’t see one Ferrari.

It had a K-Mart.

I immediately felt more comfortable.






We stopped in at the Candy Kitchen to sample some of their home made ice-cream. It looked like something straight from my childhood.

Despite a hankering for coffee ice cream, I let the pre-pubescent girls working the counter talk me into mint chocolate chip, which they claimed was the best. I have to give them credit, it was good.



Then it was time for more shopping. I lingered over a cool pair of swim trunks for Matt before realizing they were $248. And a dress for me that was $698.

I started thinking about going back to that K-Mart.

With only 36 hours in the Hamptons, and wanting to sample as many dining options as possible, we found ourselves becoming Hobbits. It was time for second lunch. Or was it first dinner?

Whatever it was, we headed to Almond in Bridgehampton to do it.




The beautiful restaurant was completely deserted at the early hour, since it is more common in the Hamptons to starve for three hours after you are actually hungry for dinner so that you can eat fashionably late. Eating early is an obvious faux pas. It’s as bad as passing gas in an elevator.

Or going to the Hamptons K-Mart.

Since we had late night reservations at one of Southampton’s uber-hip dining spots, we allowed ourselves to indulge our early bird tendencies at Almond without it making us feel like a membership to AARP was the next logical step.

We chose to sit outside, despite the early evening chill that was upon us. I was in the Hamptons, darn it, and I was going to sit outside and watch the beautiful people go by as I sipped a cocktail, even if it meant my teeth were going to chatter while I did it.


Unlike the rest of the United States, summer doesn’t actually start in June in the Hamptons. I think it starts in August and lasts about 2 weeks.

My resolve NOT to bundle up in jeans and an old lady sweater was being severely tested.

To distract me from the fact that it was a tad chilly and I insisted on wearing my sleeveless maxi dress, I made up a drinking game.


It went as follows – you had to drink a shot every time you saw one of the following:

  • A man wearing white pants and a pink shirt with a bonus shot if the collar was turned up
  • Any woman in skin tight capri pants, a designer tank top, and oversized sunglasses with a bonus shot if her plastic surgery scars were still visible
  • A toy dog being transported in a designer purse with a bonus shot if said dog was wearing a dress and/or sunglasses
  • An insanely skinny 30-something year old woman jogging like her life depended on it
  • One of Satan’s Minions (aka Hamptons Parking Enforcement Officers) marking tires with chalk
  • A Range-Rover honking its horn while threatening to plow over pedestrians or cyclists
  • A convertible Bentley. We had to remove this one from the list after the fourth one went by - one more Bentley and one of us was taking a stumble down the stairs later

Actually, we realized quickly that this entire list would lead to immediate and sudden intoxication and had to abandon the game altogether. We should have selected less likely options such as:

  • A 1994 Honda Civic
  • Lee or Wrangler jeans
  • A handbag small enough that it could not double as luggage
  • Real boobs
  • A woman over a size 6
  • A man in a wife beater tank top
  • Sneakers on anyone except an insanely skinny 30-something year old woman jogging like her life depended on it
  • Anyone eating at 6:00 p.m.

Oh, wait…that was us.

We weren’t really EATING…we were enjoying happy hour, so that made us less 60-year-old-couple-in-Sarasota-with-an-early-bird-coupon didn’t it?

Almond had a half chilled Maine lobster on the menu that had my name written all over it. Matt decided it had his name on it too, so we made it a double. Add to that a bowl of steamed mussels and it was definitely a happy hour.



With a couple of hours until sunset, we made our way to Sagaponack to find the Wolffer Estate Vineyard.

Sagaponack is a tiny hamlet near Bridgehampton proper that is known for its exclusivity, wealth, and, oh yeah, its farms. Didn’t see that one coming, did you? Despite the glitzy houses and impressive architecture, the area seemed surprisingly rural. There were farm stands, fields of wildflowers, and one of the areas favorite vineyards.


Wolffer Vineyards offers Sunset Saturdays through the summer, with wines by the bottle and live music on the lawn. The rosé seemed to be the favorite, so we grabbed a bottle and scored a table where we could sip our wine as the sun went down to the tunes of a local reggae band.




Children ran on the grass, couples strolled hand in hand, and twenty-somethings in expensive aviators and chic designer tank tops danced on the lawn. As the sun began to set…I finally understood what they meant by that “special light” that they have in the Hamptons.





For a moment, the world was literally bathed in a soft, golden glow. Beautiful people danced around us and the wine in my glass swirled to the gentle beat of the reggae band. Rows of vines were illuminated in the setting sun and I couldn’t imagine a more perfect place.




For all its high end glitz and pompous douchery, the Hamptons had won me over because, at heart, the Hamptons were just a dressed up beach town, simple and beautiful with lush green expanses, golden light, and the charm of any small seaside town.

They just had a better wardrobe.


It was 9:00 p.m. which meant it was now actually a proper time to eat dinner. Apparently showing up for dinner before 9:30 p.m. is like wearing white after Labor Day or driving a late model Civic.

You just don’t do it in the Hamptons.

Thanks to a recommend from TraceyG, we had reservations at one of Southampton’s summer hot spots, the Southampton Social Club (because I wouldn’t know Hamptons hip if it jumped up and bit me on the back of my non-designer jeans). Known for its lavish outdoor space and fire-pit adorned back yard, Southampton Social is where the young and hip go to see and be seen.


The fact that we were neither young nor hip did not deter us.

The interior was a series of chandeliered Venetian style dining room in what looked like a massive old house. It’s a restaurant until about 11:00 p.m., after which it becomes a hot night club. The restaurant opened on the back side to an expansive lawn strewn with tables and torches.

Since it was our 14th meal of the day, we opted to share a few small plates instead of getting a large meal, hoping that the waitress didn’t simply decide we were too cheap to eat.

It’s sad when you worry that even the wait staff will look down on you.

We ordered cocktails and braised short rib sliders with roasted strawberry barbecue sauce, cole slaw, toasted brioche, & gherkins; lobster rolls on buttery croissants; and an order of truffled parmesan pommes frites.



It was about 10:30 when we finished eating and we tried to hang around long enough to see the late night party, but the truth was….it was late and we were tired. So instead, we took our not young, not hip butts back to our cozy Water Mill cottage and called it a (very long) day.



We awoke to golden light slanting in through the white curtains and I had to give the Hamptons credit for that “special light” once again. It made everything seem soft and magical.


We headed the short distance to the Hampton Coffee Company for a cappuccino and a chocolate chip scone to fuel and early morning trek to the beach.





Going to the beach early seemed like a good way to avoid the lack of a “beach permit.”

Yes, you have to possess a permit to go to the beach in the Hamptons or pay a stiff $25 parking fee for the privilege of putting your toes in the sand for a few moments.

Even the beach was expensive in the Hamptons.



Not a fan of east coast beaches, with their dark waters and gray sand…..the beach surprised me. The water was a perfect shade of blue gray with a powerful surf that sent foam rushing toward the sand and bathed the horizon in mist. The sand was golden and littered with smooth round stones in every color. Large shells were scattered among the stones. The sand was cool and soft and the sky was bold and blue.








Like everything else in the Hamptons, what I expected to be overrated was genuinely special.

Before heading back, we took a short drive down the coast. Fields of deer, coastal ponds and bays lined with cattails and swans, and quaint churches made this place feel as unpretentious as any simple coastal town we’d ever been to.







This place was an oxymoron. It was simple, but luxurious. It was rural, yet cosmopolitan. It was laid back, while driven.

It was time for second breakfast, so we headed into Sag Harbor for brunch. North of Bridgehampton, Sag Harbor reminded me of coastal Maine. It was a proper village on the bay with the feel of full-time life, rather than summer visitors. It had American flags, white picket fences, and regular sized houses. It was more apple pie and less crème brulee.






We carefully checked the time on our parking meter, looking around at the abundance of parking enforcement officers, and made our way to Muse on the Harbor.

With a beachy beautiful interior and a breezy patio, Muse was a great choice. Primarily because they had peanut butter mousse filled french toast.



It was so good I want to say it again. Peanut butter mousse filled french toast. With a heap of bacon.


You probably just gained 4 pounds by looking at that picture.

After brunch, we strolled through the quaint streets of Sag Harbor. It was more old fashioned Americana than celebrity posh. Ivy climbed old brick walls, colorful wares were displayed in the window of the Variety Store, and a barber shop pole turned brightly in the sunshine.






We still had some time before the parking Nazis wrote us a ticket, so we headed to B Smith’s waterfront restaurant to sip a refreshing watermelon margarita and watch the boats bob in the harbor.






The watermelon margarita is, in a word, AWESOME. Light and refreshing, it was like summer in a glass.


With no real destination in mind, we started driving and decided to see if we could find East Hampton Point. We figured we could stop for some drinks before looping back through East Hampton to head to the airport that afternoon.

With sweeping marina views and a sailboat right inside the bar, this place was classy and luxe. Matt noshed on fresh oysters while I asked the bartender to mix me up something special. He came out with what he called his tequila berry mojito.




Berry good. (I’m sorry…I couldn’t help myself).

Sitting there on a crisp navy chair emblazoned with sailboats, looking out across the marina, sipping a cocktail in the sunshine, I could almost imagine that it was time to grab a bottle of Veuve Clicquot and head back to our yacht for a late afternoon nap.


However, when I snapped my fingers and said, “Godfrey, fetch my wrap…” no one came.

With some time to kill, we drove down to East Hampton. This is the village that screams “I have money. Lots of money.” This is where celebrities come to show off their mansions, strut their fashions, and fight for a table at Nick and Toni’s after spending a day shopping at Hermes and Tiffany.

We only had an hour left and it was going to be a long flight home, so we stopped to grab a late lunch/early dinner before heading to the airport. I chose the restaurant by one criteria alone: it was the closest dining establishment to the East Hampton airport.

This is not usually a good way to choose a restaurant and typically ends up in a meal at a Waffle House or a dingy Chinese restaurant that scored a 57 on its last health inspection rating.

I was pleasantly surprised when we walked into the bright and airy Highway Diner and Bar.


The restaurant was empty. That’s because only geriatrics and hillbillies eat at 4:00 p.m. in the Hamptons.




The artichoke bisque with bacon crumbles was divine.


The braised beef tacos were magnificent.


The fried oyster po’ boy was sublime.


And the “build your own sundae” with house made dulce de leche ice cream was inspirational.


It was time to lift off. Although I think we had spent approximately $50 per hour while in the Hamptons, it had been a great time. I got it. The “special light,” the expansive beaches, the charming villages….it drew you in, it held onto you, it made you feel welcome when you expected it to reject you like the head cheerleader in high school.






As we lifted off toward Westhampton airport, I gazed down at the mega-mansions, the rolling green farms, and the mirror-like bays scattered out to the horizon and hoped that one day, I’d be back.

Hopefully with a Bentley.






It’s not over until it’s over

And it wasn’t over.

Our client pushed the flight time back an hour and then was late arriving at the airport. Flying into the southeast on a summer evening gives you about a 99% chance of encountering at least one thunderstorm, or about 60 in our case.

We had to land short of our destination to wait out the weather. The plan was to land, sit in the airport FBO for a while, and then finish the flight despite the late hour.

At least that was the plan until the nose tire blew upon landing in Nowhere, VA at 9:00 p.m.

There was only one employee at the small hole-in-the-wall airport. One employee to shut down the runway and call the FAA. One employee to figure out how to tow the plane off. One employee to figure out what to do with us when the airport mechanic wouldn’t be in until the next morning and the closest hotel was a 30 minute cab ride away and Nowhere, VA didn’t have cabs.

As the guys wrangled with the plane, trying to figure out the best way to get it off the runway without completely destroying the wheel, I sat inside the tiny airport Googling Nowhere, VA to see where the closest hotel might be.

Indeed, the closest hotels were a good half hour away, as were the closest taxis. Not really a fan of $60 cab rides that I had to wait 45 minutes for, I looked to see what other options there were.

Google maps showed an Inn about 2 miles from the airport. When I asked the airport security worker about it he said, “No. There are no inns in town. I’ve lived here my whole life, and it’s a small town. There aren’t any inns.”

I showed him the map.

“Yeah…I don’t know about that,” he said. “I have worked at this airport for years and I’ve never seen that place even though it says it’s right down the street. That can’t be a good thing.”

We called.

They answered.

Creepy music began to play in my head.

We were not surprised to find they had rooms available. Probably because the previous guests were now buried in the basement. With the innkeeper’s mother.

The airport security guy dropped us off, shaking his head and saying, “I’ve never seen this place before. I’ll pick you up in the morning.”

It was an old house, which I am pretty sure was haunted, but I will admit that it was clean and cozy.

It was all the dolls that got me.


The house had an inordinate number of dolls. The big old kind. With the blinky eyes. There were dolls everywhere.

I suspected one might come alive and kill me in my sleep.


I was relieved when I awoke the next morning and did not see a doll standing next to my bed. Nose tire fixed, we took off in pretty gnarly weather, but only got as far as Roanoke before our positioning system went out. We had to declare an emergency and land.

It never makes you feel good when a fire truck and an ambulance are waiting for you when you touch down. While we were waiting for it to be checked out (I was pretty sure they were going to find a doll in there), we got weathered in.

Sometimes, it’s obvious God is trying to tell you something.

I decided he was trying to tell us to stay on the ground. Hello, Roanoke. We decided to stay for the day.

We eventually made it home. It was late in the day, and we were tired. Exhausted, but happy.

As I drifted off to sleep that night, happy in my own bed, I had visions of golden light slanting across a hazy vineyard, of smooth stones polished to round perfection by the pounding of a blue gray sea, of lush green lawns bathed in wildflowers, of the glow of a glass of rosé sipped at sunset…..and just as I began to drift into a sweet sleep I heard a final whisper….

“My name is Talky Tina and I am going to kill you…”

Next stop….the Twilight Zone……


Posted by vicki_h 11:07 Archived in USA Tagged southampton hamptons bridgehampton long_island sag_harbor

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Vicki, I always love when I see you have posted a trip report!! This one, like so many others made me laugh out loud. Hysterically. Love the doll story! Thanks for the chuckle! We are headed to key west in sept and I'll be checking your previous reports for some ideas!! Happy travels to you both!

by Twolittlebirds

OOH! So good to wake up and see another trip report notice in my inbox ready to read with my Cafe du Monde coffee~ 1. The Hampton's are beautiful 2.I could never afford the Hampton's so thanks for taking me there 3. I just gained 4 pounds (again) reading your report! Thank you Vicki~

by msgcolleen

Vicki, I enjoyed reading your blog. I do have few questions for you, how do I contact you? I would really appreciate it.

by Navy Wifey

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