Which Hamptons town should you visit?

East End towns tend to be grouped together when people say that they’re “going out to ‘the Hamptons.’” But each town and hamlet is unique, and has its own personality and individual characteristics.

There are two main townships on the East End: Southampton and East Hampton. Within each of these larger municipalities there are “villages” (the larger towns) and “hamlets” (the smaller neighborhoods). Westhampton Beach and Bridgehampton, for example, are both in Southampton’s jurisdiction, while Montauk and Amagansett are in East Hampton.

If you’ve never been to the Hamptons before, it can be difficult to choose where to stay or spend your time. Here, we break down each of the villages and nearby communities’ vibes to make deciding where to go just a bit easier.

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West of the Canal

Including Westhampton, Quogue, East Quogue, and Hampton Bays

Westhampton Beach and the other oceanside towns to the west of the Shinnecock Canal are not considered in “the Hamptons” (even though some of them have “Hampton” in their names and Westhampton is technically part of Southampton township—go figure!).

While Hamptons purists might sniff at these not-quite-Hamptons towns, come summertime, you’ll find the same pristine ocean beaches and plenty of vacationers. However, there’s less of a feeling that you’ve escaped the hustle and bustle of the everyday Long Island ’burbs. On the plus side, there’s a more robust year-round community (and more amenities) and you’re closer to the city (read: less summer traffic to contend with). Plus, you’ll likely pay less for rentals and hotels than you will in the Hamptons proper. In general, bars and restaurants are a bit more laid back as well.

Southampton

Including Water Mill and North Sea

Southampton is typically where realtors and locals define the start of the East End—and thus, this is where everything (gas, groceries, hotels, vacation rentals) starts to get a bit pricier. It’s also where traffic slows to a crawl come the high season.

The town of Southampton is the largest of the villages on the East End in both population and the size of its downtown. Unlike many of the other East End villages, Southampton’s downtown is not centered on Route 27, but farther south on Main Street and Jobs Lane, where you’ll find high-end boutiques, restaurants, and a handful of galleries. Of all the Hampton villages, Southampton feels the most like the “Hamptons” you see on television and glossy magazines.

The village of Watermill, named for its historic mill, which you can visit, has its own small downtown area along Route 27 with a few restaurants and a shopping center, but no amenities like a grocery store, pharmacy, or gas station.

To the north, North Sea is the westernmost of the sleepier hamlets that hug the Peconic bays and Noyak Bay; there is no town center proper, but there are a variety of businesses along Noyak and North Sea Roads.

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Sag Harbor

Including Noyack and North Haven

Sag Harbor, an old whaling port, is the only large village on the northern side of the South Fork. To add to the confusion of villages versus townships, Sag Harbor is an incorporated village that sits in both Southampton and East Hampton. Perhaps because it’s farther from the ocean beaches, and therefore had less cachet in earlier decades, it has retained a quaint feeling.

All the East End towns have historic pasts, but the feeling of history is most palpable walking the streets of Sag Harbor. Filled with independently owned businesses rather than the outposts of major retailers that you’ll find in Southampton and East Hampton, the village feels authentic. The train does not come to Sag Harbor, but you can take a Jitney bus to the center of the village, and the area’s downtown is very walkable, with all the conveniences (grocery store, liquor store, pharmacy) you might need. There are options for those who need a cultural fix at places like the Whaling Museum or the Bay Street Theater.

Noyack sits to the northwest of Sag Harbor, and North Haven sits on the peninsula due north. Neither hamlet has a proper village or main street. Both are quiet and lushly green.

Bridgehampton

Including Sagaponack and Wainscott

Bridgehampton is the largest of the villages between Southampton and East Hampton. With its main drag along Route 27, Bridgehampton has a mix of restaurants and shops. Two rainy-day kid destinations, the Children’s Museum of the East End and the Southfork Natural History Museum & Nature Center, are a couple miles north of town. Even on an August weekend, downtown Bridgehampton feels more low-key than East Hampton or Southampton (though the lines at the area’s gourmet grocery store, Citarella, are as crazy here as anywhere else).

The stretch between Bridgehampton and East Hampton, which includes the hamlets of Sagaponack and Wainscott, is perfect for those who want to be near the ocean, but away from the hustle and bustle—though there are no hotels, and rental homes come with a steep price tag. The south-of-the highway hamlet of Sagaponack has just a post office and a general store (now operated as a high-end deli by Pierre’s of Bridgehampton). Wainscott has no walkable village area—just a grouping of businesses along Route 27.

East Hampton

Including Springs and Northwest Harbor

East Hampton is physically at the heart of the East End, approximately equidistant to both Montauk and Southampton—and its place in the spectrum of Hamptons-ness is about center, as well—not uptight, but not totally laid back either. Both the train and Jitney stop right in East Hampton, and you can walk to local hotels, as well as the shops, restaurants, and movie theater. Ocean beaches are not far from the village. East Hampton has a relatively large concentration of cultural attractions in its downtown, including Guild Hall, the local performing and visual arts center, and five small museums that are operated by the East Hampton Historical Society.

Northwest Woods lies to the northwest of East Hampton, and Springs to the northeast. The Northwest Woods has no downtown area or businesses, and as its name suggests is heavily wooded. You can camp and hike in Cedar Point County Park. Springs has long been known as an artist’s haven, home to Jackson Pollock and Willem de Kooning in their heydays (you can visit Pollock’s home and studio in the summer, but make a reservation). Today it’s still home to artists like Cindy Sherman and Ross Bleckner. These hamlets are also where many of the year-round residents of East Hampton reside and where rental home prices are lower. Springs has a small village center near Ashawagh Hall and the Springs General Store.

Amagansett

Including Napeague

Heading east from East Hampton, the village of Amagansett feels a bit removed from the hum of the larger villages to the west. The vibe is also more bohemian—instead of Ralph Lauren, you’ll find an Ulla Johnson clothing boutique (opening this summer). Similar in size to Bridgehampton, Amagansett’s downtown area is centered on Route 27 with a large village green surrounded by shops just south of the highway. The distance from the town to beach is shorter in this town, making Amagansett a great choice for someone hoping to spend a weekend without a car. However, it has fewer places to dine out in the evenings than the other East End villages.

Like many other hamlets, Napegue, the narrow stretch of land between Amagansett and Montauk, does not have a main street—just a few businesses along 27, including two iconic lunch stops, Clam Bar and Lunch. Here is where the stately trees and privet hedges give way to scrub pine and open sky. It’s also home to several oceanside condominium developments.

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Montauk

Located on the easternmost end of Long Island, Montauk is sometimes called “the End,” and if you venture out to the lighthouse you’ll understand why: The vistas from the point are nothing but sea. Montauk is considered the preferred destination for surfers and sport fisherman. In recent years Montauk has also gotten a reputation for being the life of the party in the Hamptons—with dozens of new hotels and restaurants that cater to the chic city set.

Montauk is also arguably the least fancy spot on the South Fork, with putt-putt mini golf, a drive-in burger joint, and competing pancake houses. Hotels are cheaper here—and plentiful—and many are within walking distance of both the ocean and the train and bus stations. However, Montauk is spread out over many miles (much of it is state and county parkland), so if you want to see the historic lighthouse, Hither Hills State Park, and the marina to the north, you’ll still want a car.

North Fork

Including Riverhead and Shelter Island

While the North Fork isn’t really considered a part of the Hamptons, we’re including it here because it’s still part of the East End (and it’s going to show up in your vacation rentals search). A short ferry ride north of Sag Harbor, you’ll find Shelter Island. Hop on a second ferry on the north side of the island and you’ll reach the bustling town of Greenport.

Despite what you may have heard about the wild party scene at Sunset Beach Hotel, Shelter Island is a sleepy place with little in the way of nightlife and a lot in the way of old-school charm and nature. Greenport, on the other hand, becomes more and more Hamptons-like with each passing year, as new shops and restaurants fill the downtown storefronts.

While Greenport has become more of a destination, it and the rest of the North Fork are still more rural than the Hamptons. And what the North Fork lacks in oceanfront, it makes up for in greater affordability, vineyards, and the feeling that you’re out in the “country” (not just New York City transplanted to the beach). Prices are lower than on the South Fork, and because the North Fork is a bit less of a tourist attraction than its neighbors to the south, there are more locals. Plus, most restaurants and establishments are open year-round.