What the Hamptons Was Like Back When

Since I’ve been in the Hamptons for such a very long time, people often ask what it was like in the early days. It sure was different from what it is today.

When I was a boy, there were no crowds of wealthy visitors, giant mansions, or horrendous traffic jams.

In fact, there were no roads upon which to have traffic jams, or at least no paved roads. We got around on horseback, in wagons or walking. Cars, a new thing, sometimes came through and raised a lot of dust behind them. You’d hear them coming. They’d backfire and spit. Scare the horses. These early cars could only be started by sticking a metal crank into a hole in the front and turning it clockwise. Cars would sputter and connect or not. If not, you’d crank again. The drivers sometimes asked us kids to turn the crank while they hit the gas, but we’d have none of it. There was a good chance you’d break your arm if the car coughed funny and the crank spun backwards at you.

All the grown-ups back then were fishermen or farmers. They made out well. Their best crops were potatoes and strawberries, or in the sea, striped bass, porgies and bluefish. Other folks waded out into the bays, clamming, catching lobsters or crabs. It was a good time.

I went to the Springs School. Today, hundreds of students are there. Back then, there were just 18 of us. I remember when baseball got popular. We’d play in the school’s front yard. Hitting the ball over the school was a home run. Babe Ruth came to our school once. He told us to be good and work hard. God loved us.

Nobody here ever went to New York City. Didn’t want to go, either. It was several days in a horse-drawn carriage to get there. Why go? It was good here. But, as I said, some city people, the rich ones, did sometimes come out here in their new cars. It would take them 10 hours and they’d complain about that. We called them “Thousandaires.” Later, “millionaires.”

Still later, the Hurricane of ’38 hit. It was the worst thing ever. It knocked down trees and buildings and cut new inlets into the bays. But it was nowhere as bad as the Hurricane of ’28, 10 years earlier. Cows flew during that hurricane. But we all agreed never to talk about it, and none of us ever did.

Today, there are hundreds of billionaires living in the Hamptons. But back then, there was just one. I remember him. A nice guy. His name was Horace. Built a big oceanfront mansion for his family in Southampton. At the time, there was only one historic old English windmill in the Hamptons. But he fell in love with it and went to auctions wherever windmills were sold and brought them back to the Hamptons. Eventually there were 11 windmills here. Still are. But then Horace got gout and died. We owe a lot to Horace.

I remember when George Washington, who ordered the Montauk Point Lighthouse built, came out to see it when it was done. He stayed with us at our house for two days. He had bad gout too. But handsome? Wow!

Teddy Roosevelt was another great person who came to the Hamptons back then. I didn’t meet him when he came. But years later, after he was president, he came back and I parked his car for him at a fundraiser and got to meet him. Really nice guy.

We had no television or internet back then. And only a few people had telephones. You’d pick up the phone and this operator lady would come on. She’d ask who you wanted to talk to. If they had a phone, she’d put you through. We didn’t have a phone, though. Dad said he didn’t want no operator listening in. If Mom or my sister or I wanted to see somebody, “Just walk over,” he said.

There was a famous Montaukett Native American I knew who, for a penny, delivered messages by hand to people in other towns if you gave him one. His name was Stephen Talkrunner. Later in life he slowed down and became Stephen Talkwalker. And then, toward the end, he stayed home. Wouldn’t deliver anything. We called him Stephen Talkhouse then. Today, a club in Amagansett is named after him.

We had famous artists, writers and musicians who came out here to live in the woods alone. So I never met any of them. Once a year in Springs they’d play a softball game. Called it the East Hampton Artists & Writers Annual Softball Game. I watched them play. But still didn’t meet any of them. The game gets played every August now. Sometimes thousands come to watch. It’s an event.

Today, houses in the Hamptons sell for millions of dollars. Back then, if a house got sold, it was for a dollar. Or maybe two. People could afford that. Today, not so much.

Marilyn Monroe lived in Amagansett one summer. I met her. Her car had a flat tire on the Napeague and I fixed it for her. She was nice.

Prohibition was a big deal for 13 years. Selling alcohol was illegal. But we locals got rich taking speedboats out in the middle of the night to meet the rumrunners, load up the crates of hooch, and motor them in at Montauk so these gangsters and bootleggers, who came out from New York City in big trucks, could pack them up and drive away with them. They paid a silver dollar a box. Life was good.

After that came the Depression. That was bad. My uncle Charley had a farm in Bridgehampton and on Sundays he’d load up the produce and bring it around to those less fortunate.

Then came World War II. That was really bad.

I remember one time when the men up in Riverhead in Polish Town held their annual fair, and afterwards went out to Mattituck to get into fights with the farmers at the Strawberry Festival there. They used to elect a Strawberry Queen every year. Maybe they still do.

In 1960, I started Dan’s Papers as the first free resort newspaper in America. And after that, the Hamptons became a world-class resort.

It’s not all been wine and roses, though. Hope I made that clear.