Road Trips

Five Days in the Hamptons

The Hamptons & North Fork: a Five-Day Road Trip

Words by WildsamPhotography by Landon Nordeman



16 May 2024

Reading Time

10 minutes

Distinguished by its reputation for summer glamour and as an elite place of respite, in actuality, the Hamptons is a landscape of complex and fascinating dynamics. Celebrities and mansions, yes–but also artist colonies, fisherfolk, farming communities and access to a vibrant stretch of the natural world. This tapering expanse at the end of an island makes for deeply textured adventuring. Photographer Landon Nordeman packed up a vintage Porsche and took to the road to trace the dynamic personality–one of rich multitudes–of the Hamptons.

This road trip started at the Behind The Fence Gallery in Southampton and ended at the Big Duck in Flanders, via Montauk, Shelter Island, and Greenport; it leans towards the natural and creative worlds. Nordeman grew up spending summers in Southampton and now visits his parents every August with his own family. For this particular journey, he brought his friend Hartje along.

This far end of this island rewards an explorers’ mindset–come along for the ride.

Miles Traveled



1981 Porsche 928, Bamboo Beige

Views from Montauk Point
Flowers from KK the Farm
Day 01

Choose Your Beach

An inconvenient but important truth: In the Hamptons, beach parking is a complicated affair, with many spots limited to cars with residents' passes. There are also beautiful beaches where visitors can pay to park. You just have to know where to go. (Rather not pay? Ditch the car; beaches like Georgica and Indian Wells are easily accessed by bike or foot.)

Ditch Plains Beach
Ditch Plains Beach

Foster Memorial Beach

The locals call this Long Beach, and it is long indeed—about a mile from end to end. You’ll want to stay for a sweeping sunset over the bay. Unlike many Hamptons beaches, Long Beach allows you to buy a day pass at the toll booth.

Lunch rec: lobster rolls from Harbor Market and Kitchen

Sagg Main Beach

Behind some of the area’s grandest estates lies one of the most desirable places to hang out on a summer afternoon, especially if you favor a gentle surf break.

Lunch rec: pulled pork sandwiches and whoopie pies at TownLine BBQ

Mecox Beach

One of the most beautiful and serene spots of sand in the Hamptons.

Lunch rec: a picnic of whatever’s fresh at the Milk Pail.
Southold Town Beach

Atlantic Avenue Beach

The surf can be heavy here, which is why you’ll see lots of guards. But the beach is worth it: miles of sand, a great view and an epic Hamptons scene.On weekdays, out-of-towners can pay $50 to get in.

Lunch rec: fresh focaccia and fish at il Buco al Mare

Kirk Park Beach

Ten years ago, there was little to no competition at this beach, which still offers parking for nonresidents, even on the weekends (for a price). Arrive early enough to secure a spot and beat the crowds, and you’ll be rewarded with an achingly beautiful view, soft sand and—if you’re lucky—a pod of playful whales spouting offshore.

Lunch rec: flat-top-seared burgers at John’s Drive-In
Ice cream at John's Drive-In
Lobster Rolls
Beach snacks at Ditch Plains Beach
Day 02

South Fork Art-Hopping

The East End’s landscape and quiet have long drawn artists, so it’s no surprise that the area hosts a rich array of art institutions.

Exploring the Parrish Art Museum

Start at the Parrish Art Museum—the long, barn-inspired building is itself a work of art. Rotating exhibitions showcase an impressive range of pieces by Long Island-rooted artists; the museum holds the largest public collection of impressionist William Merritt Chase. Break for lunch in Amagansett (tortas at La Fondita. before heading up to the Pollock-Krasner House, where a walk through the abstract expressionists’ home and studio provides an intimate glimpse of the lives behind the works. While you’re in Springs, stop by the The Springs Tavern, known as Jungle Pete’s in the days when Pollock and Willem de Kooning bent their elbows there. Or keep the creative mood going at Channing Daughters Winery, where weird and wild sculptures by Walter Channing (father of the eponymous daughters) pepper the grounds and winemaker Christopher Tracy crafts a killer pét-nat.

The Big Duck
Lights at Sunset Beach
Day 03

Exploring shelter island

Tucked between the two forks, this small, quiet island is well worth the ferry ride.

The way to Shelter Island


Mashomack Coastal Preserve

At this 2,350-acre preserve, walking trails meander among forests andcreeks. Start your day with the easy, accessible Joan C. Coles Trail, ortackle the 3.4-mile Green Trail.


Wades Beach

Shelter Island is home to a number of pristine bay beaches. At Wades Beach, gentle waves and warm water beckon—though do bring a beach chair. The sand is a rocky, shelly mix.


Marie Eiffel Market

Cafe or market, no bad choices: Marie Eiffel's breads and pastries are legendary on Shelter Island, though her market also serves sandwiches, burgers, pastas and more.


Sylvester Manor Educational Farm

Learn about what’s native to Shelter Island, and what produce grows here. Stop at the farm stand to see what’s local and fresh.

Sylvester Manor began as a plantation. Today, it is a sustainable farm, and its stewards seek to preserve and share its history. Curator and archivist Donnamarie Barnes works to tell the stories of the enslaved and Indigenous peoples of this place; check the manor’s website to keep up with events and exhibitions.

Farm bounty

Crescent Beach

Many call it Sunset Beach, for the event and for the hotel and restaurant that bear that name. Time it right to watch the orange orb fall into the bay, cocktail in hand.


18 Bay

Reserve your table in advance and enjoy the Italian-inspired culinary stylings of Elizabeth Ronzetti and Adam Kopels across a locally inflected multicourse meal.

Sunset on the Shelter Island Ferry
Day 04

North Fork Wine-Tasting Tour

With diverse grapes, wine styles and tasting experiences, Long Island wine country has something for every palate. More than three dozen tasting rooms dot the two primary roads that stretch roughly 30 miles from Riverhead to Orient Point.

The Memory Motel in Montauk

Sparkling Pointe

The area’s only strictly-sparkling winery makes classically styled wines from the grapes of Champagne, as well as some creative takes. Pops of color–artwork, geodes–decorate the Brazilian Carnaval-inspired tasting room.


Macari Vineyards

The Macari family’s twin emphases on sustainability and hospitality–including tastings in private glamping tents–are reason enough to visit. The wines are also among the region’s best, and don’t skip the cheese and charcuterie.


Croteaux Vineyards

Another specialty winery: here, it’s rosé all day–sparkling and still, mostly from merlot clones, but also cabernet franc. Step into the small tasting room, which opens onto a garden surrounded by historic barns, and you’ll swear you’ve been transported to the French countryside.


Paumanok Vineyards

On top of excellent examples of cabernet franc, chardonnay, sauvignon blanc, merlot and petit verdot, second-generation winemaker Kareem Massoud also makes the area’s best rieslings and a chenin blanc with a near cult-like following.


Lenz Winery

At Lenz, the tasting barn and courtyard are as classic as the wines. Local standards merlot and chardonnay dominate, but winemaker Thomas Spotteck also crafts outstanding sparkling wine and the rare, delicious East End cabernet sauvignon.


Bedell Cellars

Veteran winemaker Rich Olsen-Harbich’s wide-ranging portfolio includes the local stars (merlot, cabernet franc, chardonnay, sauvignon blanc) along with less common grapes like malbec and viognier–but made using ambient yeasts and less new oak than most.

Garden walks
Day 05

Farm-Fresh Bounty

Take in a sampling of the North Fork's vast array of farm stands and farmlands.

Treiber Farm

Small farms old and new dot the North Fork, from U-pick fields to farm stands galore, many of them within a potato’s throw of the hamlet of Southold. Get the lay of the land, and maybe learn a thing or two, at the Agricultural Center at Charnews Farm, one of the Peconic Land Trust’s stewardship hubs. The grounds are open to the public, so you can wander the community garden and see the range of farm operations that use the land as part of the trust’s Farms for the Future initiative. A number of excellent nearby farm stands beckon, including KK’s The Farm (an organic veggie favorite), Deep Roots (help yourself at this charming self-serve spot) and Treiber Farms (where sustainable ag and art mingle). In summertime, grab a bucket and pick your own organic berries at Bhavana Blueberries. To round out a farm-forward day, treat yourself to dinner at North Fork Table & Inn, where fresh inspiration from local farms (and vineyards and waterways) informs chef John Fraser’s ever-evolving menu.

Berries from KK the Farm
Treiber Farm

About the Photographer

Landon Nordeman lives in NYC with his wife and three sons and teaches at the International Center of Photography. If he’s not working on something photography-related he might be found adding ice to a cocktail—or at an ice rink—but not at the same time.

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