Ken Jockers and his husband, David, will not only feel the pinch of the soon-to-go-into-effect congestion pricing—they have to, in essence, look at it every day.

“We see a new big streetlight-looking thing that goes up and across the road on Central Park West and 60th Street with sensors,” Jockers says. “We shake our fist at it.”

Beginning in June, those sensors will automatically charge motorists as New York City’s Central Business District Tolling Program introduces a congestion-pricing program that will require passenger vehicles, trucks, motorcycles, taxis, and other for-hire vehicles to pay a toll upon entering the area below 60th Street. With an E-ZPass, fees range from $36 per large truck to $15 per passenger vehicle and $1.25 per ride for taxis and will be enforced from 5 a.m. to 9 p.m. on weekdays and 9 a.m. to 9 p.m. on weekends, with significantly lower rates overnight. The city hopes that the program will “result in 100,000 fewer vehicles entering the zone every day, relieving crowding in what is today the most congested district in the United States” as it implements the first program of its kind in the country.

The real pain for Jockers isn’t that the sensors are an eyesore, it’s that the couple will be clocked by them when they drive from their modest Columbus Circle apartment to their modest house in Montauk most weekends. Since they live on the border of the toll perimeter, and park on the street on the Upper West Side, they could conceivably end up paying $15 in and $15 out. While acknowledging it’s not quite as taxing as the fee will be for someone who lives in a rent-stabilized apartment within the zone and depends on their car for work (however, the MTA notes that households whose “adjusted gross income is under $60,000 may qualify for a tax credit in the amount of tolls paid”), Jockers maintains that it is “significant money” for the couple. Still, he says, driving uptown to pay one bridge toll to save on another makes little sense. He doesn’t think it will have any impact on the wealthier people going back and forth from the Hamptons either.

“It’s people who pay $24 for a bunch of asparagus,” he says. “They’re going to try the first couple of times to avoid it, but then they’re going to forget about it and bring their car into the zone.”

That means if it was the MTA’s intention to thwart driving into Lower Manhattan, it has met its match in the moneyed people of the Hamptons.

“Are people going to stop driving in? No,” says one East Hampton resident. “It sucks. But nobody I know cares.”

“It won’t deter me,” says another.

That’s because $15 per trip is inconsequential to those with second homes on the East End. Most of their support staff is local, or in the case of summer nannies, bused in or there for the season. Weekly drives back and forth along the Long Island Expressway, trying to game traffic, are an accepted part of the summer ritual. Like Jockers, many want to know if the upper level of the Queensboro Bridge, which feeds cars onto East 62nd/63rd Street, counts as out of the zone. (It does.) The lower level puts cars inside the zone on 58th.

Even though most habits and bottom lines aren’t impacted, Hamptonites are not happy.

“I’m pissed,” says one East Hampton homeowner with an apartment below 60th Street who asked not to be named. He and his family go back and forth year-round and see no way of avoiding what he thinks is a ridiculous fee. “We are paying for fare beaters and mismanagement of the MTA budget. They should charge the electric bikes. They get around faster than cars because they don’t follow any traffic laws.”

One woman who splits her time between her Gramercy Park apartment and Amagansett house has her “status greens” to consider in her commute. “I wish I could drive out there Memorial Day and stay until Labor Day, but this ain’t 2020 anymore,” she says. “I really can’t bring all my CSA produce back into town on The Jitney—I’d need to buy a second seat.”

Even those who live above 59th Street and can avoid the fee by crossing the Throgs Neck or Robert F. Kennedy bridges have another gripe. One Upper East Side resident who plans to adjust her Hamptons commute to avoid the toll thinks everyone else will too, pushing the problem into her neighborhood in the city. “If there’s a way to avoid congestion pricing there, then it will create traffic.”

Of course, there are other options for getting back and forth besides driving one’s car. There’s the new bus service offered by Blade, the Hamptons helicopter company. Blade is apparently banking on money being no object for its riders, who could easily avoid the $15 toll by paying up to $275 each way for a luxury bus ride to the beach. And for about $1,050 each way, Blade flies patrons in around 40 minutes, longer if it’s windy. Those who take the chopper love it but say it’s not without risk. “If there’s bad weather or Biden is in town you are screwed,” says one regular flier. Still, she thinks more people will take advantage of the service now because of congestion pricing—as in spend $1,050 to save $15. Out of principle. “The congestion pricing adds insult to injury. Just the idea is annoying.”

For those not interested in cutting off their nose to spite their face, there’s also the Long Island Rail Road, which runs from Penn Station all the way to Montauk several times a day for less than $32 during peak hours. And there’s the Hampton Jitney, a bus line that used the Queens Midtown Tunnel some 20,000 times in 2023, and depending on the ticket type, can cost up to $72 for a one-way trip.

Earlier this year, it appeared as though the privately owned bus company would have to pay the full freight on congestion pricing since it wasn’t on a government contract and exempt. The company called on its ridership to help fight the fight, and won an exemption from the MTA, which clarified that commuter buses like The Jitney wouldn’t be charged.

Judging by the enthusiastic response to the victory in almost every East End local paper and digital publication, it was as though the Hamptons had been awarded free rosé for life.

“Jitney scores exemption from MTA congestion pricing fees,” read The Suffolk Times.

“MTA Announces That Hampton Jitney Will Be Exempt From Congestion Pricing,” wrote 27East about the “good news.”

“Hampton Jitney Gets a Break,” declared The East Hampton Star.

But even people who already take The Jitney on the regular aren’t happy about the new city fee. Year-rounders savor the quiet of off-season ridership.

“The Jitney will get more crowded during the week and in the winter. It’ll end up being as busy as in the summer,” says Denise Gale, a local Springs artist who frequently goes into the city to go to galleries and museums. “It will be a pain in the ass.”

Nobody is poised to be more put out about the congestion pricing than the freeloaders who depend on rides from their New Jersey parents or friends with second homes in the Hamptons.

“The fee means I won’t be picking up any friends on the way out!” says one such person. “Or cutting through NYC from Hoboken. I’m sure my daughter hasn’t been thinking about that!”

Correction: A previous version of this article associated Mayor Eric Adams with decisions around congestion pricing; it is an MTA program that he did not create.