What to Do, Where to Stay, Eat and Play in Long Island’s North Fork: The Perfect Luxury Weekend Getaway from New York City

Living in NYC is amazing…until you want to leave! And then unless you’re a VIP or Hedge Funder, your options for luxurious local getaways become quite limited! The Hamptons and now even Montauk have priced anyone who makes less than 6-figures out of the market–unless you happen to have some hospitable rich friends with a couple extra bedrooms! There are plenty of houses you can rent in the Hamptons and Montauk–many of them quite lovely! But they are exorbitantly priced, nowhere near the beach and usually they aren’t that luxurious. I’m happy to pay top dollar for a hotel room or a place to stay as long as I know it’s worth it–and the problem is that during the height of summer, many shacks that are anywhere close to the beach in the Hamptons can charge an arm and a leg and people will pay it. And don’t even get me started on the awful scene in the Hamptons. I’ve heard wonderful things about Montauk though I’ve never been. But the Hamptons is just filled with a bunch of people who are just so proud of themselves for getting there. Everyone is uber self-impressed, the taxis are overpriced and the traffic is a nightmare! Did I mention it can take 4 hours to get out there? Well, luxe-loving city people–I’ve found your solution! It’s called the North Fork on Long Island.

Long Island splits into two, on the bottom fork are the Hamptons and on North is–you guessed it–the North Fork. Here are located dozens of different vineyards, inns, cottages available to rent and adorable restaurants. While I can’t attest to the quality of wine at ALL of the vineyards, there are several that are gorgeous and have decent wine–I swear! The food though has reached epic levels as famous chefs are looking to get closer to the farms that they like to furnish their recipes with.

Where to Stay

This past weekend I headed out with my husband and a couple of friends to the North Fork to see what we could find. As you can imagine, I was a bit jittery about going out there–when there are no Four Seasons in my itinerary, I start to panic. And when my friend suggested renting an apartment or cottage, I started hyperventilating. I just always get nervous with renting homes. You never know what you’re going to get and I was quite apprehensive. Luckily, my friend struck gold when he found the cottage we chose! It was aptly named the Shades of Grey cottage-luckily not for the book reference but instead for the decor’s prominent coloring.

I have nothing but positive things to say about our cottage. When we arrived they left the key for us in a lock box and responded to our text immediately. When we went inside we were greeted with two appropriately “themed” bottles of wine along with instructions, a wifi password and a sweet note informing us that they had freshly baked muffins, homemade granola, yogurt, orange juice and milk for our use.

The house accommodates up to six people but we were quite comfortable with four of us. Though we could have squeezed another couple, having only one bathroom may have made that a little difficult. Everything was clean and the decoration was impeccable. It was designed by a local decorator who seems to be somewhat of a legend, Connie Cross. If I could, I would buy this place fully furnished and call it a day!

Here are a few photos of our wonderful stay!

Here is the living room:

Where to Stay in the North Fork

Here is the master bedroom:

Where to stay cutchogue five star

Here is another shot of the master from the other side of the room.

Where to Stay in North Fork Long island

Here is the larger of the other bed rooms:

North Fork Long Island Luxury Travel

Here is the smaller of the other two bedrooms

Where to Stay Luxury Long Island

We carried in for dinner. Tres romantic, oui?

Did I mention there is a fire pit? Luckily we had two intelligent men who built us a fire! The women instead chose to drink wine and kick our feet up for once!

The bathroom was tidy, but on the small side. You may not be too comfortable if you’re a large person–especially in the shower. They did have toothpaste in case you forgot it! I didn’t see toiletries though so do remember to bring your own.

There was also a great laundry room with very new machines! If you live in the city you know how excited you get to have access to machines in your living space–especially ones that run without quarters!

Ooh and the backyard had plenty of seating around the fire pit but also there were several lounge chairs. The swing was my favorite though!

The house has A/C and heat and everything modern you could want. The kitchen also is equipped with dishes and anything to cook that you might possibly need. And I was just obsessed with all of the glassware, it was like they cut the kitchen right out of a catalog of perfect kitchens. I’m not sure if this picture does the kitchen justice but the open space was fab. Just loved it! Oh and they had a mason jar filled with hershey kisses! Yum!

Ohh and here is the fabulous farewell breakfast we had at the house with the goodies they left us. Bon voyage, indeed! How adorable are these place mats!? And the homemade granola was insane!

What to Do

When you’re out in the North Fork, it’s mandatory that you visit many, many wineries, farms and seafood restaurants. While the North Fork isn’t quite up to Napa standards quite yet, if you know what vineyards to go to, you can actually find some very lovely wines. But more than the wine, the atmosphere is what a trip to the North Fork is all about. Sitting outside, enjoying live music and just taking in the views. Here are a few of my the best wineries in the North Fork:

Kontekosta Vineyard is absolutely stunning. While the wine was good, this place had the most gorgeous atmosphere. They also stock cheese from local farms, which made an absolutely delicious breakfast! You must try the Goat Cheese from Catapano here, it’s delectable! Yes, we stopped here at noon! haha. Kontekosta is on the water and the views of the Sound are stunning. Check this out!

Best Things to See North Fork

McCall Winery is quaint and peaceful. They have a killer Pinot Noir. We didn’t visit on this last trip out since they were closed but had been there on a previous trip.

Shinn Vineyards is very laid back and has a really cute atmosphere. Their Merlot was incredible here. It’s a biodynamic vineyard (still haven’t figured out what that means) but it was gorgeous and the wine here was our favorite that we had.

Sherwood House Vineyards are also lovely and worth a visit.

Sparkling Pointe serves up only sparkling varietals and while they’re pretty good, the atmosphere here is one of the most beautiful in all of the NoFo. Being here makes me feel like I’m in Napa or Sonoma–though I’ve never been! Crazy, I know. But it’s truly just a gorgeous vineyard.

Oh, and word to the wise–Vineyard 48–it’s the bad boy of all long island vineyards. The locals hate it! I had come here in the past and had a great time. It’s definitely the biggest party vineyard in the North Fork, which means lots of drunken, loud, idiots and very few clean bathrooms. We came here thinking it would be a funny, crazy scene. I guess we’re too old because watching girls chug wine out of buckets just wasn’t what we were looking for. However, if you are in town for a bachelor or bachelorette party, this is probably where you’ll want to be if you’re hoping to find other like-minded, or like-out-of-your-minded people.

Where to Eat

The North Fork seems to be undergoing somewhat of a foodie revolution right now. It seems as though many New York City chefs bitten by the farm-to-table craze, in an effort to get closer to the farm, have moved out to the North Fork to start their own restaurants. We had such amazing food when we visited Greenport, Mattituck and Cutchogue (all within about 20 minutes of each other). Here are some of my favorites and then a few picks that a local foodie recommended!


Harbes Family Farm has the best corn in the world.  You can try some here or pick it up and grill it up at home. They also have a special fall festival going on. There are also locations in Riverhead and Jamesport. You can’t come to the North Fork and not come here.

Love Lane Kitchen has good food and a cute atmosphere. Locals think its overpriced and a tad too touristy which it is, but hey, that’s what you’re here for! Locals still love it though!
Amoretti Brothers Cafe is a great deli. Perfect for picking up picnic supplies. You can eat here but there isn’t any waitress service.
For amazing ice cream check out Magic Fountain, which is family-owned and serves up homemade ice cream churned up on site!


Greenport is the cutest little seaside town. Ever. It’s right on the water. In fact, the LIRR has a stop here and then it’s like a 2 minute walk into the main part of town, which is filled with amazing shops and restaurants.
They have great oysters here (or so I’m told. I’m not the biggest fan but everyone I was with slurped a whole bunch down!)
For an amazing brunch, lunch or dinner check out Noah’s.  The lobster rolls, lobster macaroni and cheese and sashimi were incredible. Also, the Bloody Mary with poached shrimp was fab!
The Frisky Oyster serves up fab seafood.
Southold Fish Market just re-did their space and it’s supposed to be REALLY nice. Next time!
For drinks along the water with a gorgeous view and great oysters, check out the Blue Canoe Oyster Bar.

Oh! And there is also a Ralph’s Italian ices in town! My favorite!  And for amazing organic soaps, oils, and candles plus gorgeous housewares be sure to visit the Weathered Barn. I’m obsessed with this store! Fabulous place to pick up some cute gifts!


Michaelangelo of Cutchogue is an adorable Italian/Pizza restaurant. We just took the salad pizza to-go, which we were told is the Best. Salad. Pizza. Ever. And it’s the truth! It’s incredible.
Braun’s Fish market is fantastic! You can pick up the freshest, expertly prepared seafood, or eat in if you’d like. You can get anything from whole lobsters to grilled fish to creative wraps like buffalo shrimp.
Best restaurant north fork seafood


Sang Lee Farm – has incredible organic produce. They specialize in Asian greens, vegetables, herbs, flowers and dressings. Their motto is fresh-Lee cut. How adorable.


Briermere Farms‘ pies are where it’s at! Apple, peach, raspberry, key lime, chocolate cream–you name it! Pick one up. Thank me later!
The North Fork is an amazing weekend escape or summer escape from the grind of the city. We had the best time ever! Ohh and if biking is your thing you can rent bikes at Greenport Bike Rental or Vintage Bicycle Tours. Whatever you do though–remember not to drink and drive!
A special thank you to Jessica K for her amazing suggestions, which helped us create a fabulous weekend and this amazing itinerary!
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