Greenport Getaway: Getting to Know Kontokosta Winery

Look to the North Fork of Long Island and you’ll find an escape that’s far removed from the hustle and bustle of the busy city. Here, you’ll enjoy a serene retreat while you get to know one of the best North Fork wineries, Kontokosta Winery.

Plan the perfect weekend trip with our insider’s guide to Long Island’s favorite winery.

Day 1


Whether you’re coming by plane, train, or car, you’ll feel relaxed upon your arrival to Long Island’s bucolic North Fork. Before starting a weekend of wine tasting, settle in at The Harborfront Inn. Just a mile down the road from Kontokosta Winery, you’ll enjoy the luxurious, waterfront accommodations. After check in, take a walk through our charming village and take advantage of the many offerings of our local shops. Don’t forget to head out to the docks and breathe in the sea air while admiring the views of Shelter Island and the harbor.


While in Greenport, don’t miss out on fine dining. Treat yourself to dinner at one of Greenport’s favorite restaurants within walking distance of the inn. Indulge in fresh, locally-sourced specialties at Noah’s, the Frisky Oyster, or newcomer the Green Hill Kitchen. Afterwards, enjoy the cozy atmosphere and delicious, handcrafted cocktails from Brix and Rye.

Day 2


Wake up to the smell of a fresh, complimentary continental breakfast and all-day coffee service at The Harborfront Inn. Take a stroll along the harbor and be sure to stop into Aldo’s. Grab a cappuccino or latte and a freshly-made biscotti before embarking on day two of your weekend in Greenport.


On your last afternoon in Greenport, head over to Kontokosta Winery. You’ll arrive via a long driveway surrounded by rows of beautiful vines. From there, you’ll make your way to the tasting room where you’ll enjoy a curated selection of our exceptional wines. Sip and sample from the comfort of the tasting room or head outdoors to enjoy the view from the bluestone terraces or the bluff overlooking the Long Island Sound. Don’t forget to pair your wine with a delectable selection of local cheese, charcuterie, breads, and other sweet and savory snacks. All of our food can be enjoyed from one of the many picnic tables that offer sweeping views of the water and Connecticut.


End your perfect weekend getaway with one last Greenport sunset cast over the waterfront. Grab a casual dinner at Lucharitos or Stirling Sake and feel rested before retreating to one of our cozy rooms or suites.

Still have questions about planning your weekend at Kontokosta Winery? Contact us for recommendations to make the most of your North Fork weekend getaway.