"Picturesque Village of Greenport" Greenport by TooTallFinn24

Hidden on the north half of the outer tip of Long Island, the Village of Greenport is like stepping into another world. Quiet, dignified but not overly pretentious visiting Greenport on my own on a mid September afternoon was a sure delight.
Approaching the village from the east you drive through a combination of vineyard fields with frequent breaks to relaxing views of marshes or the Long Island Sound.

Visiting the village of Greenport was so much more relaxing than visiting the southern tip of the Hamptons with all of its traffic and ostentatious homes. It is easy to maneuver around the village. I first walked around some of the outer streets around the Greek Orthodox Church. Many beautiful homes and summer cottages. Further in town the area north of Main Street contains the village library and some beautiful old homes.

The business area is crammed full of antique shops, restaurants, a museum and some interesting shops. There are several good places to eat. My favorite was Claudios right on the water.

Interesting Old Buildings on Main Street

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. Southold is just to the west of Greenport. Over the course of its history, Greenport has been known by several different names including Winter Harbor, Stirling, and Green Hill. At a public meeting in 1831, the name Greenport was officially adopted.

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.

Today Greenport is a fascinating plethora of small shops, beautiful homes and cottages, a great waterfront, and a grid system of streets that is great fun to walk around

Source: Greenport: You Don't Have to Go Far To Get Away, 2012

• Pros:Picturesque, Relaxing, Great Waterfront
• Cons:None
• In a nutshell:One of the Prettiest Villages in New York