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Home » The Bridge Car Show: Another Year of Luxury in Bridgehampton
Luxury Cars

The Bridge Car Show: Another Year of Luxury in Bridgehampton

September 21, 2026No Comments5 Mins Read
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The Bridge Car Show: Another Year of Luxury in Bridgehampton
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A pristine 1950s navy blue Bentley Mulliner Coupe parked in front of Bobby Van’s on a Saturday morning was a reminder. Oh, right. On this particular Saturday more than 300 classic cars and one Human Carrying Drone were going to be at The Bridge. A high end car-nicopia of the finest old and new cars in the world. All spread around the golf course.

They start loading in at 6 a.m. Along with corporate sponsors like Mercedes Benz and Breguet timepieces. “There’s a very interesting legacy between Breguet and automobiles,” says Gregory Kissling, Breguet’s Global CEO. He shows me an antique tachometer. It’s part of an elaborate pop up showroom. “It’s all about performance and precision, in the watch industry and in automobiles.”

Breguet timepieces, Photo: Bill MCCuddy

Performance and precision, sure. But there’s also a bus, a daytime drive-in, a jazz band and a gaggle of yellow Porsches all pretending to be taxi cabs. The kind that, if they did exist, might bring you here.

Michael DiSpirito from Upper Brookville brought a Ferrari last year. He’s back for the food and, of course, the cars. “They’re displayed perfectly here. It’s a combination of cars, food, people and drink.” And then he’s off to see something called a Ferrari SF90 XX. “It’s beautiful and 1035 horsepower.” He would know. In fact there are a lot of “car guys” here. Women too.

Rebecca Rose Woodland's Mercedes 300SE convertible at The Bridge
Rebecca Rose Woodland’s Mercedes 300SE convertible, Photo: Bill McCuddy

“My favorite vintage car was a Mercedes 300SE convertible,” says Rebecca Rose Woodland. She is a lawyer with a place in Sag Harbor and a regular legal expert on television. Mercedes brought a bunch of classics. They’re in the restoring business now. “The lobster roll was as standout and the jazz band and concert pianist gave a car event a different flavor,” she added.

1950s Jaguar with a custom bubble top over the driver's seat at The Bridge 2026 car show
1950s Jaguar with a custom bubble top over the driver’s seat, Photo: Bill McCuddy

She’s not wrong. This has been a truly unique event for 10 years, and the crowds, cars, food and entertainment grow bigger and better every year. Some of the proceeds send Harlem students to college. “It’s the best event of the entire season in the Hamptons,” Peter Ostrega of Sag Harbor sys. He and I are standing next to a ’50s Jaguar with a custom bubble top over the driver’s seat. “It looks like a space ship,” he says. The Bridge tops everything else for another reason. “This is the highest point on Long Island, I’ve been told, so the view is incredible.”

Joseph Barra with his 1972 Corvette
Joseph Barra with his 1972 Corvette, Photo: Bill McCuddy

But maybe the hit of the show was Joseph Barra from Fishkill, NY who brought (and sat proudly next to) a 1972 Corvette. “I’ve had for 44 years.” Uh, he’s done a little modifying. “It’s been through four color changes.” It’s purple “with metal flake” now. But he’s burying the lede. The engine is a 502 motor that sticks three feet out of the hood with “24 karat gold plating and 703 horse at the crank.” I don’t know exactly what that means, but this guy looks and sounds like he won the lottery to be here. Everyone he talks to gets the same feeling.

The Bridge 2026
The Bridge 2026, Photo: Bill McCuddy

Later in the afternoon, my daughter Lilly excitedly asks me if “I met the cool retired guy with the giant motor in his car?!” I did. He brought it on a trailer like many of the show cars here. Does it drive? “Oh yeah, basically I take it out, scare the crap out of myself and put it away.” Well said.

The big drone was, appropriately enough, taking off and landing from the driving range. I don’t think they were giving rides and I didn’t ask. I got queasy just watching it. But the food stalls were all first rate. Mercedes had caviar and crème fraîche on potato chips. Hennessy Cognac was being poured next to the drive-in. There were also fancy clothes manufacturers and a cool Volvo photo booth where the photographer was directing people like Coppola. “Now look up and laugh!” I did.

The Bridge Sunday Cars & Coffee gathering
The Bridge Sunday Cars & Coffee gathering included some rain, Photo: Bill McCuddy

The next day, two events — one a “Cars and Coffee” gathering behind the Community House in Bridgehampton, and the other, a mini car show and brunch at Topping Rose — were both weather challenged. But with tops up and umbrellas at the ready, the shows went on. Debbie Srb is a Sotheby’s Realtor. “I had an amazing time both days. I’m a car enthusiast myself. My brother brought a Porsche 911. Not one of the taxis! They were great.” And then she adds shrewdly, “Cars and real estate cross over.” Yep, everyone needs a garage.

Cars on view Sunday at Topping Rose House, The Bridge 2026
Cars on view Sunday at Topping Rose House, Photo: Bill McCuddy

By the way, the Bentley I saw that morning on the street in Bridgehampton? It wasn’t part of any show. It was driven, just like the rest of us, to the parking lot off Scuttle Hole Road where the owner got on a shuttle.

It was that kind of weekend.

Bill McCuddy The Bridge Aston Martin
Our intrepid reporter is standing next to a 1960s Aston Martin Drophead Coupe like 007 thinking, “My name is McCuddy…Bill McCuddy.” Let him dream

Bill McCuddy worms his way into fancy stuff and then writes about it. If we don’t think there’s a lawsuit pending, we print it. He has owned a few “cool old cars” but now spends most of his time “on a million dollar stretch called ‘The Jitney’ going back and forth to Manhattan.” He is a film critic on PBS and has a radio show “Air Hamptons” on WLIW-FM. 

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