The Essential North Fork Long Island Itinerary & Travel Guide

By | Food, Travel, Wine, Finance and Lifestyle Journalist
Last Updated: September 29, 2022
Essential North Fork Long Island: Travel Guide & Itinerary • Winetraveler

Several years ago, I rented a beach cottage from a good friend in Orient, a town located on the farthest tip of the North Fork in the East End. That summer, when I took on freelance assignments writing about the growing wine scene, I spent a great deal of time all over town. The allure about this region, I quickly discovered, was enchanting. It wasn’t the Hamptons but it wasn’t New England either. 

What I soon came to discover was that it was a wonderful retreat from the city that included wineries, culinary experiences and beach access, the vacation trifecta in my eyes. This gem of the East End provided everything I was seeking: the aesthetic beauty of wine country with an increasingly heavy-hitting food scene that combined fine dining with casual eats.

I loved it so much that I invited my wine-loving, then-boyfriend out for a weekend, who, if I’m being honest, was skeptical of its charm. Fast forward to a year later, he proposed to me on an East Marion beach at sunset and a year after that, we were married and bought a weekend home in the town of Southold.

Since then, we’ve become North Fork converts. We even created a food and drink checklist that we constantly update. Each time a new winery, restaurant or bar opens up, we vow to try it and decide if it was good enough to keep in our local rotation or save for visitors and special events.

Within the last year or so, we’ve witnessed the expansion of the North Fork first-hand, watching some incredible local businesses pop up that are dedicated to quality food and hospitality. See below a highly-curated list of where to eat and drink from Manhattanites turned North Fork locals.

How to Get There

The North Fork is a great weekend trip for those living in the tri-state area, especially New York City. Renting a car from the New York City area is an easy way of getting out there, and expect around a two to three-hour drive from most spots in New York.

There are also buses known as the Hampton Jitney that have their own North Fork line and leave directly from several stops in Midtown Manhattan. There is also the Hampton Ambassador that boasts larger seats, reservation access and a variety of refreshments are served while onboard.

If buses aren’t your thing, the LIRR goes out to the North Fork (with a transfer in Ronkonkoma) and stops in popular towns like Southold and Greenport.

If you’d like to ride out in style, Sourced Adventures offers round-trip transportation to and from Manhattan and a full-day wine tour of the region.

Once you’re in the area, and if luxe is your thing, Family in New York offers customizable and privately guided day trips around The Hamptons, the beaches, and to a variety of wineries scattered throughout the beautiful North Fork. 

Where to Stay

If you’re looking to rent AirBNB or HomeAway, keep in mind that there is a two-week minimum rental period in place for both the North Fork and the Hamptons. With that being said, there are a plethora of wonderful rentals available that provide beach access amidst the vines. If rentals aren’t your thing, check out boutique B&Bs that offer charm, character, and of course, delicious breakfast.

Sannino Vineyards has been a mainstay on the Fork since 2006. It recently revamped its tasting room and updated its B&B offerings, which is also located on the vineyard’s property. The B&B has two rooms, a suite, and a villa, equipped with marble baths and a private balcony and patio that overlook the vineyards. Your stay also includes a complimentary wine tasting and cheese plate at the winery. The new tasting room has plenty of outdoor space to kick back and relax with friends in the warmer months. They also offer a variety of special events throughout the year worth checking out. Perhaps it’s wise to plan your stay around one of their unique activities.

Southold Harbor Inn is the new kid on the accommodations block. It is rethinking the B&B model, pairing it with elegance and luxury amongst the vines. The boutique hotel is located steps from Croteaux Vineyard and is walkable to Greenport Harbor Brewery. There’s even a wonderful local beach that is a 10-minute walk down the road for those visiting in warmer weather. The renovated 1897 Farmhouse boasts rooms with en-suite baths and luxurious rain dance showers.

Menhaden is made for the hotel lover with its Restoration Hardware finishes and spa-like bathrooms. It also has a restaurant (The Merchant’s Wife) and a roof deck bar on the property for those who are looking to unwind and not venture far from their room. The cozy rooftop has a fireplace to huddle around in the evening hours with sweeping views to watch the sun go down over Greenport Harbor.

Wineries & Bars To Visit on the North Fork

RGNY vineyard has opened recently in the older Martha Clara space. They’ve breathed new life into the property with a fresh look with different dining and private tasting spaces. The outdoor area at this winery is what it’s all about. Families, friends and pets alike hang outside playing cornhole and enjoy bites from rotating food trucks and live music every weekend.  This certified sustainable winery produces popular varieties including Rosé-style blends, Sauvignon Blanc, Viognier and Cabernet Franc, among others.

Bridge Lane Wines, a company owned by Lieb Cellars on the North Fork, is challenging the way East Ender’s think about wine. The grapes are grown on Lieb’s sustainable property and then produced into different varieties (white Merlot, unoaked Chardonnay, Sauvignon Blanc, dry Rosé red blend, and a newly-launched Bridge Lane Bubbles) and packed into fun, accessible cans. They’re perfect for picnicking on one of the island’s beautiful beaches during your stay or to take home to save for later.  

Black Llama Bar in American Beech is the new clandestine cocktail and oyster bar and lounge attached to American Beech in Greenport Village. This hot spot is a little New York City in the North Fork offering an extensive high-end cocktail menu. Snag yourself a reservation at one of the town’s local restaurants and swing by the Black Llama before or after to get your cocktail fix on.

Where to Eat

Pizza Rita began as a pizza truck a few years back but now has a brick-and-mortar location in Mattituck. This restaurant is the brainchild of classically-trained chef Jeff Marrone who has dedicated his career to making Neapolitan-style pizza in a brick oven imported from Italy. It’s also decorated with local pieces of art found out in the North Fork. Not only are his pizzas fantastic, but he also serves up outstanding, light and fluffy calzones and homemade gelato. In season, you can find the Pizza Rita food truck at many of the local wineries in the North Fork. His pies are the closest to Italy you’ll get in New York—trust me.

Ellen’s on Front in Greenport was opened by chef Jennie Werts after her successful and beloved pop-up run at Jennie’s at Drossos. This restaurant runs everyday happy hour specials that showcase local beer and wine and has been wowing guests with dishes like Korean fried duck wings, duck fried rice, and short rib grilled cheese.

Olive Branch Restaurant and Bar, located across the street from the Greenport Carousel and down the block from the trendy Menhaden, serves up traditional Turkish and Mediterranean cuisine at the hands of head chef and owner Yusuf Alptekin. Try authentic, aromatic and wonderfully-flavored dishes like a traditional lamb gyro, stuffed grape leaves and salmon shish kabob that make you think you are dining in the heart of the Mediterranean. Instead, you’re at a beautifully designed courtyard in Greenport. It’s a win-win on every level.

North Fork Doughnut Company makes life a bit brighter on your visit to the North Fork. Gathering a group of friends for a weekend away or a birthday party? Place your order with NoFo DoCo for a dozen of their specialty doughnuts to elevate the event. They often showcase a specialty doughnut weekly but also have their mainstays in rotation like black raspberry jelly, cinnamon sugar, and Boston crème. Or better yet, check to see what events local wineries are hosting in conjunction with this beloved doughnut shop. Wineries like Sannino Vineyards have teamed up with them to host wine and doughnut pairings, which makes for a great night out.

You are reading “Essential North Fork Long Island Itinerary & Travel Guide” Back To Top

best things to do in Long Island: North Fork winery list

If you enjoyed this guide, make sure you register to become a Winetraveler for free! You’ll get access to all of our content and interact with other Winetravelers and for travel inspiration around the world. Be sure to follow along with us on Instagram as we continue to feature more exciting destinations.

Get Articles Like These Directly in Your Inbox!

Subscribe to Winetraveler and receive notifications when new travel guides and itineraries are published. It's free!

Leave a Comment, Ask a Question or Share a Review

Share to...