The Village of Greenport was settled by colonists from Connecticut around 1640. Back in colonial days, the village of Greenport was known as Stirling; for the British Earl who who laid a King’s claim to most of Eastern Long Island and 
New England.. Its port was coined “Winter Harbor” as it was accessible to ships even when the Town Harbor was frozen over. Greenport’s main road was laid out in 1827 and was incorporated in 1838. Greenport was famous as a whaling center in addition to its fishing and ship building industries.
old opera houseDuring the Revolutionary War a wharf was located on the west side of Stirling Creek and was the place where vessels tied up and discharged and loaded cargo for ports in the Western Hemisphere. Another wharf, on Central Avenue was completed in 1838 and not a moment too soon as shipments of sugar, molasses and rum from the West Indies were in high demand. Because of these wharves and Greenports strategic location, the village became a key 
whaling port with over two dozen whaling ships which made in excess of one hundred expeditions between 1790s and the Civil War.old railroad scene
The name of the village was changed again to Greenhill during this time and finally renamed Greenport when the village was incorporated in 1838.
Greenport celebrated the arrival of the first train on July 25, 1844 via the Long Island Rail Road. Later, Greenport became the key port of call for the steam side-wheelers leaving New York and arriving in Greenport with connections to Block Island and New London.
From the early 1800’s through WWII over 550 ships were built and launched in Greenport. Some of the more well-known shipyards were the Hiram Bishop, Matthew & Fordham, and Smith & Terry which is the current location of Greenport Yacht & Shipbuilding.
During World War I the Greenport Basin & Construction Company built vessels for the Russian Navy, as well as the US Navy and in World War II the same shipyard built mine sweepers and landing craft as well as tug boats.
After the turn of the century, up until the early 1960’s, oystering was a major business in Greenport. At one time there were fourteen oyster processing companies situated in Greenport.
During the prohibition era of the late 1920’s and early ’30’s, “rum running” became a major source of income for the Village of Greenport. Greenport’s protected harbor, excellent docking facilities, shipyards and repair capabilities made it a suitable place for this type of activity. Part of the village even became known as “Rum Row.”
old north ferryDuring World War II Greenport was one of the headquarters for the offshore Picket Patrol. In the early days of 1942 and 1943, the United States Navy had little capability to patrol our coasts for German submarines. The Picket Patrol consisted of donated wooden sailboats which patrolled way off shore and in many cases under hazardous conditions.