The Hamptons

Discovering the Hamptons

The Hamptons begin where the suburbs end. Somewhere east of Riverhead, where the Long Island Expressway finally runs out of lanes and Route 27 narrows to a two-lane road, the landscape shifts. Strip malls give way to potato fields. Subdivisions yield to hedgerows so tall they form green walls along the roadside, concealing estates that have sheltered New York’s wealthiest families for generations. The light changes too — softening, brightening, taking on a quality that painters have chased to this stretch of coast since the 1800s. By the time you reach Southampton, you understand why people endure the Friday afternoon traffic: the South Fork of Long Island is genuinely, breathtakingly beautiful, and there is nothing else quite like it on the Eastern Seaboard.

The Hamptons are not one place but a string of villages and hamlets stretched along roughly 35 miles of Atlantic coastline — Westhampton Beach, Quogue, Hampton Bays, Southampton, Water Mill, Bridgehampton, Sagaponack, East Hampton, Amagansett, and finally Montauk at the very tip. Each has its own character, its own social identity, its own subtle hierarchy understood by summer residents and largely invisible to visitors. What they share is extraordinary: wide white-sand beaches backed by rolling dunes, rich agricultural land that still produces corn, potatoes, and pumpkins, a concentration of wealth that has shaped one of America’s most distinctive landscapes, and a natural beauty that persists despite — and sometimes because of — the money that has been poured into preserving it.

The story of the Hamptons as a summer destination begins in the mid-1800s, when artists from the Tile Club — a group of New York painters and architects — discovered the luminous coastal light and began spending summers in East Hampton. William Merritt Chase established his summer art school on the Shinnecock Hills in 1891, and the artistic colony drew attention from Manhattan’s social elite. By the early 1900s, wealthy New Yorkers were building grand summer estates along the dunes, establishing the social framework that still defines the Hamptons today. The roster of families who have summered here reads like a roll call of American power and influence — Fords, Bouviers, de Menils, Spielbergs, Seinfelds — and the blend of old money, new money, artistic ambition, and agricultural tradition creates a texture that no other American beach community quite matches.

But here is the thing about the Hamptons that gets lost in the celebrity gossip and real estate listings: the place is genuinely, deeply beautiful in ways that have nothing to do with money. The light at golden hour on Cooper’s Beach is extraordinary. The quiet back roads through Sagaponack, where farm fields run right to the edge of ocean bluffs, feel like a different century. A dozen oysters at a Sag Harbor waterfront bar, shucked from beds in the Peconic Bay you can see from your seat, is one of the great simple pleasures in American dining. The Hamptons reward visitors who look past the scene and engage with the landscape, the food, and the deep, layered history of a place that has been attracting people for very good reasons for a very long time.

The Beaches

The beaches are the foundation of everything. The Hamptons sit on the south shore of Long Island’s South Fork, facing the open Atlantic, and the result is a continuous stretch of wide, white-sand beach that ranks among the finest on the East Coast. The sand is fine and pale, the waves are consistent but rarely dangerous, and the dunes behind the beach create a natural buffer that makes you feel, even on a crowded July Saturday, like you have found your own corner of the coast.

Cooper’s Beach in Southampton has been rated the number one beach in America by multiple publications, and the accolade is earned. The sand is impossibly wide — 300 feet from the dune line to the water at low tide — and the beach stretches east in a gentle crescent that catches the light beautifully all afternoon. The parking lot fills early on summer weekends ($50 for non-resident parking, which is itself a statement about the Hamptons economy), but the beach itself absorbs crowds without ever feeling packed. Walk east for ten minutes from the main access point and you will find stretches where you can spread your towel without another person within throwing distance.

Main Beach in East Hampton matches Cooper’s for beauty and exceeds it for social energy. This is where the scene happens — the beautiful people in their carefully curated beach setups, the volleyball games, the lifeguard stands that have appeared in countless magazine photos. Behind the beach, the dunes are dramatic and well-protected. The village of East Hampton is a short walk north, making Main Beach the most convenient for combining beach time with lunch and shopping.

Sagg Main Beach in Sagaponack is the insider’s choice — less crowded, equally beautiful, with a wilder feel and fewer amenities. The potato fields of Sagaponack run almost to the edge of the bluffs above the beach, creating a juxtaposition of agriculture and ocean that encapsulates the Hamptons landscape. Ponquogue Beach in Hampton Bays offers the best value — lower parking fees, great waves, a functioning snack bar, and a less status-conscious atmosphere. For surfing, Ditch Plains in Montauk is the undisputed center of Long Island’s surf culture, with consistent breaks and a community of year-round surfers who have been riding these waves for decades.

Southampton — Old Guard Elegance

Southampton is the oldest English settlement in New York State, established in 1640, and its sense of history and permanence is evident in every hedgerow-lined lane. The village center is compact and walkable — Jobs Lane and Main Street form the core, lined with boutiques, galleries, and restaurants that cater to a clientele accustomed to quality. The architecture is a mix of colonial-era buildings, grand Gilded Age mansions, and tasteful contemporary storefronts that maintain the village’s visual coherence.

The Southampton Historical Museum occupies a complex of historic buildings including the 1648 Halsey House, one of the oldest English frame houses in New York. The Parrish Art Museum, now relocated to a stunning Herzog & de Meuron-designed building in nearby Water Mill, originated in Southampton and maintains deep connections to the community. Its permanent collection focuses on artists who worked on the East End — Fairfield Porter, William Merritt Chase, Dan Flavin — and the building itself, a long, barn-like structure with north-facing clerestory windows, is a masterwork of architecture that draws on the agricultural forms of the surrounding landscape.

The estate district of Southampton extends along Gin Lane and Meadow Lane, where some of the most expensive residential properties in the United States sit behind walls of privet hedge. You cannot see much from the road — the hedgerows are deliberately impenetrable — but the scale is visible in the driveways, the gates, and the sheer length of the property frontages. The Beach Road that connects Gin Lane to Cooper’s Beach passes through this district and offers a sense of the neighborhood’s character without intruding on anyone’s privacy.

East Hampton — Creative Energy

East Hampton has always been the more culturally dynamic of the two main Hamptons villages. Jackson Pollock and Lee Krasner lived and worked in Springs, just north of the village, and their studio (now a museum) is a pilgrimage site for art lovers. Willem de Kooning, Alfonso Ossorio, and a constellation of Abstract Expressionists followed, establishing an artistic legacy that continues today. The village has attracted writers (Kurt Vonnegut, E.L. Doctorow), filmmakers (Steven Spielberg, who has a large estate in the area), and musicians — and this creative history gives East Hampton a different energy than Southampton’s more purely social atmosphere.

The village itself is beautiful — a wide main street lined with elms, a 1680 windmill (the Hook Mill, one of the most photographed landmarks on the East End), and a cluster of excellent restaurants and shops that cater to a discerning audience. Guild Hall, the community’s cultural center since 1931, hosts exhibitions, theater productions, and lectures that draw major artistic talent throughout the summer season.

Dining in East Hampton reaches heights that rival Manhattan. Nick & Toni’s has been the power-dining destination for decades — the wood-oven-cooked Mediterranean dishes ($35-60 entrees) are excellent, but the real draw is the room, where on any given summer evening you might spot faces from the front pages of Variety and the Wall Street Journal. The 1770 House offers a more intimate experience — fine dining in a candlelit historic inn that feels like a private dinner party. For something more casual, the Golden Pear serves outstanding breakfast and lunch ($12-22), and Bostwick’s Chowder House delivers excellent fried clams and lobster rolls on a patio overlooking the train tracks.

Sag Harbor — The Whaling Village

Sag Harbor is the most genuinely charming town in the Hamptons, and the one that feels most like a real place rather than a stage set for wealth. Once one of the great whaling ports of the Atlantic — rivaling Nantucket and New Bedford in the early 1800s — Sag Harbor retains the architecture and character of its maritime heyday. The whaling captains’ homes along Main Street, with their widow’s walks and Greek Revival facades, are beautifully preserved and still occupied as private residences. The Sag Harbor Whaling & Historical Museum, housed in an 1845 Greek Revival mansion, tells the story of the town’s whaling era with harpoons, logbooks, scrimshaw, and paintings.

The village is the most walkable in the Hamptons. Main Street slopes gently down to the waterfront, passing the Bay Street Theater (an intimate venue that programs excellent summer stock), independent bookshops, galleries, and restaurants. The American Hotel, a historic inn with a mahogany bar and one of the finest wine lists in New York State, anchors the dining scene. Sen serves inventive Japanese cuisine in a sleek space. Page is the cocktail bar where locals and visitors mix over craft drinks and harbor views.

The waterfront itself is the village’s living room. The Long Wharf extends into Sag Harbor Cove, offering views of the bay, the breakwater, and the boats that range from modest sailboats to megayachts that appear during peak summer weekends. Watching the sunset from the Long Wharf, with the village rising behind you and the Peconic Bay stretching out to the North Fork, is one of the Hamptons’ most accessible and satisfying experiences — and it is completely free.

Bridgehampton & Sagaponack — Farm Country

Bridgehampton and Sagaponack represent the agricultural heart of the Hamptons, where the landscape is defined as much by fields as by estates. The rich glacial soil of the South Fork has supported farming for centuries, and the fields of corn, potatoes, and pumpkins that line the back roads are not decorative — they are working farms that supply the farm stands and restaurants that define the Hamptons food culture.

The farm stands are destinations in themselves. Round Swamp Farm in East Hampton is legendary — prepared foods, fresh produce, baked goods, flowers, and the kind of tomato that reminds you what tomatoes are supposed to taste like. Balsam Farms in Sagaponack operates a farm stand right at the field’s edge where you can see exactly where your vegetables grew. Amber Waves Farm offers CSA shares and a farm stand that embodies the Hamptons ideal of sustainable, local agriculture connected directly to the community.

Bridgehampton’s main street has evolved into a sophisticated dining and shopping corridor. Topping Rose House, a luxury hotel and restaurant in a restored 1842 house, represents the high end of Hamptons farm-to-table dining. Bobby Van’s Steakhouse is a longtime institution. The Bridgehampton Candy Kitchen, a diner that has been serving breakfast and lunch since the 1920s, is the kind of place where billionaires in flip-flops sit at the counter next to construction workers, and everyone orders the same pancakes.

Wine Country

The East End of Long Island has emerged as a legitimate wine region, with over 60 vineyards producing wines that earn serious critical attention. While most vineyards are concentrated on the North Fork across the Peconic Bay, the South Fork has its own notable producers, and wine tasting has become one of the Hamptons’ essential experiences.

Wolffer Estate Vineyard in Sagaponack is the South Fork’s showpiece — a 55-acre estate with a tasting room, a restaurant, and grounds that look like they were transported from Provence. Their rose is ubiquitous in the Hamptons during summer, and the Friday evening “Sunset Sessions” with live music on the lawn have become one of the season’s social anchors. Channing Daughters Winery, also in Bridgehampton, takes a more experimental approach — natural winemaking techniques, unusual grape varieties, and a low-key tasting room that attracts serious wine enthusiasts.

For a full wine day, cross to the North Fork via the Shelter Island ferry — a scenic journey in itself that takes you across the Peconic Bay and through Shelter Island’s quiet, forested landscape. The North Fork’s wine trail includes Bedell Cellars, Macari Vineyards, Kontokosta Winery, and dozens more, most with beautiful tasting rooms and views over the vineyards to the water. The round trip — South Fork to Shelter Island to North Fork and back — makes for one of the best day excursions on Long Island.

Practical Tips for Visiting

Getting There: The LIRR from Penn Station to Southampton takes about 2.5 hours and runs frequently in summer, with special express services on Friday evenings and Sunday afternoons. The Hampton Jitney is a comfortable coach bus from Manhattan’s East Side ($30-45 one way) with reserved seating, Wi-Fi, and a civilized atmosphere — it is genuinely pleasant travel. Driving takes 2 to 4 hours from Manhattan depending on traffic, and Friday afternoon traffic on the LIE and Route 27 is legendary — leave before noon or after 8 PM. The Hampton Luxury Liner is the upscale bus option with fewer stops and more legroom.

Getting Around: A car is the most practical way to explore the Hamptons, since the villages are spread over 35 miles and public transit between them is limited. The Suffolk Transit S92 bus runs along Route 27 but service is infrequent. Uber and Lyft work but summer surge pricing can be shocking — a 15-minute ride might cost $40-60 on a Saturday night. Biking is excellent within individual villages and on the back roads between them, though the distances (Southampton to East Hampton is about 10 miles, East Hampton to Montauk is about 15) make cycling between towns a real commitment.

When to Go: Peak summer (July and August) delivers the full Hamptons experience — packed beaches, buzzing restaurants, social energy, and the highest prices. June and September are the sweet spot — warm enough for swimming, significantly less crowded, and hotel rates 30-40% below peak. October brings harvest season, wine events, and gorgeous fall color. May is pleasant for cycling and wine tasting, though the water is too cold for comfortable swimming. Most restaurants and attractions are open from May through October; winter options are limited.

Accommodation Strategy: Summer weekend rates are brutal — $300-700/night for anything decent. The smartest strategies are visiting midweek (rates drop 40-60%), booking in shoulder season, or staying in less fashionable towns like Hampton Bays or Riverhead for significantly lower prices with easy access to the same beaches. Airbnb and VRBO offer house and cottage rentals that can be economical for groups. For a weekend splurge, Gurney’s Montauk ($550+/night) and Topping Rose House in Bridgehampton ($600+/night) are worth it. For value, The Baker House 1650 in East Hampton ($180/night midweek) is hard to beat.

Beach Access: Most Hamptons village beaches charge for parking — $25-50 per day for non-residents in summer. Some beaches require resident parking permits that visitors cannot obtain. Strategies include arriving early (before 10 AM), parking in town and walking, or using beaches in Hampton Bays and Montauk where parking is cheaper or free. The beaches themselves are public below the high-tide line under New York law, regardless of whose property fronts them.

Dining Reservations: In July and August, reservations at popular restaurants should be made days or weeks in advance, especially for weekend dinners. Nick & Toni’s, Dopo La Spiaggia, the American Hotel, and Topping Rose House all require advance booking. Lunch is generally easier, and the farm stands and casual spots (Lunch, the Clam Bar, Bostwick’s) operate first-come, first-served.