Famous in the Hamptons: Billionaires, Beaches and...Car Racing?

The Hamptons is famous for many things. The most well known are, perhaps, the fabulous beaches, which are among the most beautiful in the world. It is famous as a summer resort for the wealthy. It is famous for its beautiful colonial New England villages and its 18th century wooden windmills. It’s famous for its fishing—Montauk holds more world records than any other town in the world. And the community is famous for its artists and writers, its film and TV celebrities, its wineries and its agriculture. There’s even a famous old whaling village out here.

But did you know that the Hamptons has a long tradition with automobiles? From 1915 to 1921, cars raced on dirt roads through the wooded and farm-field landscape of Bridgehampton. In the early 1930s, high speed racing car drivers held events out at Montauk, where a legend of the racing car fraternity—Carl Fisher, a man who held the land speed record for a while—created a racetrack out of a curvy residential road called South Fairview Avenue. There’s old footage of those races there. And then in the early 1950s, racing cars returned to the streets of Bridgehampton—including Main Street for four straight years, until the State of New York made it illegal to do that. As a result, in 1958, racing enthusiasts built a big Le Mans style track with twists and turns and straightaways north of downtown Bridgehampton. Here, for more than 20 years, the legends of racing—Dan Gurney, Bruce McLaren, Richard Petty etc.—competed in races with cars going nearly 200 miles an hour at this track—The Bridgehampton Racing Circuit.

Today, these racing venues are a memory. And some of the cars of those eras, together with the regular private automobiles of those eras—the Model Ts, the Packards of the 1930s and 1940s, the European sports cars of the 1940s and 1950s, and the tail-finned giants of the 1950s and 1960s, are collector’s items.

You may know that today Jerry Seinfeld of East Hampton has a Porsche collection, or that other millionaires and billionaires have old vintage cars they keep out here. But you probably didn’t know that the Hamptons is among the few places in America where vehicles such as these are garaged in places where they are polished and cleaned and started up regularly and monitored 24 hours a day with video cameras. A man (or woman) who wants to pay the price can have a set-up where he keeps a live video in a frame on his desk at his New York office, which shows his precious car being tended to. Some of them are worth millions.

And then there is the annual Bridgehampton Road Rally and Tour d’Hamptons. On a particular day once a year, all these cars, as many as a hundred of them, are brought together for a day of celebration and low speed rallying. This has been going on since 1993. And this year, the day was Saturday, October 7.

That morning at 8 a.m., I walked out and opened the overhead door to the single car garage on my property in East Hampton to see if I would be able to attend. Would it go? Could I get it started?

The vehicle in question I own was built in 1959 in England. It is a small, bright red sports car called a Triumph TR-3. In 1967, when I was 28 years old, I had bought it from a man who owned a bar in Hampton Bays for $600. And I had driven it home. It’s been in my garage since. And on sunny days, I take it out for a spin. Sometimes. If I can get it to go.

On this morning, I climbed into the driver’s seat, pulled out the choke, tapped the gas pedal a few times to bring up the gas, turned the key and pressed the starter button.

Yes, it has a starter button. It also has a hole in the grille where, in an emergency, you can insert a steel crank and turn it hard a few times to get it to start. I have the crank. I’ve never used it. I also have the log book that my friend in Hampton Bays wrote in, describing oil changes, tire switching, regular engine maintenance and places this vehicle was driven to during its first few years.

The starter motor turned and tried to get the engine to catch and pick up the cadence. It wouldn’t do it. I stopped. Went through the procedure a second time, then a third time, and on this try it worked. Then I had to sit there in the cockpit continuously running the engine with the choke on and my foot on the gas so it wouldn’t stall out. I watched a gauge on my dashboard as I did this. When the temperature of the engine reached about 140°, I was comfortable with it. I could push the choke in and ease down up the gas. It rumbled in appreciation. It would go. And so, with my stick shift, I put it into reverse and slowly made my way out of the garage, down the driveway and out to the street.

Yup. I would be driving this old car to the Road Rally. Maybe. The engine has a knock you can hear when you step on the accelerator. It’s a bearing in one of the piston rods. The engine is in need of a repair and I will have to get to it soon. But I think I can make it to Bridgehampton. If I take it easy.

What a beautiful day this was. I got there. The cars of all us car buffs assembled in a big field behind the Bridgehampton Museum. We lined up in rows where the parking crew ordered up. I wound up next to a 1957 Jaguar on one side, and a 1949 Jeep on the other. People wandered over. Some had just come to look at this wonderful collection. But others had brought something of their own.

“We heard that thing knocking when you came in,” one fellow said to me as I emerged from the cockpit. “Are you going out on the Rally?”

The Rally would be heading out at noon, a driver and navigator one at a time, at one-minute intervals, to proceed in these “vintage” cars on the secret route—it is different every year, and revealed only to the registered cars on Rally Day—through the Hamptons. There was a map of the 70-mile route. They’d stop at places along the way where volunteers would be to handle the time you came through. There were four different locations where you’d have to get out of your car to come up with answers to trivia questions. (This year the topic was baseball.) The rally would take all afternoon.

“Nope,” I said. This was not for a car with a bad bearing. But I was going to go on the Rally Day Parade, at 11 am. This was a four-mile parade of cars along the route around town that followed the high-speed racing going on in the 1950s, before the New York State made it illegal. That I could do. Maybe.

It was a beautiful autumn day in the 70s. A huge tent with a stage was alongside where all the cars were lined up in their rows. And here, you could check in, enjoy a breakfast courtesy of Union Cantina, get a Golden Pear box lunch for the rally if you were going off on it, listen to the Bridgehampton High School band and then later the music of Jim Turner and Paul Scollo, enjoy conversations with car buffs, buy souvenirs, enter a silent auction and a trivia contest with the experts from carshowsafari.com, watch videos of the old Bridgehampton car races, see the latest new cars from Southampton Audi, Porsche, Jeep and Dodge, listen to essays read aloud about cars by those who wrote them at an official Dan’s Papers Literary Salon there, and, when the Rally and Tour d’Hamptons people returned late in the afternoon, sit and enjoy the awards ceremony.

What a nice way to spend a day.