If you are looking for a great spot on Long Island sans the drama and excessiveness of the Hamptons … Greenport is the place for you! Charming and steeped in history, this small town makes for a great weekend getaway.

In the mid 1600s, a group of colonists from New Haven, Connecticut crossed Long Island Sound and settled in the township of Southold, which includes what is now the Village of Greenport. Because of its deep and protected harbor, Greenport became a major whaling port between 1795 and 1859 and enjoyed a bustling shipbuilding industry as well. By the mid 1800s, the menhaden fishing industry was in full swing and employed thousands of people. The Long Island Railroad arrived in 1844 and was a driving force in the development of Greenport and the North Fork as local farmers used the railroad to ship their harvest to markets. Greenport became a huge oystering center during the first half of the 20th century and at one time there were over a dozen oyster processing plants in town. As the oyster industry began to shrink, the Village turned its attention towards tourism and has developed into a vibrant destination for visitors from all over the world. In 2011, Forbes magazine named Greenport one of the prettiest towns in the United States. Check out some of our favorite spots in Greenport…

Places to Eat:

1943 Pizza Bar – 308 Main Street (in Stirling Square)
Located in Stirling Square on Main Street, 1943 Pizza Bar offers delicious brick oven pizza with a variety of toppings available. Innovative combinations and outdoor seating make for a delicious and charming dinner!

Little Creek Oyster Farm & Market – 37 Front Street, Greenport, NY 11944
The little shack in the heart of Greenport Village has seen a fair share of time and tides. It began life as the wheelhouse of a great whaling ship until that fishery faded into history. It was cut off and brought ashore in 1880.
Now it houses Little Creek Oyster Farm Market where you can shuck your own oysters (instructions and tools included). The shop also provides picnic supplies, saltwater flies, handmade tackle and other unique durable goods will available to round out the offerings. Due to the inclusive approach, other small growers and farmers will have the opportunity to showcase the fruits of their labor as well.

The Frisky Oyster – 27 Front Street Greenport, NY 11944

Places to Shop:

Lido – 119 Main Street, Greenport, NY 11944
Hand-selected jewelry, home furnishings and one-of-a-kind pieces from artisans around the world, as well as the LIDO capsule resort wear collection.


Local Knit – 15 Front Street Greenport, NY 11944
For the “not your average” souvenier, try Local Knit. They create shirts featuring local mainstays in distinct towns across the country. From waterside watering holes to salty fishing lodges, these places have real stories and they help build communities of uncommon character.

local knit

Made in New York – 413 Main Street, Greenport, NY 11944
At Made in New York they strive to expand the availability of locally grown, produced & manufactured goods. They have created a retail environment where you can easily access fresh gourmet food, fabulous fiber-art items, and fantastic dry goods. ALL which have been produced in the great State of New York. We loved the waxed canvas totes, perfect for holding all your local treasures!

The Times Vintage
– 429 Main Street, Greenport 11944
Housed in the old Suffolk Times newspaper building, The Times Vintage sells a collection of art, fashion, and furnishings.


Places to Stay:

The Harborfront Inn – 209 Front Street, Greenport, NY 11944
In the heart of the historic seaside Village of Greenport on Long Island’s North Fork, the Harborfront Inn epitomizes understated luxury and comfort. Designed as a retreat for discerning guests who wish to immerse themselves in the unique rural culture of the North Fork while enjoying the finest of amenities, the Harborfront Inn offers the best of all worlds.

harbor front inn

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