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How my parents taught me to party in the Hamptons

Aisling and her parents in the Hamptons
Aisling and her parents in the Hamptons

The actor Liev Schreiber is walking towards my mother. Or, rather, the actor-plus-entourage is walking towards the private event happening behind our table and my mother’s chair is in the way. Entirely unflustered, Mum offers her hand as he approaches, as if Schreiber would deem this a singular honour, and tells him she loves his films. He nods, shakes, smiles, says thanks and moves away, his entourage packed tightly behind him.

“He was in my eyeline,” she says. “It would have been rude not to.”

We are in Surf Lodge, one of the Hamptons’ – and specifically the hamlet of Montauk’s – hottest party spots. The sun is setting, hip hop legend Questlove (frontman of The Roots, the in-house band for The Tonight Show with Jimmy Fallon) is on the decks, and the people at the table next to us are ordering cauldrons of cocktails while a waiter manoeuvres a $1,250 (£1,050) Imperial bottle of cult rosé Whispering Angel towards another group.

In fact, the service around here is abysmal, but the crowd doesn’t seem too concerned. “People don’t care about what’s in their glasses or on their plates as long as they’re here,” a staff member confirms.

Aisling as a baby at a party in the Hamptons
Aisling as a baby at a party in the Hamptons

My parents love a good party – and here was a chance to reminisce about their days living it up in New York and the Hamptons when they left Ireland in the late 1980s. Dad went over first and Mum followed a year later, just two out of a “Generation Emigration” seeking better opportunities.

I feasted on their stories while I was growing up, like the one about their friend who showed up with a Rolling Stone, who then drove someone else’s car home. Or the grand piano that someone had won in a bet in a bar in Midtown Manhattan and brought out to the house for some singalongs. Fun times. Glamorous times. Times I’d decided to recreate myself for my 30th birthday, with my parents along for the ride – to give me pointers on how partying should really be done.

With Dad at the wheel, Mum by his side and me lolling in the back seats, we drove from JFK to the South Fork of Long Island, where moneyed Manhattanites decamp from the sweltering city, creating a sort of New York-by-the-sea between Memorial Day Weekend at the end of May and Labour Day at the beginning of September.

Thirty years ago, my parents made the trip each season to a summer time-share property. Like one-time Vanity Fair and New Yorker editor Tina Brown, they rented in the part of the Hamptons closest to the city. And while Brown was entertaining New York’s movers and shakers in Quogue, my parents were just in the next hamlet over, hosting Gatsby-themed garden parties in Westhampton. Some years they had more than 500 guests during the summer.

Plum Guide's award-winning architecturally designed house made a dream base
Plum Guide's award-winning architecturally designed house made a dream base

Thirty years on, according to Dad, the traffic to get there is just as bad as it ever was.

The Hamptons “scene” began in the early 20th century, when rich families started capitalising on a new concept called “leisure time”. According to Richard Baron, former chief curator of the East Hampton Historical Society, during the Jazz Age East Hampton’s “dunes and old barns were filled with the spirits that kept the mood of the Roaring Twenties soaring”. Despite Prohibition, the booze still flowed, with Montauk a big rum-running town in the 1920s. A century later and the Hamptons found itself facing another alcohol shortage: champagne. A Russian billionaire, aghast at such rations last year, flew in 15 cases of bubbly on his private jet from France for his wife’s annual Hamptons birthday party.

Such ostentation now sits rather awkwardly, particularly in the aftermath of the Russian invasion of Ukraine and a stratospheric rise in the cost of living in the US and beyond. But the Hamptons have always been about stepping out of reality and into a gilded world, a bubble where real-life concerns are left behind. A bubble where Soul Cycle has taken over a barn and Cartier has just opened its first pop-up.

For the first few days, we stayed in East Hampton, the oldest of the seaside hamlets. This was the site of the renowned White Party hosted by P Diddy on Hedges Bank Drive that kicked off in 1998, sponsored by Veuve Cliquot, where Paris Hilton and Martha Stewart rubbed shoulders for the night. The dress code was so strict that Janet O’Brien, who catered for the event, remembered having to bring extra white tablecloths so that people could dress themselves if they didn’t arrive wearing white. “I had to arrive with extra white chef pants too,” she recalled.

Parties aside, the Hamptons must-have is a house in which to host them; hotels are few and far between. From the beach house of my memories to the shabby-chic cottage of the Sex and the City gang and Diane Keaton’s oceanfront spread in the film Something’s Gotta Give, property is key in these parts. For our own pad, I turned to Plum Guide, an upmarket holiday let company, and when we arrived, I knew we’d all fit in nicely: it was as if Aidan Shaw (Carrie Bradshaw’s trendy carpenter boyfriend) had created the award-winning architecturally designed house himself.

First things first: an evening on Shelter Island. Until recently, this wasn’t regarded as a party place (it has a population of 3,253, is supremely unflashy and locals see it as totally separate from the Hamptons), but ever since Andre Balazs set up Sunset Beach in 2012, the hotel has been getting a name for itself as a place to be. With the DJ playing as the sun set and people nursing their drinks at the outdoor tables and the fire pits towards the back, there was certainly a buzz. Value for money was in short supply though: the tiniest burrata I’ve ever seen arrived at our table for $30.

Montauk, on the other hand, has long been the place to be, starting with Andy Warhol and Peter Beard’s parties in the 1970s. Flash forward 50 years and Surf Lodge is infamous for its legendarily long bathroom line. By day, there’s an older crowd around here that steadily gets younger as the night wears on, with many migrating over to live music venue Stephen Talkhouse (still going strong at 2am).

Surf Lodge is one of the Hamptons' hottest party spots
Surf Lodge is one of the Hamptons' hottest party spots

Later in our stay we returned to the source of all our family memories of the Hamptons: the cedar house where my parents hosted their gatherings. Sadly, the once-virgin lawn was taken up by two other properties, a sign of the enormous real estate values around here. The party was certainly over now, as confirmed when my mother tried to order an Aperol Spritz at a local bar: they’d run out of Prosecco at the weekend.

The Hamptons may be a throwback to a more gracious past, but they aren’t immune to the passing of time. Where once artists, flappers, and oil barons came to dance and debauch, now the clientele are internet billionaires, influencers and finance experts. My parents’ time here was part of that continuum and now their own time at the epicentre of New York glamour has slipped away. Post-9/11, post-Gossip Girl and post-pandemic, the Hamptons has become rather a victim of its own success.

On our way back to the airport, I asked them both: “Shall we do this again in 30 years time?” My parents looked at each other, quickly doing the maths. “Hopefully by then you can drive,” Dad said.

Plum Guide (020 3795 1390; plumguide.com) offers seven nights in the Hamptons from £451 per night.