Welcome to the North Fork of Long Island: the lesser-known and more affordable sibling of the Hamptons. This region is abundant in vineyards, roadside farm stands, and adorable small towns. Only a 2-hour drive from New York City, the North Fork makes an excellent day trip, weekend trip, or even a full week’s trip.
I spent the weekend in North Fork at the end of this past July for a much-needed girl’s weekend. Over the course of 30 hours, we managed to visit three different wineries in the region as well as grab dinner at Shelter Island nearby. The beauty of the North Fork is that most of the vineyards are located right next to each other, which makes for easy transport.
There is public transportation that can take you out to the North Fork, but I would highly recommend driving for the flexibility. The route is relatively easy and can be completed in just over 2 hours from NYC.
Update: since first visiting the North Fork in 2023, I’ve gone back several times over the summer of 2024. I love this area! Since I’ve learned a few new things, look for updates to each of the sections below in smaller font.
Where to Stay
Wanting an authentic North Fork vineyard experience, we chose to stay on site at one of the vineyards we planned to visit: Jamesport Vineyard. I booked two rooms for our group of 4 people about three months before the trip. Upon arriving, we learned that our two rooms were located in a 19th century refurbished farmhouse. The house was so cute (see below)!
When we stayed here, we booked the only two rooms available online. As such, we had the entire house to ourselves. While not the cheapest accommodations, we had an amazing experience staying here. I would definitely recommend it for anyone looking to treat themselves or celebrate a special occasion.
We checked into our rooms at Jamesport at around 11am on Saturday, but didn’t end up spending time at the winery until the next day. Instead, we embarked upon a busy day of vineyard hopping. Keep reading to find out more.
More recently, I’ve stayed at Airbnbs in the town of Southold – this is a great area to base yourself in as well.
Vineyard #1: Kontokosta Winery
One of my favorite vineyards, Kontokosta is a popular spot located at the very tip of the North Fork in Greenport. Although the vineyard is popular, its also huge. We spent three leisurely hours here on a beautiful Saturday and never felt crowded for space. For a vineyard with a water view, Kontokosta is hands-down the winner.
We made a reservation online for a table about a month before going, which I’d recommend. Upon arriving, we were able to choose between sitting indoors and outdoors (outdoors, always). We then ordered wine flights and a customized cheese & charcuterie board for lunch.
After eating enough cheese to fill a family of twelve (I highly recommend the goat cheese), we walked down to the edge of the water. Kontokosta’s vineyards are located on the top of a cliff which overlooks the ocean. The views from the edge of the overlook are beautiful. You can’t walk along the sandy beach. However, there are picnic tables set up in the shade where you can enjoy a bottle of wine while taking in the view.
Kontokosta mostly sells white wines, and some reds – there is only one rosé on the menu, but we ordered it.
The edge of the cliff overlooking the ocean provided a beautiful photo backdrop that we certainly took advantage of. The grounds of the vineyard are super spacious and there were a lot of large groups, families, and couples milling about.
Vineyard #2: Croteaux Vineyards
Who doesn’t love a glass of rosé wine in the summertime? Our second stop on our North Fork vineyard tour brought us to Croteaux Vineyards, which is an entirely rosé-focused winery. They weren’t kidding: the menu listed 10+ varieties of rosé, and everything was pink.
I’d note that Croteaux does not take reservations, but my group of 4 waited for only five minutes on a busy Saturday afternoon. The outdoor space is quite large. While we waited, we browsed the cute vineyard merchandise that was for sale – think candles, sweatshirts, jewelry, and of course rosé – and the time passed very quickly until we were seated.
We all ordered only one glass of rosé each, as we had already had a few glasses at Kontokosta. Croteaux also has a limited food menu (we ordered lobster roll sliders and fries). I enjoyed sitting at the cute picnic tables in the garden, which were decorated with old fashioned bedspreads – this added such a quaint touch!
All in all, we spent about two hours here, and I can’t wait to return. The décor and vibe was unmatched and I can’t wait to try more of their rosé wines!
Dinner: Sunset Beach at Shelter Island
For dinner, we dared to venture off the beaten path to an establishment that was not technically a winery!
I had been looking to visit Shelter Island for some time, and was excited that our North Fork trip provided the opportunity to head across the water. I nabbed an 8pm dinner reservation for our group at Sunset Beach (reservations are on Resy, released 14 days in advance at midnight). We were all looking forward to sitting down for a real meal after a day of sampling different wines.
Getting to Sunset Beach proved a little harder than I had anticipated. There is a ferry that shuttles passengers between Greenport, Long Island and Shelter Island. We drove our car to Greenport, left it parked in the ferry’s lot, and boarded the ferry on foot. The ferry brought us across to Shelter Island in less than ten minutes, which was easy. However, upon reaching the other side, we abruptly realized we needed a car to get from the ferry station to our dinner reservation. While Shelter Island is small, it’s not that small!
We ended up calling a taxi (Shelter Island Taxi Service) to take us from the ferry station to dinner, and back again. While this worked out fine, it was expensive ($40 each way for a 5 minute ride). Given this, I would highly recommend just driving your car onto the ferry and using your own vehicle when on Shelter Island.
Sunset Beach was a really fun spot, with a more dancey, nightlife vibe than the peaceful vineyards where we had spent our day. The Sunset Beach hotel was jam-packed with the crème de la crème of Long Island. I’d love to come back here and spend a few nights at the hotel and relaxing by the beach.
Sunset Beach had a party atmosphere that spanned across the establishment. We spent the night singing along to ABBA and The Bee Gees at our dinner table, but also enjoyed the bar scene.
For another dinner idea, try The Halyard in Greenport – this spot had amazing views, drinks, and food. And it’s a little easier to get to than Shelter Island. Make sure to make a reservation in advance!
Vineyard #3: Jamesport Vineyard
We wanted to spend some time at our own vineyard where we were staying for the weekend, so made a point to grab a glass of wine over lunch on Sunday. Jamesport Vineyard is the only vineyard we visited with an extensive food menu. Little Oak Kitchen, their restaurant on premises, served us an excellent lunch of wood-fired pizza and wine. We loved strolling around the gardens. I’d recommend making a reservation in advance at this link.
While Kontokosta Vineyard was beachy with beautiful views, and Croteaux Vineyard was rosé-focused, Jamesport Vineyard has a garden-like feel. Jamesport has beautifully landscaped gardens, and we enjoyed strolling among the various flowerbeds with our glasses of wine.
We sat down for lunch and wine right at 12 o’clock. Jamesport was probably the least busy vineyard of the three that we visited, which I found refreshing. The wood-fired pizza was to DIE for, as were the roasted olives.
Vineyard #4: Rose Hill
I didn’t discover this vineyard until last year, but it’s one of my favorites now. Delicious rosé options, an adorable gift shop, plenty of seating, and they even allow dogs!
You don’t need to make a reservation here, but your group size has to be 8 people or smaller. I’ve never had any problem with being seated because the space is fairly large, with options indoors, on the patio, and out on the lawn.
Bonus Stop: Shopping in town and at roadside markets
As if all the gorgeous vineyards and vistas weren’t enough, this area has an abundance of adorable little stores and open-air markets. I listed a few here that I visited, but you don’t have to go out of your way to visit these spots specifically – you’re sure to come across your own as you drive through the region. Specifically, roadside farm stands were plentiful (I even saw one with a petting zoo!).
For a sweet fix, stop by Junda’s – it was right down the road from Jamesport Vineyard. We picked up a box of cookies, a chocolate croissant, and a mini apple pie. This place is a little hole in the wall (doesn’t even have a website for me to link to). We loved the baked goods – I highly recommend the Italian rainbow cookies.
To finish off our weekend, we stopped at a few roadside farmer’s market stalls on our drive back from North Fork to New York City. I unfortunately couldn’t pick any produce up because I had to travel during the upcoming week. The rest of my group picked up corn, tomatoes, and other fresh produce. I’d love to come back here and shop for the ingredients for a home-cooked meal.
Although I visited the North Fork in the summer, I think it would be an excellent destination for the spring/fall as well. I would love to visit again in a few months.
If you’re planning a trip to the nearby Hamptons instead, you can check out my other post on spots to hit in Montauk. Let me know what you think!
