Watching The East End Change One Decade At A Time

Technically, I am moving in as a 30-year guest in the Hamptons. I lived year-round as a resident for about ten years before I got married and moved up Island with my wife. But I still keep my sailboat in 3 Mile Harbor, which means I visit the Hamptons 70 to 100 times a year.

After coming to the Hamptons by accident, I stayed for 10 years, making a living writing and other odd jobs to pay child support and things like that. As often happens with older people money from family investments were cashed in, and I had a bit of a buffer.

But this is not about me. This is about the changes I have observed in the Hamptons starting with the businesses I wrote about and the people I wrote about whoever either passed or went out of business and the new businesses and new people that have come to take their place.

Between 2005 and today, in 2026, I have witnessed an old guard of people dating back to World War II who struggled and eventually made money via real estate, who either died, or sold, their land, and left. Period. Then there were the businesses that thrived until real estate rents forced them out of business. And lastly, there are the others who have thrived and are now almost equal to the south of the highway elites.

As far as real estate and things like that, you would have to say that the East End is in stronger hands financially, with very few people hanging on by the skin of their teeth, and most homeowners are at least minimally millionaires.

Unfortunately, except for the businesses that own their buildings, the opposite is true, where most businesses are hanging on by the skin of their teeth. It is sad to see so many familiar faces have to call it quits.

Being a man in his 70s, I am not going to talk about the prices of food and so forth because over a lifetime, they go up and it is always shocking when you think about what things cost when you were much younger. However, I have noticed that patterns of spending money on things like food and restaurants have changed as the prices have risen. For example, there used to be three or four sittings per evening for restaurants, and now it is basically down to two. Yet I do not think you can get a tasty dinner for less than $100 per person these days at any restaurant.

I believe this means more people are eating at home more days a week, or they are eating sandwiches and things like that, and not going to the restaurants like they used to 20 years ago.

Not quite sure if I am qualified to speak about the summer social scene that I used to report on but never really was a member of. Period. I just noticed that the focus of such events has changed and yet has remained the same after all these years. The same can be said about fashion. But I was never really qualified to talk about fashion.

One trend I have noticed is that the young, really rich do not seem to be choosing the Hamptons or the east end of Long Island to buy their second homes or visit as much as they did perhaps 25 years ago.

I will never bet against Hamptons real estate after watching every home and parcel of land increase two/three fold since I arrived but there is another hiccup occurring now just not as bad as 2008-9 or 2018. Maybe it’s just my 1960’s Woodstock mentality but I see a sea change. Locals will always live here, it is what hometown folks do. They know how to mine the gold from second home owners and summer tourists, but the vibe is different. I suppose the love of fishing that brought my grandfather and dad out east for fishing trips will never die, but will it grow? It’s no secret private boat traffic is down our in the bays and oceans with availability at marinas.

Maybe it’s just my perception changing but I do believe there is a real change happening on the East End of Long Island.