North Fork, Montauk and The Hamptons | Long Island

Only 75 miles east of New York City, there’s low-key seaside charm, a quiet patch of vineyards, and casual farm stands.” Condé Nast Traveler

A world away from the bright lights of Manhattan sits North Fork, a 30-mile stretch on the northeastern peninsula of Long Island. A rich, green area of coastal farmland known for its wineries, fresh produce and beaches. Just a two hour drive, traffic permitting or short helicopter ride if you are fancy, from the heart of the city and you arrive in this tranquil rural region with its stunning waterfront houses, family-owned farms and a thriving farm-to-table dining scene.

We stayed in Southold in a large, charming one-story four bedroom house just a few minutes walk from the beach booked via VRBO. After many hours, well actually days, trailing through hotel booking sites lusting after stunning boutique hotels this turned out to be the best option in terms of availability and cost. 

Greenport, North Fork’s largest town, is a quaint with vintage shops, independent cafes and restaurants and some of those aforementioned lusted after hotels. The short drive from Southold to Greenport is filled with vineyards and farm stands piled high with freshly picked, organic produce. 

Long Island’s more well-known and flashier summer escapes take place in South Fork aka the Hamptons and its neighbouring popular surf hamlet, Montauk. We took a day trip to explore that area and see how the other half live, it’s easily accessible and well organised. It’s an easy five-minute ride on the North Ferry from Greenport to Shelter Island then a five mile drive across the island to the South Ferry and another short car ferry to Sag Harbor. 

While The Hamptons is filled with ridiculously huge stunning houses and estates Montauk, although technically part of East Hampton, is less pretentious and appeared to be a more laid back surf haven. First glimpses of the glitzy lifestyle of the rich and famous can be seen in Sag Harbor which was full of mega yachts. As you go further inland the houses get bigger, the cars flashier and there’s plenty of designer shops and eateries to furnish the demands of the affluent summer crowd. This area is stunning, the coastal weather is perfect and it’s easy to see why celebrities and wealthy New Yorkers decamp here for the summer months.

Montauk, located at the most eastern point of Long Island, is scenic with beautiful beaches (Ditch Plains Beach being the most popular), state parks, hiking trails, camping sites and good surfing conditions courtesy of the Atlantic ocean. The historic Montauk Point Lighthouse sits at the tip of the peninsula but is currently closed to visitors although you can still visit the museum. It’s New York’s oldest lighthouse and can be admired free of charge from the Montauk Point State Park. 

The hamlet itself is filled with a mix of high-end hotels and motel style accommodation that caters for the surfers. There’s plenty of cafes, shops and a brewery. Famous for its Long Island fresh lobster rolls and celebrity clientele, the Lobster Roll, known locally as LUNCH, is a must do as you drive along the Montauk Highway in Amagansett. The forty year old beach shack is iconic, the menu lists its many celebrity visitors alongside its fare and it has even appeared in a Showtime TV series. 

Dining – North Fork is awash with local fresh produce, wines and craft beers so there’s lots of opportunities for some top dining experiences. North Fork Table in Southold is a must visit, an upmarket farm-to-table experience paired with fine wines and cocktails. The stylish restaurant, which also offers alfresco dining, is housed in a historic one-story building and prides itself on its use of fresh produce sourced from local fishermen, farms and vineyards. 

At its helm is restaurateur and Michelin-starred Chef John Fraser, his menu offers seasonal American cuisine with a contemporary twist complimented by modern mixology. There’s also a food truck that’s open from Thursday – Sunday (11am – 6pm) serving high-end street style food such as chicken wings, ribs, burgers and and local speciality lobster rolls.

Local ingredients also feature on the menu at American Beech in Greenport. The selection of new American fare features dishes such as buttermilk fried chicken, burgers and burrata with peas accompanied by North Fork wines and beer. The bold monochrome and pink interior is a funky and there’s an outdoor terrace and bar built around an ancient beech tree from which the restaurant and hotel get their name.

Bruce & Son is a good all-day brunch spot in Greenport. If you are looking for a warm welcome and friendly service this is not the place but the breakfast is tasty. The speciality coffee options were good using locally produced beans from the North Fork Roasting Company. Famous for its progressive and locally inspired menu, the restaurant is popular for its hot cakes and sugared bacon.

Fancy a small town rustic experience? Try Love Lane Kitchen located on a charming little street in Mattituck for breakfast but not if you are in a rush as it’s country life pace. The cafe itself is quite small but there’s also an outdoor terrace, the menu was pretty basic with some specials and they are known for their breakfast bowls. 

Wineries – This area has many attractive visitor spots but its most popular has to be its sixty plus wineries. The Long Island Wine Trail is a tourist attraction in itself and you can be forgiven in thinking you are Franschhoek in South Africa or the South of France. There are many vineyards to visit but sadly we only managed two on this short visit to the area. 

I highly recommend a visit to Croteaux, the only vineyard in United States dedicated to producing entirely rosé wine. It’s a charming set-up with its 200-year old converted barn, courtyard and tasting garden where their vintage Citroen wine truck is parked. Wine tasting flights include all their merlot rosés or regional specific cabernet franc–only rosés. Wines can be paired with a small light bites menu food including local lobster sliders and a Provençal basket. This winery is just stunning, it has the perfect vibe for a relaxing summer afternoon and the rosé was really good too.

Harbes Vineyard is less picturesque but more family friendly as there’s also a children’s farm and activities. North Fork’s first sustainable vineyard offers tasting selections of their chardonnay, merlot, chenin blanc, sauvignon blanc and cabernet franc in the wine barn or on the lawn. 

Other top recommendations in the area were Kontokosta, the region’s only waterfront winery and Macari Vineyard in Mattituck. It’s not just about the wine either as there’s plenty of local breweries to visit. Greenport Harbor Brewing Co. has two tasting rooms, the first at its original Greenport location and a larger second venue in Peconic. You can sample ales from the Montauk Brewing Company in most local restaurants and also visit the tasting room in Montauk itself. 

Accommodation – The area demands top quality accommodation and there’s a copious amount to choose from. Alongside hotels, motels and surf lodges there’s plenty of houses for any budget available on both AirBnb and VRBO. If you have cash to splash you can book an amazing house in the Hamptons. My top hotel picks would be these that were sadly not available on our dates as we booked last minute: American Beech, The Menhaden, Sound View located on the Long Island Sound and Aqua Beach Hotel in Aquebogue (sister hotel of American Beech). In Montauk my top picks were Gurney’s Montauk Resort & Seawater Spa and Marram Montauk.

Shopping – Can you even say you have been the US if you haven’t been to an outlet mall? Tanger Outlet in Riverhead is huge and has all the usual shops that you expect like Ralph Lauren, Nike, Adidas, Gap, Sunglasses Hut etc. Honestly it’s a bit too spread out and you lose momentum quickly especially when it’s hot. Disappointedly there were no high-end designer shops so if you like those I recommend a trip to Woodbury Common Premium Outlets in Central Valley, New York which is totally doable in a day trip from Manhattan.

Activities – There’s so much more to do here if you have the time. Rent kayaks and paddle boards in Southold, hire some bikes and explore on two wheels, go strawberry picking at one of the many farms, visit Lavender by the Bay lavender farm and then head to Greenport to shuck some oysters at the Little Creek Oyster Farm. There’s also hiking trails, yoga and pilates classes, golf courses, drive-in movies, beautiful beaches and boat trips. Not forgetting the local farmers markets and the local live music scene with gigs at various venues. Visit to keep up with everything that’s happening in the area.

I was pleasantly surprised by everything North Fork had to offer and I would definitely recommend visiting if you are in New York and want a break from the city. Hiring a car is a must for getting there and exploring everything the area has to offer. We stayed three nights but could easily have stayed much longer.

*We are fully vaccinated so therefore were not required to quarantine on arrival in New York. We had to complete a New York State Traveler Health Form one day prior to departure and receive a green tick for entry. A negative PCR test taken within 72 hours of departure is also required to fly and to enter the USA. We flew direct to New York from Abu Dhabi with Etihad Airways. Other airlines and states may have different requirements so check before you book.

Read more about our New York trip in previous posts In Pictures | A Postcard from New York and MADE Hotel | New York

The views in this post are all my own based on my experience. Unless otherwise stated all photos © Jo Brett 2021. All rights reserved.

3 thoughts on “North Fork, Montauk and The Hamptons | Long Island

  1. Thank you for promoting the East End of Long Island.

    I would suggest that you also mention the quaint B&Bs. The smaller businesses need the publicity too.

    Oh by the way we Long Islanders have some pet peeves: 1. We live ON Long Island 2. It’s called the THE Hamptons and THE North Fork.

    It is a well written article and those of us who live and work here appreciate all exposure if it is balanced and fair.

    1. Hi Wilfred,

      Many thanks for reaching out and your appreciation of the post. In all my articles I only write from personal experience so all the places mentioned I visited myself so its a fair summary based on where I went on my trip.

      Many thanks


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