Insider's Guide to The Hamptons by Ashton Keefe

Since moving back to the East Coast, I've been reminded that my friends and I all share a fierce love of northeast summers spent by the coast! I love recapping our escapes in the beautiful coastal destinations that come alive in the most magical way during the summer season. 

When it came time to put together our Hamptons Guide, I knew exactly who to ask! One of my dearest and oldest friends, Ashton Keefe. Ashton is a chef and culinary stylist, and has spent her summers in the Hamptons for nearly two decades (although, we both grew up summering down the shore in NJ!). 

Given her career, Ashton knows all the hottest places to be Out East. But, just like me (we're close friends for a reason), she actually prefers to experience the Hamptons in a much more low-key, relaxing way (we can do without "the scene"!).

Unlike typical travel guides that point you toward crowded, trendy spots filled with influencers and DJs, Ashton’s guide is refreshingly grounded. Instead, she’s sharing her favorite local farm stands, the absolute best spots for dessert (including the dessert to order!), which places are truly worth the hype, and which ones you can happily skip.

Welcome to Ashton's Insider Guide to the Hamptons. Whether you're planning a quick weekend getaway or a longer stay, I hope you discover a few new favorites along the way!

Warmly from the coast,

 Meg

As a Jersey Shore girl, it's hard for me to admit that some of my favorite beaches and towns are now those in the Hamptons. But after long weeks — and almost 18 years — living in New York, I, like most New Yorkers, have found refuge and a community of friends and experiences that the Hamptons is so famously known for.

While fancy parties, nightlife, and "in-the-scene" experiences are fun once in a while — especially when you're young — my version of the Hamptons is a much quieter, more intimate experience on the island: beach days with friends, tennis on weekends, rosé at home in swimsuits as the sun sets, farmstands, and quiet mornings with my family drinking coffee outside on the patio.

I find that out here, everyone loosens up a bit (dare I say, becomes friendly!). People leave the city grind behind, opting for a round of golf or a glass of wine over a traditional business meeting, open to making new friends and inviting people over — even those just cruising through town. The natural beauty and convivial atmosphere of the summer season are what make it special.

Each nook and town has a bit of a different energy, and while my experience living in a few of them does not make me an expert in all of them, here are some of my favorite insider tips for the Hamptons.

Southampton is your original Hamptons — about two hours from the city, boasting an extensive and beautiful downtown full of commercial and mom-and-pop shops. Tate's Bakeshop (home of the famous Tate's cookies) is a favorite. The blueberry or peach buckle, made only a few times a summer, is magic if you can catch it — think crumb cake on steroids. I’m a fan of the classic staples from Julia Amory, a local, with a shop in town. For a locals dinner spot, try Captain Jack's right along the marina.

Wainscott, Sagaponack, and Bridgehampton boast some of the most beautiful beaches and countryside the Hamptons has to offer. One of my favorite spots Old Stove Pub recently closed and is under new management, both excited and a bit nervous of what will come of it – stay tuned! One of my favorite spots is Elaia. Visiting with my Greek friends — who swear by the authenticity of the Greek fare — makes for a fun evening. Don’t miss the happy hour; Elaia is packed year-round. Stop by for a glass of wine at Wölffer or Channing Daughters (my favorite) or spend the day — or night around a bonfire — at Mecox or Ocean Road Beach. I love flowers from Osborn Girls Flower Stand for an honor-system, side-of-the-road experience. People buzz about Sag General Store and the chicken salad at Round Swamp — both beautiful and delicious, but admittedly hyped. My favorite part of this area is driving south of the highway (Route 27) in the early morning as the sun rises, taking in all the farms, horses, and old homes greeting the day.
Sag Harbor is considered by many the most charming of all the Hamptons towns. If you love Nantucket, Sag Harbor will be your spot — particularly for the design-and-history-inclined who may not care as much about spending the day at the beach. This town is full of Federal and Greek Revival style homes, nods to its whaling history, and a downtown perfect for families. Big Olaf's Ice Cream (cash only), a stroll past Billy Joel's home and his boat, the Alexa, and buzzy iconic restaurants like the The American Hotel (sit at the bar or on the porch) make summering in Sag Harbor a walkable destination full of photogenic homes and places. For more hole-in-the-wall spots, I love Murph's for a beer (reportedly JFK Jr.'s favorite watering hole), Il Cappuccino (a casual "Scenes from an Italian Restaurant" kind of spot), Bell & Anchor for a great locals seafood spot, Cavaniola’s for cheese, and Schiavoni's Market (third generation owned and operated). Also, don’t forget to check out the Whaling Museum.

East Hampton mixes old and new — a combination of historic homes and the most designer shops of any of the downtowns; it feels like you’re on the Upper East Side, but within walking distance of the beach. Cruise up into the Springs for a more relaxed, authentic Hamptons vibe: locals, wooded neighborhoods, and bay beaches. Watch the sunset at Bostwick's on the Harbor (kid-friendly) if you find yourself in the area at golden hour. Cruise through town south of the highway to admire the homes on Egypt Lane or take in Maidstone Club and its golf course — one of the most coveted tee times in the Hamptons. East Hampton Village requires a special beach pass, so make sure to grab one if you're spending the summer in town. Two Mile Hollow is a favorite for its bathroom facilities, larger parking lot, and the ability to pop over to Carissa's or Bostwick's Chowder House for lunch midday. Dinner is always a ten at East Hampton Grill, where celebs and locals rub elbows. For a more classic historic table, check out 1770 House (the pub in the basement is a less formal dining experience and very cozy during the winter).

Amagansett is where the surf vibes start to intensify. It’s beautiful and prestigious neighborhoods — often referred to as "The Lanes" — run like a grid leading to the beach. Catch a show at Talkhouse, perhaps running into a musicians like Sir Paul McCartney. If you’re going on a weekend, buy tickets in advance to avoid the line! For a slice or pie, stop at Fini Pizza and head to the beach to enjoy with friends and local rosé. Continue east toward Montauk, stopping at Clam Bar or Lunch (formerly Lobster Roll). It's an either/or — just ask anyone out here, everyone has their favorite.

In Montauk, drive all the way to the lighthouse, walk the Shadmoor trails (check for ticks!), venture under the chains at Camp Hero (yes, it's creepy — and reportedly the inspiration for Stranger Things), play a twilight round at Montauk Downs, catch the sunset and a beer at the Montauket, and dance all night at The Point. I love Montauk Bake Shoppe for crumb cake, the Ditch Witch for lunch while hanging at Ditch Plains (get the Ditch Witch Wrap), or Gosman's Market for cooking at home. For a scene, find someone who has a table at Surf Lodge or catch the sunset (and if you’re luck and not staying on property), a table a Crow’s Nest for dinner.

Whether you’re looking for a party or a relaxing weekend, the Hamptons is truly a choose-your-own-adventure destination full of fresh produce, beautiful beaches, pink sunsets, and all the joy and bliss that summer is made of. 

How to get there (from NYC): LIRR, ferry, car, or Jitney.

Where to stay: Faraway Sag Habor (Sag Harbor), LDV at the Maidstone (East Hampton), The Reform Club (Amagansett), Hero Beach Club (Montauk), The Corduray Hotel (Montauk), Crow’s Nest.
Favorite Farmstands: Serene Green, Pike Farms, Amber Waves, Balsam Farms, Spring Close Farm, and Vicki's Vegetables.

Want to have an extended rental or perhaps you’re so inspired you’d like to buy? The best realtor in town is Elizabeth Carey.