Monday, July 10, 2017


Over the 4th of July weekend I took a petite trip to the North Fork of Long Island—to the sweet little town of Greenport. I wasn't really sure what to expect, but what my friends and I experienced was a food-fueled, relaxing and mostly oyster-centric summer getaway.

Without the crowds of Montauk or The Hamptons and with tons of local wineries nearby, Greenport feels a little bit like a secret. You can get to the beach on Shelter Island by hopping on a ferry and you can do some serious mingling and cocktailing at bars like Brix & Rye and American Beech. A small town that has it all? Maybe. I'll let you decide...


// EAT & DRINK //

STERLINGTON DELI: This family-run deli is the real-deal. Head here in the morning and order a truly delicious, no-frills bacon, egg and cheese on a roll. You will not regret it. This is also a great place to pick up sandwiches before a day on Shelter Island or for a picnic. Just saying.

BRUCE & SON: This was the first spot we tried out upon arriving in Greenport on Friday afternoon. It's only open for breakfast and lunch and they do not have a liquor license, just FYI. What they do have are several super-delicious homemade lemonades and really great sandwiches and brunch options. 

GREENPORT HARBOR BREWING: Ex boyfriends and current male friends have turned me into a very minor beer nerd. (See Jerry's fall and spring beer guides for proof!) Now I absolutely love swinging through local breweries when I'm traveling. The Greenport Harbor Brewing tasting room is low-key and simple and their beers are great. It's the perfect place to regroup mid-day, especially if the weather is less than stellar. 

1943 PIZZA BAR: I wanted to include this place because even though we didn't go, I read about it in the local magazines and when we walked by one night on our way to American Beech, it was absolutely packed full of people eating very, very authentic and delicious-looking pizzas. It's on my radar for my next trip!

LITTLE CREEK OYSTER FARM & MARKET: Okay so this spot might have been my favorite of the whole weekend. Tucked onto a little patch between a couple of parking lots right on the harbor, they "let you" shuck your own oysters as you sit at shared picnic tables under colorful umbrellas. (Spoiler alert: Shucking your own oysters is really hard.) The beers are good, the oysters are outstanding and the low-key, friendly vibe of this place encompasses what Greenport is all about. 

AMERICAN BEECH: On the fancier end of the spectrum in Greenport is American Beech—a restaurant, outdoor bar and teeny-tiny hotel. The outdoor bar is built around, you guessed it, a big beautiful Beech tree, and is lit up with tons of strings of lights and lanterns. Make a reservation to have a decadent dinner here or stop by after dinner to sit by the outdoor fire and have a Moscow Mule and take in the lively scene.

THE FRISKY OYSTER: Another fancy and very busy spot in town, The Frisky Oyster has everything going for it. (Make a reservation if you want to sit for dinner.) We decided to stop in for a cocktail and appetizers one night, which was perfect. We ordered oysters two ways and sat at the bar with tequila cocktails—an ideal start to a summer night if you ask me.

BRIX & RYE: This underground bar is a bit of a speakeasy—and they serve up some seriously delicious cocktails. The vibe feels very Brooklyn, but the crowd is a bit of a mixed bag. Once the sun has set and you find yourself in the mood to settle into a dark corner with a frozen drink called "Intro to Aperol" this is the place to go.

// WHAT TO DO //

LAVENDER BY THE BAY: Do you like scenic places that smell better than almost anything? Are you not that afraid of bees? Then you should definitely visit Lavender by the Bay—a beautiful lavender farm where you can wander the fields taking copious Instagrams, sitting in purple Adirondack chairs and doing your best to act chill around a lot of very busy bees. Be sure to swing through the farm stand after to stock up on all kinds of amazing-smelling, make-you-calm tchotchkes like eyemasks, lotions and embroidered sachets, too.

SHELTER ISLAND (AND SUNSET BEACH): Shelter Island is one of those beautiful, low-key hideaway spots on Long Island that nobody wants you to know about. So, read this but don't tell anyone, okay? The beaches are scenic and the water is warmer and way more mellow than the rollicking Atlantic you have to tussle with in The Hamptons.

Sunset Beach (a gorgeous bar, restaurant and hotel situated right on the beach) on a Sunday night, however, is not low-key nor is it hidden. It is wild and totally overrun and really fun. The "scene" must truly be seen to be believed. Plan to spend about $18 per drink (seriously) and unless you're truly flush with cash, don't bother with a sit-down dinner here.

The better plan is to take the ferry over in the afternoon and set up shop on the beach with a picnic and a cooler. Dance and have a drink or two in the evening, watch the sunset and then head back to home base.

KONTAKOSTA WINERY: We didn't end up fitting the winery into our weekend, but my friends had been before and highly recommend it for you guys. (What? You thought I wouldn't ask?) Their tasting room is open most days until about 6 p.m. and you can take your wine out into the grassy field that overlooks a bluff on the ocean which sounds like the most enjoyable way to drink a local sauvignon blanc.

RENT A BICYCLE AND EXPLORE: Another thing I'd do on my next trip is rent a bike so we could ride around and explore a bit more. You can get a full-day rental for about $25 from Dan's, making it an affordable and scenic way to experience all of the above activities.


THE GREENPORTER HOTEL: We stayed at this fun little motel and couldn't have enjoyed ourselves more. The location is ideal—it's just on the edge of the busy part of town; a quick walk down Front Street will put you in the heart of the action. (Not to mention it's a very short walk from the train station in case you're carrying a heavy bag.) They also have a pool, which was key for starting and ending our days in a totally relaxed mode. We'd wake up and enjoy the delightful (price-inclusive) continental breakfast on the porch and then spend an hour or so reading our books by the pool before venturing out for the day.

AMERICAN BEECH: The hotspot I mentioned above has five (gorgeously appointed) suites for guests and also supplies bicycles. They're located in the heart of town and the bar is lively until the later hours, so keep that in mind if you decide to book.

THE GALLERY HOTEL: We popped in to check out this little Main Street hotel on a whim. They have just nine rooms and a beautiful back garden. (It reminds me a lot of the Maidstone in East Hampton in terms of size and eclectic design.)


THE LIRR: One of the most appealing things about a trip to Greenport is that you don't need a car. The town is tiny, and the train station is a short walk from the harbor area, restaurants and most of the hotels, too. My hot tip for train travel out from New York is to download the MTA eTix and TrainTime apps before you go. You can book and pay for your train tickets in advance, which makes the whole Penn Station thing way less stressful.

*There are supposed to be some dramatic changes to Amtrak services through the month of July, just FYI you might want to plan ahead for that!

HAMPTON JITNEY: If you can travel during off-peak traffic hours, the Hamptons Jitney is a delightful way to get to and from Greenport. The drop-off is in the train station parking lot, which is convenient and your ticket (usually about $20 if you book in advance) includes wifi, water and snacks!


Greenport is really casual. Like, really casual. You can pack light and plan to wear shorts, tops and sandals pretty much everywhere. I'd bring sneakers for bike riding and a sun dress or two for dinner in town, and just a few warmer pieces in case the breeze picks up like it did when we were there. (White jeans and a men's summer sweater should do the trick!) Shop a few ideas to get you started below!

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