If the Hamptons were a family, this would be the stately grandfather who has probably mastered the art of being a functioning alcoholic; someone you don’t want to mess with, but who’s a ton of fun. It’s the old-rich of the Hamptons, being one of the first settlements out east where city-folk used to escape. Lots of shops, lots of clubs, and very well-established.
Water Mill is a smaller hamlet positioned between South and Bridge that can easily be overlooked or “swept under the rug” – kinda like that 20something your dad has been running around with whom everyone seems to know about. Very quaint, very fancy, and very bourgeoisie, it’s just a hop, skip, and a jump from a party in Southampton and shopping in Bridgehampton.
Bridgehampton is a larger village and is known for its casual opulence. The main street is exceptionally beautiful, as are many of the estates you’ll find there – if you can afford them. It kinda sums up what it means to be a chic matriarch in the East End; fun, pretty, and with lots to do. Plus, this hamlet is especially historic, which can be nice when you want to take a fun day trip.
Like your wine? Sagaponack is famous for housing the popular Wolffer Estate – a winery that produces some of the best rose in the world. Though it can be easily overshadowed by East Hampton at times due to its location, Sagaponack is like that aunt in the family everyone knows about, but tends to do her own thing unless she’s throwing a huge party. And Sagaponack can have some SICK parties.
Wainscott is suburban and home-y and kinda just makes you want to sip sangria and eat fresh food all day long. It’s kind of like that one sister you had who always just wanted to grow up and have a family, like, right away. Not that we blame her – she makes great food, has awesome dinner parties, and if you ever want a place really chill, Wainscott is the place.
East Hampton is the sibling that went off to become famous, actually succeeded, and now is living the life everyone wishes they could. Perfectly preppy, but with a little edge, East Hampton offers a perfect flavor of what the South Fork represents; class, relaxation, and fun. It’s not as stuffy as Southampton and has a little bit of the Montauk flavor that doesn’t make the town unbearable aristocratic. There’s always something to do, be it sunning yourself on Main Beach or sipping cocktails at Nick and Toni’s. Plus, lots of celebs.
Bars like Indian Wells Tavern and Stephen Talkhouse make Amagansett more laid back than its East Hampton neighbor, attracting a younger, more fun crowd, but this village still has boat-loads of swankiness. Further Lane, anybody? You’re likely to find a fratty crowd partying on Indian Wells Beach, where it’s been reported its the spot to go if you’re a Hamptons Bro. Sound like your younger, collegiate sibling, perhaps? Maybe he’ll never grow up all the way, but he’s still a ton of fun.
Montauk may be a little further down Route 27, but like many middle siblings, all their friends usually love them and they’re usually seen having the most fun because they DGAF. Montauk is the place to party with the finest in the most low-key town out East. Who was that familiar looking guy you just did shots with at the Memory Motel? Oh yeah, Josh Hartnett. This is the middle child of the family who sometimes everyone forgets about due to their proximity from everyone else, but given that the village has lots of laid-back locals mixed with trendy socialites, there’s always the craziest kinds of parties to attend, whether it’s with the hamlet’s local fisherman or that actor from the newest CW show.