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traditional · WASP · old money · tennis whites

The first English-speaking settlement in New York: settlers from Lynn, Massachusetts landed in 1640, and the colonial street pattern is still there. Gin-and-tonic country, hedge-row estates, the Meadow Club, the Southampton Hospital benefit. Less trendy than East Hampton, more traditional.

Good for: Coopers Beach, the Southampton History Museum, classic Hamptons.

Skip if: You want to feel young and edgy.

residential · quiet · art

Tiny hamlet between Southampton and Bridgehampton, named for a water-powered grist mill that has been grinding since about 1644 and still works. The windmill on the Village Green is a different building: the Corwith, hauled over from North Haven in 1813. The Parrish Art Museum is here too, at 279 Montauk Highway. Mostly residential, very quiet.

Good for: The Parrish Art Museum, the working grist mill, a discreet base.

Skip if: You want any street life at all.

farmland · central · open sky

The agricultural belt. Open potato fields, the Topping Rose House, and twenty years of Town planning aimed at keeping the Sayre Fields in open space and agriculture. Geographically central, which makes it a useful base. The public polo at Two Trees Farm ended in 2015 and has not come back.

Good for: Anyone driving to multiple villages; farm fields; a central base.

Skip if: You wanted a walkable village center.

estate · rural

Mostly farmland and estates, cut by two ponds: Georgica and Wainscott. It does have a business district, which the Town's own hamlet report describes as arranged "less like a compact walkable village and more like a strip mall" - the politest available phrasing.

Good for: People renting a house and not leaving it.

Skip if: You want anything walkable.

polished · boutique · manicured · quiet luxury

The most manicured of the villages: whitewashed shingle, luxury storefronts, and a center that is genuinely walkable and pretty. The Town's own planners describe its conversion from village center to seasonal, high-end retail; the unincorporated hamlets just outside kept their informal local flavor.

Good for: Shopping, gallery hopping, beach clubs, people-watching.

Skip if: You hate dress codes and reservation culture.

quiet · tiny · farm-to-table · beachy

Wedged between East Hampton and Montauk. The smallest of the major hamlets and proud of it. Stephen Talkhouse for live music, Indian Wells and Atlantic Avenue for the ocean beaches, the green at Amagansett Square, and the Amagansett Farmers Market a short walk on from it.

Good for: Couples who want to disappear, Indian Wells Beach.

Skip if: You need nightlife or shopping.

surf · fishing · casual · outdoorsy

Laid back, salty, surf-and-fish. Montauk Harbor is the number one commercial fishing port in New York State, and the Town's own hamlet report still calls the place a quaint fishing village. The lighthouse, the cliffs at Camp Hero, and Ditch Plains define it. Flannel and flip-flops are formal wear.

Good for: Surfers, anglers, hikers, people who think East Hampton tries too hard.

Skip if: You want fine dining and boutique shopping without driving 20 minutes.

artsy · walkable · literary · indie

An old whaling port that became the Hamptons' bohemian alternative. Walkable Main Street, Windmill Park and John Steinbeck Waterfront Park on the harbor front, the cinema. Writers and editors live here; Steinbeck got a park out of it. Faces north onto the bay, so the light is different.

Good for: Walking after dinner, the cinema, harborside drinks.

Skip if: You came for ocean swims (the bay beaches are calm but not surfy).