Beaches, Seafood Shacks, and Great Hikes: A Weekend in the Hamptons


Why we love the Hamptons, New York

There’s a secret side to the East End of Long Island.

Farmstands, seafood shacks, great hikes, and more.

Forget summer — fall is the best season of all.

This is from The WeekEnder series: local insider guides for new destinations a short drive from New York City, delivered to your inbox twice a month. Sign up here!

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.

Laura Begley Bloom

Laura Begley Bloom

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, avoid August, when the traffic is a nightmare, the beaches are packed, and people wait in line forever to get a coffee and a croissant. 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.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

Editor’s Note: Your safety is our primary concern. We encourage you only to travel when it’s safe to do so. While we’ve vetted businesses featured here to ensure they are adhering to the state’s current COVID requirements, the situation is fluid. If you’re not comfortable traveling, save this guide for a later date, as all these activities will be just as amazing in the future as they are today.

For more info on travel within New York, visit the state’s official COVID-19 information page.

Map of the area

1. Elizabeth A. Morton National Wildlife Refuge

2. Baron’s Cove

3. Topping Rose House

4. The Maidstone

5. Pollock-Krasner House

6. Wolffer Kitchen

7. Promised Land Trail

8. Clam Bar at Napeague

9. Walking Dunes

10. Gurney’s

11. Montauket

12. Camp Hero State Park

Where to stay

Hero Beach Club

Hero Beach Club

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.

For Instagrammers: Hero Beach Club in Montauk

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.

For families: Gurney’s in Montauk

A few years ago, 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.

For sweethearts: The Maidstone Inn in East Hampton

A classic inn was given a Scandinavian-style overhaul. Have a cocktail by the fireplace, then head to the restaurant for Swedish-modern cuisine.

Topping Rose House (L), Shou Sugi Ban Inn (R)

Topping Rose House (L), Shou Sugi Ban Inn (R)

For foodies: Topping Rose House in Bridgehampton

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

For boaties: Baron’s Cove in Sag Harbor

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

For wellness seekers: Shou Sugi Ban Inn in Bridgehampton

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

For a cheap sleep: Haven in Montauk

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

Where to eat and drink

Clam and Chowder House at Salivar’s Dock

Clam and Chowder House at Salivar’s Dock

Get ready to eat well in the Hamptons. But a heads up: Some of the locations here close for the season in late September, so if you’re not planning a trip in the next couple of weeks, 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.

BEST BREAKFASTS

Hampton Chutney Company (L), Estia’s Little Kitchen (R)

Hampton Chutney Company (L), Estia’s Little Kitchen (R)

Hampton Chutney Company in Amagansett: Addictive dosas (crispy Indian crepes) filled with your choice of ingredients. A note: It’s moving to downtown East Hampton in December.

Springs General Store in East Hampton: Jackson Pollock used to frequent this charming country-style grocery store. Grab breakfast sandwiches to go and eat them by the water at nearby Louse Point.

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

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.

COFFEE AND A SNACK

Carissa’s Bakery & Restaurant

Carissa’s Bakery & Restaurant

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.

LUNCHTIME

Rowdy Hall (L), LT Burger (R)

Rowdy Hall (L), LT Burger (R)

Rowdy Hall in East Hampton: Upscale pub grub, from French onion soup to fish and chips.

Dockside Bar & Grill in Sag Harbor: A nautical-inspired restaurant in the old American Legion with modern American cooking (like a tuna wrap with wasabi aioli) and great harbor views.

LT Burger in Sag Harbor: Seriously good burgers and boozy shakes from chef Laurent Tourondel, who gained a reputation with his New York City restaurant, BLT Steak.

SEAFOOD SHACKS

Clam Bar at Napeague

Clam Bar at Napeague

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.

Bostwick's Chowder House (L), Duryea's Lobster Deck (R)

Bostwick's Chowder House (L), Duryea's Lobster Deck (R)

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.

GLOBAL FLAVORS

La Fondita

La Fondita

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 new 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.

DATE NIGHT

Wolffer Kitchen

Wolffer Kitchen

Wolffer Kitchen in Amagansett: The Wolffer Estate Vineyard opened this lovely restaurant, where the food is healthy (nothing fried) and the wine selection is epic.

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 (L), Almond (R)

Navy Beach (L), Almond (R)

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.

COCKTAILS

Montauket

Montauket

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.

What to do

Camp Hero State Park

Camp Hero State Park

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.

BEST HIKES

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.

ARTS AND CULTURE

Pollock-Krasner House and Study Center (L), South Fork Natural History Museum (R)

Pollock-Krasner House and Study Center (L), South Fork Natural History Museum (R)

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.

FARMSTANDS

Vicki’s Veggies

Vicki’s Veggies

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.

SHOPPING

The Monogram Shop (L), Sylvester & Co. Modern General Store (R)

The Monogram Shop (L), Sylvester & Co. Modern General Store (R)

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.

Getting there

The weekend traffic en route to the Hamptons can be epic at any time of the year. My advice: Leave before lunch or after 7 p.m. and it might take about two-and-a-half hours to drive from Midtown Manhattan to Bridgehampton.

Pit stop

Want an unexpected pit stop en route to the Hamptons? Head to Silly Lily, a quirky-cool fishing station in East Moriches. It’s owned by my friend Jay, who rents out skiffs, sailboats, paddleboards, and fishing equipment. Grab a bite at the waterfront food truck from the owners of Quogue’s Stone Creek Inn.

Watch

Grey Gardens - This documentary about Big Edie and Little Edie Beale (eccentric relatives of Jackie Kennedy) is a cult classic. You can drive by their legendary house, located where Lily Pond Lane meets West End Road. It’s much nicer now than it was in the film.

Listen

What famous musician doesn’t have a home in the Hamptons? Get in the mood for a visit with tunes from Paul McCartney (who is often spotted in Amagansett) or Billy Joel (who just built a house in the center of Sag Harbor).

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