Get to know Amagansett
Marilyn Monroe and Arthur Miller lived here. In the late 1950s, the most famous couple in America would escape to their small converted windmill home, where the famous playwright would write and the legendary actress would prepare for Some Like It Hot. Perhaps no other Long Island village or hamlet wears its mystique better than these 6.6 square miles in East Hampton dropped between the ultra-exclusive Maidstone Club and Montauk. After all, post-Marilyn and Miller, other residents of Amagansett have included the likes of Bill and Hillary Clinton, Paul McCartney, Jerry Seinfeld, and Billy Joel. Further Lane, which unwinds through East Hampton and continues east into Amagansett parallel to the beach, is one of the best addresses in the Hamptons, with locals able to recite by heart the sale prices of various mansions — since the owners are often famous.
History & Culture
The earliest settlers — who never could have imagined that their rustic adopted home would become world-renowned — were English and Dutch descendants who found the area inhabited by the Montaukett. The rich history of the hamlet, which was established in 1680, is safeguarded by the Amagansett Historical Association, the grounds of which includes structures from the 18th and 19th centuries. With special emphasis on the period from 1725 to 1925, the association houses carriages, furnishings, letters, and early photographs. Also located in Amagansett is the East Hampton Historical Society, which looks after seven historical buildings, including a farmhouse dating from 1680, a preserved shingled house from 1720 on Main Street, and the East Hampton Town Marine Museum.
Dine & Shop
Goods and services are plentiful on Montauk Highway/Main Street, which is abuzz with a few new restaurants that debuted for the 2019 season. Coche Comedor, from the same owners and executive chef as Nick and Tony’s in East Hampton, serves up tasty Mexican, while Morty’s Oyster Stand offers local and far-flung varieties, plus spicy poached shrimp and a $34 lobster roll. Sotto Sopra features Italian cuisine that’s a step above; the Northern Italian menu is courtesy of its Michelin-starred executive chef, Josh Salvi. Homeowners will become familiar with the Bayberry House & Garden Center, and sunbathers heading to Indian Wells Beach will want to stock up at Brent’s General Store and Amber Waves Farm.
Get to know Bridgehampton
Reaching deeply north into the South Fork and positioned between Water Mill to the west and Sagaponack to the east, Bridgehampton has a name that begs for even more geographical clarification. This one is easy: The bridge in Bridgehampton refers to a bridge built across Sagg Pond by Ezekiel Sandford in 1686. Bridgehampton is undeniably the essence of posh, and for many Hamptonites, the summer simply does not end until the occurrence of the Hamptons Classic, one of the largest outdoor horse shows in the country. Perhaps Bridgehampton is even better known for the $43.5 million property rented by Beyonce and Jay-Z — and for Madonna causing a stir when she was accused of buying a parcel for a “tree farm,” adjacent to her horse farm, that was widely viewed as a bid for privacy, not agriculture. Perhaps she commiserated with another Bridgehampton resident, fashion designer Isaac Mizrahi, who designed a leather handbag named for the hamlet.
History & Culture
Located in the town of Southampton, Bridgehampton was founded in 1640, but one of its most notable historical footnotes happened a century and half later, when a notorious criminal with a magnanimous streak and literary bent, the counterfeiter Stephen Burroughs, helped found the hamlet’s first library. A more complete story of Bridgehampton can be found at the Bridgehampton Museum, which contains such artifacts as 1,300 historical photographs, 300 historical books and Bibles, and collections of letters, ledgers, datebooks, textiles, and decorative arts. Bridgehampton also boasts the Children’s Museum of the East End, which attracts nearly 75,000 visitors annually, and the Dan Flavin Art Institute, a converted farmhouse that contains the late artist’s mesmerizing fluorescent works. And given the primacy of the Hamptons Classic, horse farms and other equestrian sites abound, from boarding and training at Billington Stables to elder care at Amaryllis Farm Equine Rescue.
Dine & Shop
Busy all year round, Bobby Van’s is that rare national chain restaurant (seven in New York, two in D.C.) that has become identified with the Hamptons. The menu has a few surprises, reaching beyond the standard steakhouse fare of steaks, chops, clams, and shrimp cocktail to offer such choices as Icelandic cod and a Spanish octopus salad. Meanwhile, Almond, a French-influenced bistro, is truly a Hamptons institution and a community builder, serving up artists’ and writers’ nights along with escargot and Le Grand Macaroni & Cheese with prosciutto and preserved summer truffles. And topping out the top three is Topping Rose House. One of the few luxury hotels in the Hamptons, the venue pulled off a big coup last year by enlisting no less than Jean-Georges Vongerichten to run its restaurant. Meanwhile, good shopping is happening on Main Street, where the usual suspects — J. Crew, Theory, Club Monaco — give way to more local boutiques.
Get to know East Hampton
When people refer to East Hampton, they likely mean East Hampton the village, as opposed to East Hampton the town, the latter of which contains East Hampton village as well as the villages and hamlets of Montauk, Northwest Harbor, Springs, Wainscott, Amagansett, and a part of Sag Harbor. (Note: Every village and hamlet in the Hamptons lies either in the town of East Hampton or in the town of Southampton, its neighbor to the west and south.) So, with that bit of geography and terminology in place, when people refer to East Hampton, they are also referring to a world of money, a place where the words privilege and exclusivity come up well short. Some of the sites in East Hampton are synonymous with ultra-elite society: The Maidstone, Georgica Pond, and the infamous Grey Gardens, all iconic, capture the village’s exaggerated prestige. But East Hampton is also a picturesque resort of natural beauty, and the quality of its white sand beaches is undeniable.
History & Culture
Puritan settlers, a famous witchcraft trial, and meticulous regulation are all part of an East Hampton legacy of do’s and don’ts. The size of homes and the number of beach parking passes are sharply limited. A hilarious assessment by the late “Little” Edie Bouvier Beale, the eccentric subject of the campy documentary Grey Gardens (1976), is well known for its quirky but deadly accuracy: “They can get you in East Hampton for wearing red shoes on a Thursday.” Established in 1891, the Maidstone Club is so picky about its membership that even George Plimpton and Diana Ross were denied membership (even though the latter’s billionaire husband was a member). The scenic lagoon of Georgica Pond played summer host to President Bill Clinton (at the home of Steven Spielberg, no less), and its residents have included Martha Stewart and Calvin Klein. If rigorous attention to maintaining the flavor of East Hampton is perhaps off-putting to visitors, locals reap the benefits of sky-high property values and its shingle-style architectural history.
Dine & Shop
Point one: Nick & Tony’s on Main Street is the East Hampton dining institution. For those not in the know, when The New York Times six years ago offered that the most coveted real estate in the Hamptons was a choice table in the eatery’s front room, the message was indisputable. 1770 House Restaurant, East Hampton Grill, and the Palm are also must-do’s on Main Street. For burgers, baked clams, steamers, and lobster rolls, a more casual gastronomic experience can be had on the pretty patio at Bostwick’s Chowder House. International brands are represented by Ralph Lauren (and Lauren’s daughter’s confectionery, Dylan’s Candy Bar), Lululemon, J. Crew, Vilebrequin, and Audemars Piguet (the watchmaker); some shops are open only for the season.
Get to know East Quogue
Livability and lifestyle are the watchwords of East Quogue, a hamlet of 11.5 square miles nestled in the town of Southampton between Quogue, Westhampton, and Hampton Bays. With its prime position on scenic Shinnecock Bay, the manta ray-shaped East Quogue isn’t flashy, pretentious, or as pricey as Quogue, but it is picturesque, with ample protected natural reserves and lovely white sand beaches backed by dunes. East Quogue is also convenient, with an adequate amount of restaurants, shops, and professional or other services — from lawyers, accountants, and dentists to home care and boat care — all located on (or right off) Montauk Highway, which serves as Main Street and snakes up the hamlet in a northeasterly direction past the inlets of the irregular coastline. (You can also get your hardware and fishing supplies here.) One of the best things about tiny East Quogue is that it’s not a day-tripper or glam destination, so residents can have it (almost) all to themselves.
History & Culture
East Quogue, known as Fourth Neck when it was settled in 1673, earned its current name in 1891. If you notice the last names Carter, Downs, Phillips, Jackson, Foster, Howell, Reeve, and Squires, these were the families that settled the hamlet in the 19th century. According to the East Quogue Historical Society, which houses a trove of information, some of the early settlers were woodcutters, in addition to the usual suspects — fishermen and farmers. In some ways, the hamlet is less of a resort destination today than it was in the 1920s and ’30s, when well-heeled hunting parties went off into the woods, when there were local baseball teams, and, with East Quogue lacking a bridge, when boats would ferry the holiday crowd to the beach. Today, the hamlet’s lifestyle is still centered around fishing, boating, swimming, and beachcombing, with cultural events pegged, for year-rounders, to the doings at the local elementary school.
Dine & Shop
For fine dining, the first name on people’s lips is the Stone Creek Inn. More than 20 years ago, Frenchman Christian Mir, a chef, and his wife, Elaine DiGiacomo, restored a historic home to offer prix fixe and a la carte dinners with menu items like chicken liver mousse, Provençal bouillabaisse, and, for Bistro Mondays, escargot, poulet a la Normandie, and profiteroles. On the coast, the sunsets from Dockers Waterside are so stunning that the place draws diners from nearby towns. The seafood menu includes oysters, littleneck clams, lobster mac ’n’ cheese, and cioppino. Plus, Dockers has a voted-best happy hour and does a mean Sunday brunch, from the hearty (short rib hash) to the decadent (challah French toast). For sushi on Montauk Highway, there’s Sakura House Inc., and for pizza, heros, soups, and breakfast sandwiches, head to East Quogue Pizza and Deli (delivery available). Shopping — that means flowers, kids clothing, cards, jewelry, and home décor — can be found up and down Montauk Highway and Jessup Avenue.
Get to know Hampton Bays
Tucked away in the town of Southampton, the hamlet of Hampton Bays is bordered on the west by Flanders and East Quogue (and several ample county parks), and on the east by Shinnecock Hills. As its name suggests, the remainder of its boundaries are watery: the Peconic River, as well as numerous inlets, waterways, coves, and bays. Its beauty owes in part to its fragility: It was the New England Hurricane of 1938 that carved up the hamlet in this peculiar way, leaving the Shinnecock Inlet in its wake. That long and variegated coast grants commercial and casual fisherman plenty of access, and Hampton Bays is a thriving fishing port, second in the state behind Montauk. In terms of living here, the hamlet’s real estate is modestly priced compared to the better-known villages and hamlets in the Hamptons, but home values are rising, and the enclave is widely considered a shrewd investment.
History & Culture
Hampton Bays has played catch-up to the other, more popular Hamptons. In the 18th century, in a much smaller version, it was the dubious “star” of a sprinkling of hamlets that together made up Good Ground. The 11 hamlets were combined in 1922 and given the name Hampton Bays to appeal to the summer tourism trade. As with many places in the Hamptons, geography dictates, or at least inspires, the culture. Because Hampton Bays is blessed with so many protected bodies of water, it’s a haven for watersports and boating enthusiasts — there’s windsurfing, paddleboarding, and sailing aplenty. And the hamlet’s spirit has a high-minded, crunchy flavor best represented by the Ecological Culture Initiative, a 501(c)(3) nonprofit that focuses on environmental stewardship, pedestrian-friendliness, eco-tourism, historical preservation, and other efforts that connect to the area’s original Good Ground moniker. The organization’s concurrent goal is to keep generic, suburban sprawl at bay (no pun intended).
Dine & Shop
The most popular eateries are dotted along Montauk Highway, which runs east to west. Villa Paul, housed in a historic building, is beloved for its Italian menu; try the homemade ravioli with spinach and meat, or the veal Caprina with mozzarella and prosciutto in white wine sauce with capers. Then there’s 1 North, a classic steakhouse featuring surf-n-turf sliders and a 24-ounce porterhouse. And Cowfish boasts a gorgeous setting, Sunday brunch (French toast with three types of berries), sushi (try the Tumbleweed: spicy lobster and avocado), and Block Island swordfish for lunch. Also on Montauk Highway is the Hampton Bays Shopping Center (clothing), anchored by Macy’s. On the cooler side of the spectrum is the Hampton Music and Arts Shop, a full-service music store carrying new and vintage instruments and sheet music; the folks will also service your instrument.
Get to know Montauk
Located at the very tip of the South Fork of Long Island, the nearly 20 square miles of Montauk represent the easternmost spot in New York state. As such, Montauk feels like the end of the earth. It’s a place of enviable natural beauty, including six state parks. With a narrower range of temperature variation than similarly situated towns, it experiences comparatively warm winters, and its recorded summer averages don’t crack the 80-degree mark. Praised for its beaches, which rank among the best in the Hamptons, the hamlet has been home to such famous denizens as Andy Warhol, musician Rufus Wainwright, and Pulitzer Prize-winning playwright Edward Albee. It’s an exclusive place, but with a vibe that’s more casual and closer to nature than the more westerly Hamptons. And in terms of scenic appeal, Montauk’s dunes and sunsets give it the biggest wow factor of all the towns of East Hampton.
History & Culture
George Washington, Amistad — and something called Leisurama. Historically speaking, Montauk has a lot of texture and pedigree, making its mark in each century of the nation’s history. Montauk Point Light, which stands as a symbol of that pedigree, was approved for construction in 1792 under President George Washington; as such, it was the first public works structure built by the new U.S. government (visitors welcome). Nearly 50 years later, slaves who had taken over the Spanish ship La Amistad briefly disembarked near Montauk Point. And in the 1960s, a slew of prefab homes branded Leisurama were plunked down in Montauk to represent the typical American house. These days, people come to Montauk for the same reasons they did midcentury: to kick off their shoes, take to the trails over the grassy dunes, fish either onshore or offshore, and head out on the water on a sailing charter or sunset cruise.
Dine & Shop
Montauk is synonymous with fishing and sportfishing, and you would be smart to come here to savor the fruits of those labors that end up on your plate. Menu favorites include the local fluke and all manner of tuna poke and tartare (Crow’s Nest features both fish, as well as a Mediterranean-infused menu). Proximity to the coast of Maine means that lobster platters and lobster rolls are ubiquitous, from Duryea’s Lobster Deck and Red Hook Lobster Pound to a place that’s literally called The Lobster Roll Restaurant. At Bird on the Roof, you can shop and eat — the place is as popular for its beachwear as it is for its pancakes. Gosman’s Dock is another excellent place to mix dining and shopping: Have a waterside meal or frozen drink at Gosman’s Seafood Restaurant, Gosman’s Clam Bar, or Gosman’s Topside, then bust out your wallet at Homeport for gifts, accessories, and furniture.
Get to know North Sea
So named because of its prime location on the northern coast of Long Island’s South Fork, North Sea is a quiet hamlet in the town of Southampton. It boasts lots of waterfront on Little Peconic Bay and enjoys the cachet of being convenient to Southampton Village, Water Mill, and the Parrish Art Museum. The scene is rural and relaxed, with adorable dining options like the Coast Grill (edamame pot stickers, shrimp curry), North Sea Tavern (oysters and burgers), and BOA Thai. Noyack Road, which brushes North Sea Harbor before it unwinds parallel to the north coast, is the main artery.
Get to know Quogue
Surfers, literary folks, lovers of historic homes, and seekers of peace and quiet will find much to enjoy among the endless dunes and tall grasses of Quogue. There are fewer than 1,000 residents holed up in the 5 square miles of this high-status Southampton village. Locals cherish the legacy of Quogue’s literary cache, which includes midcentury legend Arthur Laurents, who wrote the books for the musicals West Side Story and Gypsy as well the screenplays for The Way We Were and The Turning Point. If it’s the time of life when you want to take a notepad to the dunes to pen the Great American Novel after you strip off your wetsuit, quiet Quogue just might be the perfect place.
History & Culture
Quogue has a long, sleepy history, dating from its 1659 purchase from the Montauk tribe. Coastal farmlands eventually gave way to a resort atmosphere, when shingle-style homes were erected by prominent families. Nearly 250 structures, built over the past several centuries, helped the Quogue Historic District land a spot on the National Register of Historic Places in 2016. Excitement comes in the form of tasty waves and nature pursuits: Though the East End of Long Island isn’t as identified with hanging ten as, say, the North Shore of Oahu, Quogue homeowners know that local and visiting surfers alike enthuse over one of the world’s best right-hand breaks. Though Quogue has been referred to as the un-Hamptons, it’s still a pretty exclusive place; it can take years to break in to the family-friendly Surf Club. The bald eagles, falcons, foxes, and owls of the Quogue Wildlife Preserve are less discerning; the 7 miles of trails are open 365 days a year.
Dine & Shop
Membership is also tight at the Quogue Beach Club, but there’s always the refuge of the gorgeous and comfy Quogue Club at Hallock House, the 5-year-old inn designed by the beloved Alexa Hampton. With a wine list courtesy of sommelier Joseph Reinis and a farm-fresh menu by the inn’s founding executive chef, Matt Birnstill, Quogue residents may want to look into a membership after an overnight and dinner (dining is available to members and hotel guests). Far more casual is Beth’s Café, Quogue’s version of the country-cute spot that’s an essential go-to for any Hamptons town. Open for breakfast and lunch, this is the place to get your gluten-free pancakes or huevos rancheros on, or to wash down your crab cake sandwich with a Peanut Stallion smoothie. Given Quogue’s small size, locals spill over into East Quogue and Westhampton Beach to eat and browse, though the Quogue Shop is the closest resource for local gifts, menswear, totes, beach art, and even dog collars.
Get to know Remsenburg
Shaped like an oven mitt extending into the waters off Long Island’s southern shoreline, Remsenberg, though set within the town of Southampton, has a lack of commercial glitz in a very un-Hamptons-like way. But with regard to real estate and exclusivity, it certainly belongs, as the hamlet is a magnet for theater folk, writers, and media figures who don’t have any desire to be in the center of the action but who appreciate country roads lined with historic homes. Residents have included writer P.G. Wodehouse (whose gravesite is found at Remsenburg Community Presbyterian Church) and Guys and Dolls composer Frank Loesser. Set due west of Westhampton, Remsenberg is reachable and crossed by the parallel arteries of Montauk Highway and South Country Road. Though its boundary with Speonk is indistinct, Remsenburg is the name given to the southern coastal area, with the former to the north; both names are used for Remsenburg-Speonk Elementary School.
Culture & Commerce
Residents enjoy Remsenburg’s no-stoplight culture and its lack of a business hub. Yet local pride is in evidence, as represented by the Remsenburg Association, a nonprofit devoted to maintaining the rural character of the hamlet — and discouraging development. The Remsenburg Academy, formerly a boys school dating from 1885, is the venue for ArtRemsenburg, a series of cultural events focusing on painting, photography, sculpture, and mixed media. Remsenburg Marina, on the hamlet’s west coast across the bay from Eastport, offers dockage, boat sales, and repairs.
Get to know Sag Harbor
Given its historical significance and unique position — it is located in both East Hampton and Southampton — Sag Harbor captures the soul and spirit of the Hamptons. Sag Harbor’s central business district (the whole of which earned a spot on the National Register of Historic Places) was so key to the whaling industry of the late 18th and 19th centuries that it scored a mention in Moby Dick. Thus the village became a magnet for merchants and entrepreneurs — and culture. A perfect place for the creative class centuries before the term existed, Sag Harbor has enjoyed a bustling commercial and artistic atmosphere since its founding. Such an environment has resulted in a year-round lifestyle. Between that and its irregular coastline, which allows many properties to boast water views, Sag Harbor (which also features the calm waters of family-friendly Havens Beach) is one of the most desirable addresses in the Hamptons.
History & Culture
Settled in the early 1700s, Sag Harbor’s historical bona fides are many. It served as a stage for the American Revolutionary War, with one of its hills becoming a battleground that saw British casualties and the capture of 90 British soldiers. Long Island’s first custom house was built in Sag Harbor, and the harbor itself played a role in the War of 1812. And so on. As the first port of entry of the U.S., Sag Harbor emerged as a hotbed of social vitality and thriving interaction where various kinds of people — soldiers, seamen, merchants, and artistic types — freely mixed. John Steinbeck was perhaps the village’s most famous literary resident of the 20th century; novelist E.L. Doctorow (Ragtime) and Pulitzer Prize-winning playwright Lanford Wilson also lived here. Sag Harbor’s well-respected nonprofit Bay Street Theater, founded in 1991, continues to nurture the town’s arts-and-letters reputation, as do the readings at Canio’s Books, which has been around since 1980.
Dine & Shop
No two ways about it: Sag Harbor has a thriving Main Street, and several dining venues come up again and again among the locals. Wölffer Kitchen bills itself and its sibling in Amagansett as “the first winery-owned restaurants on the East End,” and this spot has won devotees for its seasonal cuisine, community vibe, and selection of wines, ciders, and spirits. Page at 63 Main prides itself on local oysters and its sautéed veal piccata, as well as its more virtuous vegan vegetable grain bowl. BLT chef Laurent Tourondel has the low-key LT Burger, and the Neapolitan pies at the year-old Sag Pizza have been greeted with open arms. With Sag Harbor known for charm and taste, it’s small wonder that Main Street has at least two homewares shops that win raves: Fishers Home Furnishings and In Home.
Get to know Sagaponack
One of the poshest villages in the Hamptons, Sagaponack is situated in the town of Southampton between Bridgehampton and Wainscott. The tiny, roughly triangular land mass checks in at only 4.7 square miles, yet it possesses some of the most valuable real estate in the nation; indeed, its ZIP Code routinely ranks as the costliest in America, so it’s not the place to look for a bargain. The roster of boldfaced names of current and former residents reads like the guest list of the country’s most exalted dinner party: Caroline Kennedy, Lloyd Blankfein, Truman Capote, Billy Joel, Kurt Vonnegut, Jimmy Fallon, cartoonist Charles Addams, actor Roy Scheider. Sagaponack’s Daniels Lane, which runs parallel to the coast (and Sagg Main Beach and Gibson Beach) just might be the priciest street in America. Sagaponack is indelibly connected, somewhat infamously, with billionaire Ira Rennert, who scandalized locals when he built arguably the biggest home in America; the main house alone (and there are other buildings) measures 66,000 square feet.
History & Culture
Sagaponack’s earliest settlers in the mid-17th century were potato farmers, and some of the estates of today’s billionaires were constructed on former potato farms. The Sagaponack Historic District, which nabbed a spot on the National Register of Historic Places, is a source of local pride — and participation. Fully 131 buildings and sites uphold the standard; they include the post office, 17th-century homes, 18th- century residences in the Federal and Greek Revival styles, plus bungalows and examples of the boxy, anti-Victorian Foursquare style that appeared after the turn of the 20th century. Most contributing buildings on the Historic District’s inventory be found on or near Main Street; for example, Kurt Vonnegut owned the home at 620 Main, which was built around 1740.
Dine & Shop
Despite its coveted real estate, Sagaponack never really let go of its rural character. As in other Hamptons villages and hamlets, Montauk Highway represents the main commercial thoroughfare, though this stretch is sedate compared to the action in Sag Harbor, East Hampton, and Bridgehampton. Most of what you need can be found here and on Main Street, which runs perpendicular to Montauk Highway. Loaves & Fishes does prepared food well — blue fish salad, brownie pudding, along with shrimp, scallop, and feta stew. South of Loaves & Fishes is Pike Farms and the Sagaponack farmers market (cauliflower, beets, snap beans, berries). And Wölffer Estate Vineyard (entrance on Sagg Road) boasts several award-winning labels.
Get to know Southampton
The elite village of Southampton shares its name with the town of Southampton, which also encompasses Quogue, Sagaponack, North Haven, and other tony villages, and more than a dozen posh hamlets, including Westhampton, Water Mill, Bridgehampton, and North Sea. (Hamptons terminology: Villages are incorporated; hamlets are not. Every village and hamlet in the Hamptons lies either in the town of Southampton or in the town of East Hampton, its neighbor to the east and north. That ends the geography lesson.) What Southampton village offers is a lesson on where the action is on Long Island’s southern fork. It is also the most developed and densely populated spot, as well as the most diverse. Therefore, Southampton is the most cosmopolitan place to buy a home in the Hamptons, and the village is arguably connected to the most illustrious names, including Ford, Vanderbilt, and Du Pont.
History & Culture
Named for an English earl and settled in 1640, Southampton takes pride in its long-recorded history. Accounts suggest that the early settlers enjoyed an amicable relationship with the Shinnecock Native Americans, who helped the Europeans settle. By the early 20th century, Southampton established itself as a premier summer resort and became a magnet for the superrich, über-powerful, and supremely successful, and the village boasts some of the most architecturally and historically significant (as well as the most expensive) estates in the country. Boldfaced names who have called the village home include Calvin Klein, Tory Burch, Ian Schrager, Brooke Shields, author Tom Wolfe, and legendary modern artist Roy Lichtenstein. Those culturally pedigreed names signal Southampton’s thriving cultural scene. Galleries abound, and the Southampton Cultural Center is a hub of visual and performing arts (including the Center Stage Theater), as well as educational opportunities.
Dine & Shop
Southampton has a bustling Main Street for dining and retail therapy, with the Hamptons outpost of the chic Sant Ambroeus (its other elevated locales include Soho, the West Village, and Palm Beach), sending locals into rapturous praise for the crudo and the spaghetti alla chitarra. Snacking options are plentiful: Stop calorie-counting at the Village Gourmet Cheese Shoppe or the Fudge Company, and stock up on the toothsome craft creations from Tate’s Bake Shop (everything from chocolate chip pies to gluten-free bars). Back at home, those massive estates need lots of wall space to fill, so fortunately there’s the Tripoli Gallery and Arthur T. Kalaher Fine Art right in town, as well as the Mark Humphrey Gallery, which has exhibited such artists as Lichtenstein, Alex Katz, Donald Baechler, Helen Frankenthaler, and Ross Bleckner (the gallery is also your best bet for custom framing). And since this is one of the most Hamptons-ish Hamptons, yes, there is a J. Crew on Main Street.
Get to know Water Mill
Located in the town of Southampton and encircled by such well-known Hamptons names as Sagaponack, Bridgehampton, and the Southampton village, Water Mill oozes prestige and star power — in its low-key way. Its 12 square miles contain some of the costliest real estate in the country; Jennifer Lopez owns an estate here, and Richard Gere is a famous former resident. Geographically, Water Mill runs along a bit of Long Island’s southern shore (with some of the most sought-after homes on Flying Point Beach), encircles Mecox Bay (with numerous watery fingers reaching into the hamlet in all directions), and meanders nearly to the North Shore.
History & Culture
An actual water mill was the hamlet’s raison d’être: The original 40 acres were designated for the mill in 1644. The two-story shingle-style water mill (purportedly the state’s first) was in operation for three centuries, and now serves as a museum (and selfie magnet). Water Mill is a scenic place where the land and the paintbrush have long coexisted. The hamlet boasts an impressive artistic pedigree, with the 34,400-square-foot Parrish Art Museum attesting to the area’s identity as a haven for painters. More than a century old, the museum has commanded this Herzog & de Meuron-designed facility since 2012. It contains more than 3,000 pieces, including a peerless collection of works by the American Impressionist William Merritt Chase (1849-1916). A more eclectic space is the Water Mill Center, which is devoted to collaborations between visual and performing artists, scientists, and anyone who wants to learn and explore. The venue offers meditation, tours, a library, and peaceful gardens.
Dine & Shop
A stone’s throw away from the Parrish Art Museum is the family-owned Duck Walk Vineyards, with 30 acres of sauvignon blanc grapevines; and Hank’s Pumpkintown, which offers apple picking and pumpkin doughnuts. Dining go-tos include Calissa, featuring a Greek-influenced menu of mezze, grilled octopus, and branzino; and Bistro Ete, with its French coastal cuisine capped off by Foie Gras Fridays. Suki Zuki, serving sushi and robata grill dishes, is a hot spot. For coffee, quick bites, and takeout, locals and visitors on their way to the beach hit the Deli at Water Mill. And the Hampton Coffee Co., which features a coffee of the month, is particularly eco- and community-minded: In addition to offering beloved muffins and artisanal, small-batch Arabica coffee, this little family-owned business uses biodegradable cups and straws, ships with UPS Carbon Neutral, and employs (and will demonstrate) solar panels.
Get to know Westhampton
Thanks to the charming vagaries of Hamptons nomenclature, the hamlet of Westhampton is located within the town of Southampton. To many, Westhampton is regarded as the start of the Hamptons — it’s less buzzy and more family-friendly. And because Westhampton is not found in the center of the tony Hamptons, its real estate tends to be somewhat more affordable than the villages and hamlets due east. Cradling the village of Westhampton Beach and the hamlet of Quiogue to its south, Westhampton is large and irregularly shaped, like a couple of almost-square shapes stacked asymmetrically; the hamlet stretches from Sunrise Highway/Route 27 on its northern boundary to the waterfront in the south. In terms of its commercial profile, Westhampton is clustered in the Greater Westhampton Chamber of Commerce along with Westhampton Beach, Quogue, Quiogue, and several other villages.
History & Culture
Originally called Ketchaponack (“place where large roots grow”), Westhampton and parts of Westhampton Beach were extracted from the Shinnecock Indian Tribe for little more than 70 British pounds and awarded to Southampton Town in 1666 in a deal known as the Quogue Purchase. Three centuries later, Westhampton played an unexpected role in Cold War history, as its woods hid 56 nuclear-tipped missiles in the 1950s — the last line of defense against any potential Soviet attack. The missile base was decommissioned in 1964. Today’s excitement is more traditionally suburban, with tons of opportunities to improve one’s serve. The Eastside Tennis Club on Montauk Highway has a dozen private, lighted courts, while across the village line, the Westhampton Beach Tennis & Sport Club offers 28 more courts. The smaller Aspatuck Tennis Club has nine.
Dine & Shop
Most dining and commerce can be found along Montauk Highway. Casa Basso counts as destination dining for the whole family, as it features a miniature castle as well as primo straccia tella soup for two, veal piccata limone, and farfalle bellavista. Nearby, Jerri’s Cakery & Confections specializes in a complete cake inside a single-serve, 8-ounce Mason jar. Buoy One, one of the Hamptons’ top seafood names (other locations are in Riverhead and East Hampton), is represented here: The New England-style menu includes oyster or shrimp po’boys, fish ’n’ chips baskets (clams, calamari, bay scallops), coconut voodoo chicken (roasted red pepper sweet chili sauce, mashed potatoes, and broccoli), and almond-crusted flounder. Westhampton’s Farmers Market Farm Stand is especially well-equipped, with locally grown veggies and fruits, quiches, muffins, seafood, and even raw honey from local hives. The best shopping options convenient to Westhampton include Riverhead and Main Street in Westhampton Beach, though the village boasts the unique Certain Books, which specializes in antiquarian tomes, maps, and historical manuscripts.
Get to know Westhampton Beach
Shaped like an upside-down cork that’s been split at the fat end — that is, the wide coastal end — tiny, casual Westhampton Beach has lots of shoreline, and a population of around 2,000. Incorporated as a village in 1928, it’s located in the town of Southampton, with Westhampton to the east and Quiogue to the west. Of course, as its name would indicate, its key draws are the spectacular white strands along Dune Road. Cupsogue Beach County Park wins raves for its beauty, lack of crowds, and soft sands, while people looking for a non-party scene favor Pike’s Beach for the same reasons — and find the lack of vendors a blessing. Still others are attached to Roger’s Beach, noting its friendly lifeguard community, wooden benches, and snack bar. The prospective homeowner can do some serious bodysurfing from the prized sands off Dune Road and then find a noticeably democratic array of housing, from gorgeously imposing estates to condos to modest beach cottages.
History & Culture
The best place to learn about the history of the village is the Westhampton Beach Historical Society, which also serves the communities of Westhampton, Westhampton Dunes, Remsenburg, Quiogue, and Eastport. More than a single building, the campus consists of the historic Tuthill House Museum, the Foster-Meeker Heritage Center, the Meeker Carriage House and Privy, and the Thurston Raynor Milk House. The Foster-Meeker House, which is being restored, dates from 1735 and is considered the oldest house in Westhampton Beach. The event that most impacted the village’s story happened less than 100 years ago, when the Great New England Hurricane of 1938 destroyed homes, submerged the downtown, and carved the Shinnecock Inlet. On a happier note, the cultural venue that put Westhampton on the map in a different way is the Westhampton Beach Performing Arts Center, which dates from 1932 and hosts musical performers of all genres as well as standup comedy. The village also boasts the indie Hampton Arts Cinema.
Dine & Shop
A cluster of eateries is located on and around Main Street between Mitchell Street and Beach Road. Included are such sources of comfort food as the Post Stop Café, with its pretty porch; Eckert’s Luncheonette, crowd-pleasing for its midcentury ambiance; and Beach Bakery Grand Café, which serves up a hearty breakfast and tasty pastries. Shock Ice Cream satisfies with its portions and is more inventive with flavors and presentations than it needs to be, since it has little competition in a laidback downtown. For sunsets and seafood, John Scott’s Surf Shack on Dune is the ticket. Like the dining scene, shopping options aren’t pretentious or particularly posh. But you’ll find a few jewelry stores, Impulse for men’s apparel, and on the distaff side, the Mint Clothing Boutique and the Lynn Stoller Collection, a consignment shop a stone’s throw from the local Corcoran office.