How To Vacation In The North Fork, From Someone Who Lives There Year Round

July 13, 2016 by MichelleMadhok
shefinds | Style

I’ve been procrastinating writing this article. The SHEfinds editors asked me to write about what they know is my favorite place on earth, the North Fork of Long Island, and I’ve been dragging my feet. Mainly because as much as I’m happy to share my finds with 2M people a month (hence the site), I’m worried about 2M people descending upon my small patch of paradise.

This is a place where my husband and I go every weekend with our dog to rest and recharge after the long, crazy week in Manhattan. Every Friday we grind our way out of midtown, fighting road rage and breathing exhaust on the 495 for about 2 hours (it can take up to 5 in the summer!). For those that don’t know, the end of Long Island splits into a V–to the south is the glitzy Hamptons you’ve seen on “Revenge” and the RHONY, that’s where the New York “fancy” people spend their summers. The North Fork is not that.  This is a region focused on food, wine and breathtaking sunsets. The vistas are grapevines, farmland and still bodies of water. When we hit exit 71 and start heading North, leaving the Hamptons traffic behind us, we breathe a collective sigh of relief. It is the best moment of my week.

While there are great things about this area being discovered by more people–more restaurants, cute shops, new friends–there’s also the agritourist traffic that comes with. As an example, the small winery I used to love now has a hostess at the door giving wait times. The wooded vacant lot across from my house just went up for sale for an obscene price, and a lifeguard recently kicked my dog off a normally-deserted beach (and his favorite!). There are some obvious downsides to sharing my North Fork with the world (I’m very protective of this place)–but it is worth sharing, so here goes. Just please don’t all come at once!

Here are the recommendations I share with my closest friend (and now you!) when they are coming to visit for just a couple days:

Where to stay:

You have a choice  – do you want to be in nature/vineyards or a cute small town?

If the former, you can look in to aribnb’s in Southold–but thanks to a new short term rental law in the area, you can only do airbnb’s for 2 weeks or longer. (Don’t worry–you’re not missing much, one of my friends said her AirBnB had bats in it!)

If don’t plan on staying for that long, or want a bit more service, check out the luxe and historic Jedediah Hawkins Inn which also has an amazing restaurant attached. Just last week @Gumbydog and I visited their chickens after a fabulous brunch.

If you prefer the small town vibe definitely stay in Greenport.  American Beech is a new cool-vibe  hotel/restaurant right in the middle of town.  Other good options are the retro Greenporter Hotel and the Harbour Front Inn (on the water natch).  The great thing about staying in Greenport is that you can take the LIRR or the Hampton Jitney directly to Greenport and walk to your hotel.  

Where to eat:

If you’re looking for me on a Saturday afternoon more often than not I’ll be at my happy place, First and South eating a “Really Good Burger” with Siracha Mayo.  The food is local and the staff is crazy friendly.  Make sure to say “hi” to boss lady and owner Sarah Phillips Loth who is a good friend of mine and a Greenport treasure.

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Happy birthday MP! #nofo #northfork

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Be sure to also visit these restaurants in Greenport: American Beech, Noah’s and for dinner The Frisky Oyster.

Other regular dining haunts of mine:

Every Friday night I’m at Amano – both because it’s close to my house and because it’s Italian comfort food  made with local ingredients.  Something I need after sitting in traffic for 2 hours.

Sunday lunch is at the crazy cute Love Lane Kitchen. They have the best lobster roll. Unfortunately this place has been “discovered” by daytrippers (I know I’m not helping things by listing them here) so there’s always a wait to be seated.  Fear not though because across the street is the tasting room for Roanoke Vineyards – one of the best wines produced on the North Fork so treat yourself to some vino while you wait.  

Do not miss Magic Fountain for Ice Cream. They make tons of flavors with mouth feel–like strawberry shortcake and red velvet that are to die for. They also make ice cream treats for dogs.

For eating on the water visit The Old Mill in Mattituck.  They are known for very fresh seafood. I once saw that them storing their lobsters in the Mattituck inlet off their deck.  


The best thing to do is to choose 2-3 wineries that are somewhat near each other so you aren’t spending the entire time in the car.  Someone needs to stay relatively sober so I endorse the idea of sharing tastings so the driver can have a sip without getting blotto.

Here are some pairings when choosing where to go:

Mattituck Area:

Shinn, Lieb, Macari = solid picks mostly free from bachelorette parties.

Southold Area:

McCall Vineyards makes the most award winning wines on the North Fork.  Visit them on Friday’s for burger night made from their own grass fed Charolais beef.

Croteaux  only if you like Rose because that’s all they make! This place is the most insta-worthy vineyard. They have a beautiful provencal garden, but with the surge in Rose love, lately there’s been a long wait to get in so I’ve stopped going.  Go on a weekday if possible.

Also nearby and solid options for when Croteaux denies you: Corey Creek and Bedell.


5 minutes from downtown Greenport is Kontokosta Winery which is by far the most stunning of all the wineries on the North Fork.  It’s a large modern barn set on a bluff over the sound. They make Viognier which is one of my favorite grapes. My only dislike is that they don’t allow dogs and I have issues with dog hating places.

Overall there are two types of wineries – chill ones that don’t allow limos and focus on the wines or agritainment wineries that are all about big groups and a party atmosphere.  I’m more about the former so don’t try to show up at any of the above in a limo.

Make sure to stop along the route for some amazing photos of old tractors, fields of sunflowers and rosy sunsets.  The North Fork is all about slowing down and being present.  To get an idea of the sites jump on instagram and search #nofo #northfork and #northforker.

You can follow me and @gumbydog on Instagram to see more of our adventures, but remember I wrote this just for you.  Don’t tell anyone about our secret place.

P.S. There’s some shopping to be had too. On the way out of town hit Tanger Outlet Riverhead. I’ve scored serious deals at Barneys, Off 5th, Vince and Rag and Bone outlets.


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