Buckle Up! A Road Trip to the North Fork and Hamptons

Coopers Beach Southampton / Photo courtesy of Discover Long Island

— By Laurie Bain Wilson —

On Long Island’s East End, you’ll find the South Fork and North Fork. Both destinations spoil vacationing families with miles of white sandy beaches that are as celebrated as the celebrities that sun and swim here.

Long Island is surrounded by water, the Long Island Sound on the North Shore and the Atlantic Ocean on the South. There are many villages and towns — Southampton and Sag Harbor are two of the most popular towns with chic, pricey boutiques, world-renowned galleries, and star-studded restaurants. 

But the beauty of the East End is that there are also farms and farm stands everywhere, clutch for grabbing goodies for family picnics at the beach, parks, or hotels — all while promising fresh, healthy ingredients. It’s also a much cheaper idea than eating out, although there are family-friendly restaurants you should build into your itinerary.

Road Tripping the North Fork and Hamptons

Your road trip to the Hamptons will take you on the Long Island Expressway which runs west to east. You can also take a train from NYC and the Hampton Jitney, a luxury bus from the city. A ferry also travels to the East End from Connecticut. 

Note: Riverhead is your gateway to the North and South Forks as you travel from the west on Long Island. And if you’ve got aquarium-loving kids, this is a good spot for a visit on your way out east; it’s home to the Long Island Aquarium, which has one of the world’s largest living coral reefs. Riverhead was also recently named by Forbes as one of the 50 best travel destinations around the globe. The Hyatt Place Long Island/East End is a splash from the Aquarium with an indoor and outdoor pool, as well as breakfast buffet.

Here are some Hamptons/North Fork ideas for where to eat, play and stay.

The North Fork

“NoFo” is not as famous or as famously crowded as the Hamptons. Yet, it’s a trendy and immensely popular destination for those who want to avoid the Hamptons scene — or, perhaps add it to a road trip itinerary along with a few days in the Hamptons.

The North Fork is especially photogenic. You’ll find sweet roadside cottages and upscale motels, as well as 100 active farms and farm stands at every twist and turn.

There are also more than 60 vineyards on the North Fork, as well as dozens of breweries and craft distilleries — a couple, including  Bedell Cellars and Pindar Vineyards, even have family attractions.

Play in North Fork

Greenport / Photo courtesy of NYS Dept. of Economic Dev. (NYSDED)

Harbes Family Farm: You can spend an entire day at this Mattituck farm with musical hayride tours, farm animals, sunflower fields, bounce pillows, themed playgrounds, fresh fruit and veggies and lots more family fun.

The East End Seaport Museum: This spot on the waterfront in Greenport celebrates the maritime legacy of the East End. The Seaport Museum features artifacts, exhibits, and a Village Blacksmith Shop, with plenty of hands-on experiences for kids to explore.

And those beaches! Eagles Neck Paddling Company rents kayaks and canoes for family water fun. 

Stay in North Fork

Silver Sands / Photo courtesy of Discover Long Island

Hotel Moraine: This Greenport family resort has 20 guestrooms, a spa, saltwater swimming pool, private beach, communal cottage for games, outdoor bar for sunset sips, and complimentary paddle boards. 

The Silver Sands Motel: Another Greenport motel, dating to the late 1950s, with a private beach and accommodations in beach houses, motel rooms, and bungalows. Nookies is its retro restaurant and definitely worth a taste or two (think chocolate malts, mint green swivel stools, and local oysters).

Eat in North Fork

Photo courtesy of Claudio’s Greenport

Love Lane Kitchen: It’s a love fest! Locals love this spot in Mattituck for breakfast, lunch and dinner as much as tourists do. French toast, griddle cakes, and pastrami sandwiches are popular, but the salads are equally as delectable for a more veggie-centric option. There are kid items on the menu like grilled chicken and avocado. And there are cocktails. Did we mention outdoor seating?

Claudio’s Greenport: Outdoor dining, kid’s menu (with agreeable classics like mac ‘n cheese or smashburgers), and gorgeous sunsets — a trifecta for family dining. This Greenport spot is America’s longest-running, single-family-owned restaurant dating to 1870. Baked clams, lobster rolls, and much more: Hello, summer!

The Hamptons

The Hamptons is a necklace of sandy playgrounds. Jaded New Yorkers and celebs play with all the toys here in the summer, but it’s also a perfect family spot for visitors — especially beach-loving squads. But there are other reasons to visit.

Play in the Hamptons

Coopers Beach / Photo courtesy of Discover Long Island

Southampton Golf Range: This range has a fun 18-hole mini golf course designed with East End landmarks, like the Montauk Point Lighthouse. 

Cooper’s Beach was just named the best beach in the country, according to Dr. Beach aka Dr. Leatherman. The Southampton beach is one of the few beaches where non-residents can pay to park; it’ll cost you $50 for the day, but you’ll find the best beach in America is worth the price tag. It’s a 500-foot grainy white quartz sand strand framed by large sand dunes and the Atlantic Ocean. The waves are gentle, so it’s a good spot to swim and ideal for families. There’s a snack bar, umbrella and chair rentals, and — most important — lifeguards.

Eat in the Hamptons

Photo courtesy of Camp Rubirosa

Camp Rubirosa: Many lucky New Yorkers summer in the Hamptons, and this NYC Mulberry pizza hotspot’s Hamptons location offers everyone a slice of the city. For the first time in its 15-year history, Camp Rubirosa is a seasonal pop-up in a “nostalgic, summer camp-inspired setting” in East Hampton. Think: thin-crust pizza, house-made pasta and locally-sourced seafood. There’s also an outdoor piazza.

Modern Snack Bar: Nostalgic classic feels and an iconic neon sign evokes smiles for locals and visitors who have dined on this Aquabogue spot’s milkshakes and burgers for the past 75 years. But there’s also soft-shell crab, meatloaf, bay scallops, and roasted turkey on the menu. Modern Snack Bar also has classic cocktails, like an Old Fashioned and Mojito.

Union Burger: If you’re after comfort food in Southampton, this is the spot. The Union Burger menu (including kids’ options) is jam-packed with burgers, mac ‘n cheese, and milkshakes like the Cotton Candy (vanilla fruity pebbles frosted rim, strawberry milkshake, cotton candy, whipped cream, sour patch kids and a giant lollipop). Even better, they have boozy milkshakes for the ‘rents — undoubtedly a win/win.

 Stay in the Hamptons

Photo courtesy of The Sagaponack

The Sagaponack: The nine bungalows here wow families with kitchenettes and private outdoor spaces. There are also guest rooms in the Main Inn and a porch. A pantry is stocked with goodies. Kid clutch: The outdoor heated pool and lawn games are also family faves, as are the cruiser bikes. Guests can get passes, too, for the exclusive town beach, and there’s also access to the beach locker service for lounge chairs, umbrellas, beach toys, and coolers.

The Roundtree Amagansett: Quaint Amagansett is home to this unpretentious family spot, a rambling collection of renovated cottages, houses, and barns. There’s also a beach house. The back lawn is where it’s at with a firepit, popcorn popping, s’more tasting, and stargazing galore. Beach chairs, umbrellas and other amenities are available for a day at the beach. And there are even lawn games like corn hole. Sweet: Kids can get involved with the hotel’s Lemonade Stand program to raise money for a charity. The hotel provides the supplies, including the stand and the Main Street address, and the kids make lemonade and sell it. Proceeds are donated to a charity of their choice, but parents must be on site.

Montauk

At the tip of Long Island’s East End, on the Atlantic Ocean and Block Island Sound, this fishing hamlet is in a league of its own. Geographically, it is the very tip of East Hampton.

Montauk was on the map 50 years ago this summer when “Jaws” came out; it is based on a story of a Montauk shark fisherman, although it was filmed in Massachusetts. Expect celebrations here this summer.

Play in Montauk

The beaches are spectacular; Ditch Plains beach is especially popular, especially for surfing but swimming, too.

There are also seven state parks and the historic Montauk Point Lighthouse. You can climb to the top, though kids must be 41 inches tall. There are also charter fishing boat experiences out of Montauk for visitors.

Eat in Montauk

Photo courtesy of Navy Beach

Navy Beach: A casual waterfront beach house through and through. Expect a well-rounded menu with plenty of seafood and nautical feasts, served with a side of sunsets.  

Duryea’s: Indulging in a lobster dish is summer on a plate at this waterfront restaurant. Lobster rolls, lobster cobb salad, chilled lobster, grilled lobster… The list goes on. But if anyone isn’t feeling shellfish, Duryea’s has other dishes like burgers to keep all stomachs satisfied.

Stay in Montauk

Montauk Yacht Club: Built as a private social club on Star Island within Lake Montauk, the tides have shifted through the years and is now owned by Proper Hotels. Three pools, a private beach, a spa and summery bonfires when the sun sets. The hotel also debuted the new Ocean Club Montauk restaurant last year and it’s turning heads. Love boats? This spot is home to the largest marina in the Hamptons.

About the Author: Laurie Bain Wilson’s work has appeared in Real Simple, Working Mother, OpenTable, PBS/Next Avenue, Travel Channel, CNN Travel, Travel Market Report, Eat This, Chowhound, Parents, Salon, Wine Enthusiast, VinePair, and New York Times. She is also a longtime correspondent at The Boston Globe. Find more from Laurie at weekendsandcupcakes.com and her Muckrack profile