The Hamptons Wasn’t Always the Hamptons: BODIES & BOTS #23

“Oooh…you’re going to THE HAMPTONS!” declared some of my Arizona friends.

What they don’t realize is that this part of the world was a simple fishing village back in the 1950s when my parents honeymooned there. It’s an area steeped in history.

When I was about eight, my parents loaded me and my brothers into our Buick Skylark and drove out there for vacation. (Here’s the photo to prove it!) Like many areas of the country, it was “discovered.”

But timeless pockets of history and good people remain.

First, a short history lesson:

Before the Limelight

The Shinnecock and Montaukett peoples fished and farmed here for thousands of years. European settlers arrived in 1640. By 1648, East Hampton (formerly Maidstone) was established. The economy: whaling, fishing, farming. 

The fishing families of Springs and Accabonac Harbor became known as “Bonackers.” Polish immigrants built the North Fork’s agricultural community. Long Island once had 100,000 acres of farmland. Today: 36,000. 

Artists Abounded

• Pollock and Krasner moved to Springs in 1945. The barn became the studio where drip painting was invented.
• De Kooning built his Woodbine Drive studio in 1963. “It would be very hard for me, now, to paint in any other place,” he said.
• Steinbeck lived in Sag Harbor. Plimpton, Matthiessen, and Albee were Guild Hall regulars.
• The entertainers followed: Seinfeld, Stern, Billy Joel, Paul Simon, Ina Garten, SJP, Spielberg, Beyonce and Jay-Z.
• Stephen Talkhouse in Amagansett has been hosting live music since 1970.

Then came the finance and tech crowd. Technology doesn’t just change how we work. It changes where we live, what we value, and which communities thrive or struggle.

The Money Arrives. And Arrives

Two disasters rewrote the demographics. Hurricane Sandy in 2012 drove people from beach towns in New Jersey to the Hamptons. The pandemic in 2020 did the rest. The city emptied. The summer address became permanent. For decades, people had to live near their jobs. Suddenly, many didn’t.

The median Hamptons home price crossed $2 million in 2025. East Hampton Village: $5.6 million. Bridgehampton logged over a billion in sales in a single year.

A place shouldn’t just be defined by who can afford to buy property there. It’s defined by the people who make it work.

What Survives

Deep Hollow Ranch in Montauk is still the oldest cattle ranch in America. The Talkhouse still books bands (but now has its own hard seltzer brand). Writers and artists are still here. But only if they got in early or made it big.

And yeah, me.

I’m here.

60+ years later, and this is still my place of peace and creativity. But now I have wifi, AI, and a nearby podcast studio.

Everyone has their “drip painting” tools.

P.S. This week’s retreat includes producing Chapter 3 of YOUR NERVE. More soon.