You’re going for a weekend to avoid the Hamptons scene and enjoy some oysters, sunshine and a low-key vibe.
Hampton Jitney or LIRR Both are easy options and drop off in the same location in Greenport Village.
Rent a Car It’s nice to explore the areas outside of Greenport, though you don’t really need it for just a weekend.
Rent Bikes It’s the kind of town you’re going to want to roam around on a bike, especially through some of the tiny, windy streets.
good to know
Dinner Book dinner reservations ahead as a lot of them do fill up even though it’s a small town.
Ferries If you plan on driving to Shelter Island, book a spot on the ferry ahead of time. Bikes and people can walk on easily and pay on board.
Best Time to Visit The summer months are prime time but fall is also really beautiful and quiet. Spring can be iffy with the weather. Keep in mind that it’s a summer destination so a lot of places are seasonal. Call ahead if you’re traveling off season.
eats & drinks
Bruce & Son Upscale diner with fantastic sandwiches and healthy plates that’s good for lunch or brunch.
Little Creek Oysters Serving fresh oysters with picnic tables outside, you can order them shucked or do it yourself with tools and a quick tutorial from the staff. They serve local Greenport Brewery beers, and it’s pretty much the ideal place to go during the summer. Look for the Bait & Tackle sign on the pier just before Claudio’s.
Noah’s Well-executed seafood best characterizes Noah’s. The restaurant is upscale casual, making it perfect for families or a nicer group dinner.
Port Waterfront Bar & Grill With outdoor and indoor seating and an endearing nautical theme set by the marina, this casual restaurant serves good lobster rolls, seafood items and a solid brunch. Service can be hit or miss.
First and South While the setting is beautiful with an outdoor patio and strings of lights, the menu often reads better than the execution for both drinks and food.
Barba Bianca From the owner of NYC’s peasant comes this upscale Italian restaurant with outdoor seating. Good to go if you want NYC quality food when on vacation.
1943 Pizza Bar In the same area as American Beech, this pizza spot is ideal for a grab-and-go meal or take out. Is it as good as NYC pizza? Highly debatable but probably the best out there.
Lunch Truck from North Fork Table & Inn In the summer, a truck from this famed and high end restaurant serves casual food like lobster rolls, pulled pork sandwiches and hot dogs. Obviously, everything is executed well because, well, it’s them. (In Southold)
The North Fork Table & Inn A residence and fine dining restaurant that offers brunch, it will be fancier than the rest of the eating options out there but it’s worth the trek to enjoy the quality of food, visit the site or celebrate a special occasion.
The Market Go here for morning green juice, pretty good prepared foods and almost any health-related product you can think of in case you forget your goods at home.
Sandpiper Old school ice cream with a bare-boned, almost run down decor, you feel a bit like you’re transported to the ‘70s when you order, which is a nice feeling.
Greenport Brewery With a small tasting room located in Greenport, the brewery opened a much larger venue a little farther south that offers live music. Stop by the upstairs tasting room for flights or a pint. It offers a quiet, casual setting with old kegs covered with a seat cushion and good for rainy days.
Brix & Rye A speakeasy type bar around the corner from American Beech, it’s located downstairs and offers craft cocktail bar in a dimly lit setting that’s akin to an upscale East Village bar. There are small seating areas but not ideal for groups.
American Beech With decor that makes you feel like you’re in Montauk, American Beech serves delicious cocktails with an indoor and outdoor bar area as well as large group seating. They also have a full restaurant inside.
Claudio’s Clam Bar If you’re looking to reclaim your youth and dance to throwbacks, definitely visit this bar on the pier. It’ll be crowded, filled with bachelor or bachelorette parties and is pretty fun, if you’re in the mood.
see & do
Kontokosta A beautiful winery that’s within walking and biking distance of the center of town. It’s set by the ocean with picnic tables so you can enjoy cheese and meat plates and flights of wine with gorgeous views around you. Live music is offered on some days, make sure to check the schedule. There are other wineries within a driving distance, but this is a good one if you don’t want to deal with driving or hiring a driver.
Sunset Beach/Shelter Island Located on Shelter Island, this beach restaurant/bar located in a hotel is a scene. Think Miami meets Ibiza with some Jersey Shore and Long Island flare mixed in. It makes for incredible people watching. Book a lunch reservation as it fills up and spend the day drinking and eating while you people watch. Crescent beach is across from it and open to the public with paddle boarding available. The rest of Shelter Island is quaint and adorable with some massive houses.
Orient Point At the tip of the island, the views are beautiful and worth visiting if you have a car or are up for a longer bike ride.
Rocky Point Beach Bike to this tiny, hidden beach overlooking the Long Island sound in East Marion. While it’s a pebble beach, there are rocks for climbing, space for swimming and, best of all, very few people. Cars will need a permit to park. The road, Rocky Point Road, is across from a lavender farm, that’s also worth visiting.
Seb’s Farm Stand Located in East Marion, a quick drive north of Greenport, the stand has good quality seasonal produce.
Lavender by the Bay Pick up your year’s supply of lavender here and check out the fields. It’s right near Seb’s, so you can get all your goods in one place.
Southold Fish Market Fresh, local fish that you can grill at home with a little lemon and fresh herbs.
North Fork Yoga Shala Housed in a beautiful space right near the center of the village, the studio offers great yoga classes as well as wellness treatments like acupuncture and massage. You’re on vacation, right?
American Beech With no dedicated hotel staff, this shabby chic beach cottage offers two rooms above the restaurant, which, as you can probably guess, lead it to be somewhat noisy. It’s ideal if you want a beautiful, clean setting and plan on partying during your stay. $$$
Soundview Outside of Greenport village itself (a short bike ride away), this property is located on the water. Rooms are bright, airy with large windows overlooking the water. It has a chic, cabin-by-the-sea feeling to it. $$$
Cliffside Resort Condos Overlooking the sound, these condos provide a kitchen, two bedrooms/bathrooms and living room with a private balcony. Some are better decorated than others, but it’s good for groups. Don’t expect luxury accommodations or to be blown away, but if you’re looking for somewhere for a group to stay, have access to the beach and be a short drive or 10-minute bike ride to town, then you’ve found your spot. $$-$$$
The Chequit Technically on Shelter Island, this property is what you think of when you picture a cute inn, recently renovated with tip top shabby chic decor: A white-washed porch with comfortable chairs, bright rooms with pink and yellow accents, deep soaking tubs and lots of light. The ferries run so frequently to Greenport that you can easily go for dinner and back.
AirBnB Finding somewhere within walking or biking distance of the town might be your best bet if you’re in a larger group or looking to take advantage of the farm stands and fish markets near by. $$-$$$
Sag Harbor If you have a car, you can take the ferry to Shelter Island then cross over to Sag Harbor, which doesn’t take long as Shelter Island is really small. This might be a good thing if you’re spending longer than a few nights in Greenport.
Who Visits The town is split between families who are enjoying a wonderful escape from the city and bachelor/bachelorette parties. The latter tends to do all-day wine drinking tours and hit Claudio’s at night.
A Tiny Village This little gem of a town and most of the North Fork is growing more and more popular as people are escaping the Hamptons, which is understandable as it is beautiful, quiet and filled with good food.