What It’s Really Like to Grow Up Where the Ultra-Wealthy “Summer” — And Why I Left

When you think of living in the Hamptons, what comes to mind? Maybe you think of pool parties, celebrity sightings, and Ina Garten’s picture-perfect shingle-style home adorned by bushy flower beds. As someone who grew up there, it evokes the feeling of sandy soil beneath my feet and the northern cardinal’s song. I think of the first warm day of spring where 60 degrees feels like a godsend after a long winter, and the sun seems to come out of hibernation to beckon everyone outside for their workday lunch. 

Growing up in the Hamptons is a very different experience to summering in the Hamptons. In fact, locals don’t use summer as a verb at all. Here’s what my experience has been like, growing up there for 26 years — and ultimately moving out west.

Typically I avoid telling people where I’m from. Especially now that I live on the West Coast, the perception of the Hamptons is so different from my childhood and young adult experience that I’d rather just tell people I’m from Long Island than explain the reality of growing up in an area notorious for its status as a playground for the rich and famous with sky-high real estate prices and club entry fees in the hundreds of dollars. 

I come from a working-class family that just so happens to be from the Hamptons. Myself, my mom, and her mom all grew up in Hampton Bays. My dad hails from the North Fork, where my grandpa and his father before him were farmers. We’re not from what socialites might call “good stock,” but rather blue-collar trades. In fact, my sister and I were the first in our family to graduate from college. 

My experience is one that I shared with many of my peers growing up. Sure, my high school had the rare rich kid, but for the most part we were a populus of working-class people. After all, the East End of Long Island does not have much white-collar industry. 

Trades like agriculture and fishing dominate the Hamptons for year-round locals. In addition to working at restaurants and retail shops, it was typical for high schoolers to get summer jobs at local farms or work for their parents’ plumbing business. My hometown is host to one of the largest commercial fishing ports in the state, second only to Montauk. And the trades — landscaping, construction, electric, and plumbing — cater to the influx of people that retreat to their Hamptons homes between Memorial Day and Labor Day. 

It’s no secret that the Hamptons swells in population during those coveted summer months. According to local newspaper The East Hampton Star, its namesake town alone may be home to around 35,000 year-round residents, but then between 120,000 and 175,000 during the summer, with holiday weekends seeing the higher end of that figure. 

I’m not proud to admit that I’ve held resentment for this group of people for pretty much my entire life. As a teenager working at a shoe store in Southampton, I witnessed women my mom’s age buying their 15-year-old daughters $600 shoes. Meanwhile, my own weekly paycheck couldn’t even cover the left foot of that pair and my single mom’s three jobs could just barely keep our family afloat. 

Here was a group of people who led markedly different lives to my own, with seemingly nothing in common aside from maybe a shared love for Cooper’s Beach and an appreciation for the free parking off Jobs Lane. And yet, we somehow found ourselves occupying the same physical location, at the same point in time. I never knew a relaxing summer. I instead knew intense stress brought on by busy work schedules and drastic changes in workplace pace. 

I knew, logically, that without this population of people (often not-so-affectionately referred to as “citiots” by locals), the Hamptons as I knew it wouldn’t exist. But it took me a long time to accept them, to understand and grasp that there can be a dichotomy of class in a single locale without resentment, and without one group turning on the other in an act of class warfare. Because as tired as I grew of catering to the ultra-wealthy, I can also understand why they migrate east each and every Memorial Day weekend. 

The Hamptons is a truly beautiful place, lush with green from late spring into early fall and rife with natural beauty. It’s not only home to sandy ocean and bay beaches, but also to forests and wildlife preserves, charged with the energy of a thriving independent ecosystem blissfully unaware of the value of the real estate it stands on. Deer frolic through the woodland, turtles slowly cross roads, and flocks of wild turkey are common sights. I took for granted the ability to go for a nature walk right outside of my front door or leisurely walk to the beach on a warm summer afternoon — something I deeply miss in my densely populated San Diego neighborhood. 

In time, I grew to understand that everyone deserves to experience this gentle beauty and the quietude that defines the East End of Long Island, whether they paid an exorbitant amount for a private estate south of the highway or they’re living paycheck to paycheck in a generational home they otherwise couldn’t afford. 

I may not have grown up in the Hamptons of other peoples’ imaginations, but I consider myself extremely lucky to have been immersed in that landscape during my formative years. 

As much as I loved the abundant greenery and humid summers that defined my young life, there came a time when the Hamptons no longer had anything to offer me. It felt as though I had exhausted my professional writing opportunities in the area, aside from maybe the romantic idea of sitting down to write a novel in a Montauk cottage overlooking Fort Pond Bay. My time had come to leave, so at 26 years old and in the final month of 2020 I drove out to the West Coast with my partner, crossing varied terrain in search of a different life. 

We all live with contradictions. As much as I miss the town where I grew up, I think putting 3,000 miles of distance between myself and the Hamptons was the best thing for me, allowing for a break from a lifestyle that operated in annual seasons that were contrasted by stillness and severity. 

Road trips are my partner and my favorite way to travel. Together, we’ve been to 32 states and counting. We have seen the Midwestern plains, coastal Oregon cliffs, dusty Texan highways, epic sky-high California Redwoods, and the vast Wyoming beauty. Yet, I still long to rise again to the northern cardinal’s morning song from the comfort of my childhood home.