I'd been driving for almost three hours when I saw the license plate signalling my time in the car was almost over: an abbreviated spelling of Water Mill, a hamlet in Southampton.
I spent the notoriously busy Labor Day weekend in the Hamptons, and though I knew to expect a wide variety of wellness options and expensive groceries, other aspects of the East End stood out.
Tension simmers not so far under the surface
The Hamptons is well-known for a tremendous concentration of wealth, but not everyone visiting over the weekend supported the uber-rich.
On Sunday, a small group of protesters gathered in East Hampton as part of a nationwide "Workers Over Billionaires" campaign. Some gathered at an iconic restaurant; others targeted the home of the billionaire hedge fund manager Bill Ackman. A press release for the event said protesters wanted to "confront billionaire donors reshaping New York politics," referencing the city's coming mayoral race, with the policies of the frontrunner Zohran Mamdani having spooked some wealthy residents.
Houses were also a source of conflict. Two luxury real estate agents in the area told Business Insider that some residents were grumbling about a recent change to the East Hampton zoning code that limits the size of new houses. Local news talked about existing properties, though — an edition of the East Hampton Star featured an article about water usage in the area, noting that some homes pump millions of gallons of water yearly.
It's more family-oriented than expected
Many know about the Hamptons nightlife, but I was struck by how family-oriented the area seemed, even on such a busy weekend. I saw more kids with ice cream cones than I did drunken clubbers, at least out in public. Kyle Rosko, a real estate agent at Douglas Elliman, told me most of his buyers are families.
That's not to say there wasn't drinking or partying — lines at the infamous Stephen Talkhouse, for example, stretched down the block.
Remote work changed things
I knew crowds would swell over Labor Day, but I saw firsthand how stark the difference is between midweek and the weekend. The Hampton Classic Horse Show was fairly empty when I visited on Wednesday, but an employee at a food stall told me crowds surge on the weekend.
In Montauk, lines stretched out the door at local coffee and breakfast spots over the weekend, but I didn't see any crowds when driving through on Tuesday morning. The same went for Amber Waves, one of Ina Garten's favorite farm stands — there was hardly a wait on Wednesday, though customers snaked through the aisles late Sunday morning. I wasn't shocked, but the difference was more striking than I expected.
Dana Feller, 52, a cofounder of the homeware brand Hamptons Blue who lives in Water Mill full time, said she'd seen remote work affect the pacing of each week.
"A lot of people come out here now on Thursday and then stay some time through Monday, and then they're in the office Tuesday, Wednesday, Thursday," said Feller, who has been coming to the Hamptons for 20 years but moved here permanently during the pandemic. "As opposed to it being a Friday to Sunday, it's now a Thursday to Monday."
By the time I left on September 2, the summer season had officially ended. One waitress at a popular Amagansett spot told me she would head to Colorado to work for the winter ski season; a valet at a Montauk restaurant said they were getting ready to shut down until next year.
The natural beauty isn't all natural
As picturesque as many of the multimillion-dollar houses are, the landscaping sometimes caught my eye more than the architecture. Hedges are cut at right angles or in perfect bulbs; hydrangea bushes are trimmed to reveal perfect end-of-summer blooms.
Nature is far more unruly, though, than the estates suggest, and evidence of the work required to maintain the landscape is everywhere. Vanity Fair reported in 2023 that some residents spend hundreds of thousands annually to maintain their lawns.
One morning, I heard two employees from a groundskeeping business talking in front of a house in Amagansett about "fixing" the landscaping chaos (to my untrained eye, the lawn looked pretty good). Landscaping trucks dot the shoulders of local roads, and it's easy to notice them given how slowly traffic often crawls.
