Beaches, seafood shacks, and great hikes: a weekend in the Hamptons

Details in this story were updated in September 2024.

My husband and I met at a beach bonfire in the Hamptons on a dreamy night under a wide sky full of stars. We had both spent many years renting beach shacks with friends in the Hamptons. Our experience was the antithesis of the glamorous reputation that usually defines this string of towns on the eastern tip of Long Island. While other visitors were drinking rose at glitzy nightclubs, we were wandering along quiet hiking trails. We loved going to roadside seafood shacks instead of fancy restaurants. Rather than gallery openings, we would head to the beach and admire the special light that has long attracted artists and painters. Eventually, we scraped our pennies together and bought a beach house in Amagansett, a sleepy little town with double dunes that line the Atlantic Ocean. We go there with our daughter Lucy every chance we can—rain, snow, or shine.

For more than a year now, I’ve been reporting on great escapes all over the eastern seaboard for The WeekEnder. This time around, I’m opening my little black book and sharing the places that I love the most in my adopted second home. Keep in mind that since I live in Amagansett, my favorite picks are centered around the far reaches of the East End in a triangle of towns that stretches from Bridgehampton north to Sag Harbor and all the way east to Montauk. But we’ll be back in future issues to explore areas farther west, from Southampton to Westhampton.

So let’s start with the most important tip of all (something I don’t tell people when they rent my beach house in the summer). If you want to experience the real Hamptons, you should come in the off-season. Lucky for you, you’re reading this in the fall, which is the best time to visit. The weather is still gorgeous and sunny, the crowds are gone, and you can truly enjoy the Hamptons like a local.

Welcome to my secret Hamptons.

One perk of coming in the fall is that the prices of the local hotels will be a fraction of what you’ll pay in the high season. Here’s my hotel hit list.

You read about the Rockaway Hotel in our Rockaways issue; this is its sister property in Montauk and it’s just as Instagram-ready, from the yellow smiley face on the exterior to the art-filled lobby.

A few years back, this Hamptons icon was transformed from a dowdy timeshare property into a hipster hot spot. It’s also a favorite place for families, who love all the amenities, like a heated indoor pool.

A classic inn was given a mod overhaul. Have a cocktail by the fireplace, then head to the restaurant for farm-to-table eats.

A renovated 19th century mansion and estate now houses a Jean-Georges restaurant.

Set right next to a marina is this property with nautical-style rooms and suites, a cozy bar, firepits, and tennis courts.

This Japanese-inspired wellness retreat offers a spa, yoga, meditation, and more.

A funky motel from the 70s was given a sleek overhaul, but lucky for travelers, they kept the rates reasonable.

Get ready to eat well in the Hamptons. But a heads up: Some of the locations here close for the season from late September to May, so if you’re not planning a trip in the high season, check to make sure they’re still open. And in case you’re wondering why some of the better-known restaurants didn’t make the cut, remember: There are many great places, but this is my insider’s list.

Hampton Chutney Company in East Hampton: Addictive dosas (crispy Indian crepes) filled with your choice of ingredients.

Mr. John’s Pancakes House in Montauk: It’s nothing to look at, but this 50-year-old family-run restaurant is famous for its pancakes—and worth the wait.

Estia’s Little Kitchen in Sag Harbor: A simple roadhouse with Mexican-inspired dishes like the veggie-stuffed Big Al’s Burrito (named after Alec Baldwin, a regular).

Fairway Restaurant in Bridgehampton: There’s nothing fancy about this diner on the Poxabogue golf course, but it’s a slice of old-school Hamptons before it got glam.

Carissa’s Bakery & Restaurant in East Hampton and Amagansett: This James Beard Award-winning bakery serves artisanal croissants, cakes, and more. People are obsessed with the pickle rye bread—sounds strange but it’s delicious.

Grindstone Coffee and Donuts in Sag Harbor: Owner Kyle Shanahan was clearly influenced by his celebrity chef stepfather Michael Symon: His brioche donuts are otherworldly.

Rowdy Hall in Amagansett: This upscale pub (think French onion soup, fish and chips) recently moved from East Hampton to Amagansett, and I couldn't be happier.

Joni’s in Montauk: A surfer hangout with a crunchy vibe, healthy wraps, and killer chai tea.

Bostwick’s Chowder House in East Hampton: This laid-back seafood restaurant is my family’s go-to when we’re craving fish tacos and steamers.

Clam Bar at Napeague in Amagansett: Set right off the highway on the Napeague Stretch between Amagansett and Montauk is the Clam Bar, a chilled-out open-air restaurant. Order the traditional clam bake.

Lobster Roll Restaurant in Amagansett: Across the street from the Clam Bar, the red-white-and-blue Lobster Roll (a.k.a Lunch) is a bit more popular, thanks to its starring role in the TV show The Affair, but I prefer the food at the Clam Bar.

Clam and Chowder House at Salivar’s Dock in Montauk: The fish comes right off the docks that morning, and the tuna sushi is particularly sublime. A tip: it’s crowded at dinner, but you can usually get a seat at lunch.

Duryea’s Lobster Deck in Montauk: This dockside restaurant was bought and revamped by a billionaire and now has billionaire prices to match (like a $68 lobster Cobb salad).

Dock House in Sag Harbor: This humble shack is a prime place to check out Sag Harbor’s megayachts. And the seafood isn’t bad, either.

La Fondita and Coche Comidor in Amagansett: Order authentic Mexican bites at La Fondita and dine at the al fresco picnic tables. Or go upscale at its sister restaurant, Coche Comidor, set in a classic silver diner.

Sen in Sag Harbor: Excellent sushi and other Asian specialties, like a divine BLT Ramen.

Street Food in Montauk: The Asian-inspired street food (poke bowls, dumplings) pairs beautifully with the beer from Montauk Brewery, located right next door. A tip: You can get beers to go and enjoy them at Street Food.

The 1770 House in East Hampton: Upstairs is a high-end restaurant, but take my advice and head to the downstairs pub, which has a cozy vibe and is famous for its meatloaf.

The Crow’s Nest in Montauk: Sean MacPherson, who is known for hip NYC hotels like the Maritime and the Bowery, converted an old seafood restaurant into one of the most stylish restaurants on the East End. Stick around after dinner for s’mores by the fire pits.

Navy Beach in Montauk: A former dive bar-turned chic restaurant right on the water.

Harvest on Fort Pond in Montauk: Great Italian food with big family-style plates for sharing.

Lulu Kitchen & Bar in Sag Harbor: This Mediterranean bistro is known for its wood-fired dishes. I dream about the heirloom cauliflower topped with grapes, yogurt, and more.

Almond in Bridgehampton: Across from each other in the center of Bridgehampton are two competing French bistros: Pierre’s and Almond. My advice: Head to Almond for truly delicious farm-to-table dishes.

Montauket in Montauk: It’s a dive, but the sunset is beyond gorgeous. When the weather’s good, everyone gathers for cocktails on the deck, but I love going even in the dead of winter.

The American Hotel in Sag Harbor: A drink here is a must: The bar feels like something from another era and is full of eccentric Hamptons types.

Of course, you can’t beat the beaches in the Hamptons: They’re stunning, no matter where you go, from the ocean to the bay. Here’s my list of things to do when you get tired of lounging by the sea.

There are so many stunning hiking trails in this area, and the East Hampton Trails Preservation Society lists many of them on its website. Here are four that I love.

Promised Land Trail in Amagansett: A gentle two-mile stroll passes through pine trees and beach grass, ending at a windswept bayside beach.

Walking Dunes in Napeague: This very special trail passes by constantly shifting 100-year-old dunes. It’s located at the end of Napeague Harbor Road and hard to find — but worth it.

Camp Hero State Park in Montauk: Everyone knows the lighthouse in Montauk; insiders head to this nearby decommissioned military base.

Elizabeth A. Morton National Wildlife Refuge in Sag Harbor: Bring birdseed: The birds will land in your hands and literally eat from your hand.

The Hamptons has long been known as a hideaway for creative types, which you can read about in Hamptons Bohemia: Two Centuries of Artists and Writers on the Beach, one of my favorite books about the area. Here are some cultural highlights not to miss.

Pollock-Krasner House and Study Center in East Hampton: Jackson Pollock’s house in the Springs is a unique local treasure that offers tours. Fun fact: You can put on booties and walk across the splatters the painter left on the floor of his old studio.

The Art Barge in Amagansett: Kids and adults can take art classes and see exhibitions at this 500-ton World War I Navy barge with beautiful views of the Napeague Harbor.

South Fork Natural History Museum in Bridgehampton: A wonderful destination to learn about the ecology and animal life of this region and go on self-guided and guided nature walks.

Hamptons International Film Festival: Every October, this don’t-miss festival showcases a wide spectrum of international films and filmmakers.

Thanks to its fertile land, the Hamptons has a rich agricultural heritage. While some of the local farms have been sold off to developers, many still exist — and have farmstands featuring the bounty of the East End. These are my picks.

Vicki's Veggies in Amagansett: This sweet little farmstand carries local tomatoes, homemade breads, and other seasonal treats. If you’re lucky, you’ll get one of the home-baked pies, but they sell out fast.

Amber Waves in Amagansett: This non-profit market and café on Main Street sells everything from produce to flowers to the freshest salads you’ve ever eaten.

Balsam Farms in Amagansett: Owner Alec Balsam is a local who started farming when he was just 13 years old. Now his farmstand is a destination where the artfully styled produce is an Instagrammer’s dream.

Round Swamp Farm in East Hampton: Fancy prepared foods (including a cult-like guacamole), but beware of the shockingly expensive prices.

As you might expect, the shopping in the Hamptons is next level. I can’t list everything, so these are my all-time favorites.

Lazypoint Variety Store in Amagansett: A beautifully curated clothing and accessories shop with pieces from Africa and Brazil.

The Monogram Shop in East Hampton: You’ll want to put your name on everything you own when you see this shop’s monogrammed products. I am obsessed with the plastic cups emblazoned with phrases like “Beach House” and “Pool.”

Sage Street Antiques in Sag Harbor: IMHO, the best antiques store on the planet. But be aware that it is only open on Saturday and Sunday, with limited hours.

Sylvester & Co. Modern General Store in Sag Harbor: Looking for a hostess gift? You’ll find it at this upscale general store with goods for the home, an excellent book section, and gourmet treats.