Unlocking The Secrets Of The Hamptons

Rex Chatterjee
5 min readJun 13, 2020

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The Hamptons have long been a place of mystery and wonder. With big-name celebrities and billionaire tycoons inhabiting jaw-droppingly large beachfront mansions, it’s no surprise that people from all over are curious about the area.

Now, in the age of the internet, there’s a lot one can find out about a place via Google. But, just like with other notable hangouts of the rich and famous (like St. Barths, Monaco, St. Tropez, and others), some of the best places to eat, shop, and more, are simply hidden from view (unless you’re a reader of Dune Road Lifestyle).

But now, I’m going to give you an honest look into the best places to eat, shop and stay when traveling to the Hamptons for the summer (particularly summer 2020).

So, What Is The Hamptons, Anyway?

The Hamptons are a series of towns comprising the South Fork region of Suffolk County. A map will help us explain:

A map showing the location of the Hamptons in relation to the North Fork and parts of Eastern Suffolk County, New York.
Credit: Google Maps (Annotation By Author)

The map above, which I’ve clipped from Google Maps, shows the eastern portion of Suffolk County, the easternmost county on Long Island, in New York.

At its eastern end, Suffolk County splits into two “forks,” aptly named the “North Fork” and the “South Fork,” and with Shelter Island sitting between them. The Hamptons area is located on the South Fork, comprising it in its entirety.

In terms of towns, the Hamptons stretches from Westhampton Beach at its westernmost point, to Montauk at its easternmost. In between, you have the various regions of East Quogue, Quogue, Hampton Bays, Southampton, Water Mill, Bridgehampton, Sagaponack, Sag Harbor, Wainscott, East Hampton, Amagansett, and Montauk. There are other smaller towns within the area as well, but these are the main areas of the Hamptons on which we’ll focus our attention.

Note: I should pause here to say that there are several media sites out there that cover places to visit “out east” (as the Hamptons are sometimes called). You’ll find coverage on Yelp, of course, and national sites like Travel & Leisure more broadly, and also more specific coverage on sites like Dan’s Papers and The Independent. However, if you’re looking for a true insider’s take, your best bet is to check out Dune Road Lifestyle.

And now, without further ado, let’s explore the hottest areas of The Hamptons:

Notable Hamptons Areas

Southampton / Water Mill

On the relatively western side of the Hamptons is where you’ll find the celeb-filled hotspots of Southampton and Water Mill, the latter being mostly houses with residents going into the former for shopping, dining, and the like.

If you’re a fan of reality TV, you’ll have noticed that the cast of Bravo’s Summer House tends to frequent Southampton Social Club on the regular. However, if you’re in the area and looking to pop some bottles, you may want to look to the more undercover Hedge Club for a more celebrity-laden experience.

Of course, the main party scene in the area is most certainly the Hamptons celebrity house parties. And I use the word “celebrity” loosely, as there’s plenty of high-spending Hamptons renters who throw massive summer parties for themselves, their friends, and of course, celebrities and models at some of the mega estates located in Southampton and Water Mill.

Now, some celebrities value their privacy, and may shy away from the more known areas of Southampton, opting instead for areas like North Sea. Such can be said for Rihanna, who, this summer (2020), has rented a house there for $415,000.00 / month.

If you’re in the area, though, the place you really need to go to see and be seen is Bistro Eté in Water Mill.

Bridgehampton

Usually more restrained in its expression of luxury / celebrity culture, Bridgehampton played home to one of the “scene-iest” parties the Hamptons has ever seen when, in 2017, REVOLVE hosted a party at an epic Bridgehampton mansion.

Photo by Vicko Mozara on Unsplash

Nevertheless, I’d be remiss if I didn’t mention that a stay at Topping Rose House is a must for anyone looking to better understand the understated luxury that’s become the signature of Bridgehampton.

East Hampton

East Hampton, at least partly, is the Hamptons version of Hollywood in terms of its casual celebrity run-ins. For example, if you were at Serafina over Easter weekend, you may have been standing next in line from none other than Hugh Jackman. Or, you might be out at a book shop and see Alec Baldwin out browsing books.

But, the thing you’re missing out on, if you don’t already know, is Highway Restaurant. Despite its relatively ordinary name, the place is anything but. It’s one of the best restaurants I’ve ever eaten at, and I don’t think I’ve ever had a bad experience there.

Montauk

If there’s one place in the Hamptons you’ve heard of lately, it’s the Surf Lodge. A local hotspot for celebrities and influencers alike, the Lodge has been making a huge impact in raising the profile of the Hamptons globally over recent years.

Photo by Alexis Balinoff on Unsplash

However, a lot of more low-key celebrities and other notables, such as Ralph Lauren and Robert DeNiro, call Montauk their second home as well. It’s definitely a mix, with some of the most Insta-ready celeb moments, and some amazing homes with celeb owners that just go there for the beach.

If you’re looking for an experience that’s somewhere in the middle — Insta-worthy and glamorous but lower-key and chill — you’ve got to check out The Montauk Beach House.

Now, there’s a lot more secret spots and inside knowledge on the Hamptons to tell you, but it’s far too much to put in one article. On Dune Road Lifestyle and their Summer 2020 Hamptons Guide, however, you’ll find a lot of it. If you’re interested in more essential Hamptons info, head over to the site and read up.

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