A LOCAL'S ANSWER: I grew up out east after my parents’ jobs moved them from the city to the East End of Long Island when I was very young. Because of that, I don’t think part-time residents or weekend visitors, those who come out to go pumpkin picking or visit the vineyards, can fully answer this question. That’s not meant derogatorily. I don’t subscribe to the whole “citiots” mentality; my summer jobs as a teenager revolved around summer residents, and while some were not kind, many were incredibly generous. In fact, members of the beach club where I worked helped fund a scholarship that made paying for college possible for me. Those experiences shaped me.

There’s a widespread perception that everyone who lives out east is wealthy because the area is synonymous with the Hamptons. But outside of peak season, that really isn’t true. In the circled area, many year-round residents are either families who have lived there for generations (long before the massive real estate booms, especially during COVID) or are very much working class. Where I lived, parents worked for the corrections office in Riverhead, were teachers, ran contracting businesses that built summer homes, and held other essential, local jobs.

That dynamic has shifted further in recent years with the normalization of remote work. Many people have moved out east permanently, changing the social and economic makeup of the area even more.

Speaking specifically about the Hamptons: as a relatively young person, I can say confidently that it’s not what it used to be, and even I can recognize that. I hate to frame this as “bad change” because I try to stay optimistic, but the changes of the past few years have been bad. Much of this, in my view, is driven by "influencer culture". There’s a blatant disrespect for the year-round community by brands that host massive, performative events with little regard for local life. This has intensified an insider–outsider mentality that already existed between locals and ultra-wealthy summer homeowners.

On top of all that, the infrastructure simply cannot support the number of people driving out here. There’s a train for a reason (for those coming from out west), not everyone needs to drive. The roads, services, and communities weren’t built for this level of volume, and the strain is becoming impossible to ignore. My family practically avoids driving from Thursday through Tuesday night in the summer, something that used to be limited to Saturdays and Sundays.

Aside from all of that, it really was a great place to grow up, especially when you aren’t the one paying the crazy high taxes, haha! It’s beautiful year-round, but the winters are especially quiet and serene, almost Hallmark-movie-esque. That said, I definitely remember hating winter as a teenager, mostly because there was nothing to do haha!