Development as a community was slow. In the years following the Revolution, Sterling Street evolved as a southern arm of King?s Highway along the west side of Sterling Creek. (Note that the spelling of Sterling changed over time.) It proved to be a busy thoroughfare with a small cluster of houses and an inn, long since relocated to Orient, that Washington was reputed to have visited. Throughout these early years, the Sterling Street Wharf was an important way for exotic goods form the Caribbean and South America.
Main Street, the principal commercial street, was cut through in 1827, and the Green Hill Wharf was constructed at its lower end. Another wharf, on Central Avenue, completed in 1838, was in high demand with shipments of sugar, molasses and rum from the West Indies. Because of these wharves, the village became a key whaling port with over two dozen whaling ships which made over one hundred voyages between 1790s and the Civil War.

Since there were other settlements named after Lord Stirling, in a public meeting held on June 23, 1831, it was decided to call the village ?Green Port?. By the time the Village of Greenport was incorporated in 1838, it was a place of considerable commerce. Its deep-water harbor accommodated large ships, and many whaling and fishing vessels were outfitted here. Boat building became an industry, and numerous shops accommodated the growing maritime industry.

The Village of Greenport, part of Southold Town, was settled by colonists from New Haven, Connecticut around 1640.? The first recorded lands belonged to the Young's family on the west side of Stirling Creek.? Before the Revolutionary War, the village was referred to as Winter Harbor and later Stirling after Lord Stirling, George Washington's general who laid a King's claim to most of Eastern Long Island.
At the time of 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 North and South America and the Caribbean.? The name of the village was changed again to Greenhill and finally renamed Greenport when the village was incorporated in 1838.

Greenport became a major whaling port with twenty-four whaling ships making a total of 103 voyages between 1795 to 1859 to the whaling grounds in the North Atlantic, South Atlantic, and Pacific.
From the early 1800's through World War II over 550 ships were built and launched in Greenport.? Some of the more famous shipyards were the Hiram Bishop, Matthew & Fordham, Ketchum & Smith, Smith & Berrian which later became Smith & Terry, the present 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.? Also famous was the Beebe McLellan Lifesaving Surf Boat designed and built in Greenport, along with the Gaffga Marine Engine.

In 1844 the Long Island Railroad established a link in Greenport as part of the New York to Boston connection.? Steam side-wheel ferries transported people and freight from Greenport to Stonington, Connecticut, where they made connections with the Boston trains. Later, Greenport became the major port of call for the steam side-wheelers leaving New York and arriving in Greenport with connections to Block Island and New London.

The menhaden fishing industry had a major impact on Greenport in the mid-1800's to the mid-1900's.? The fish was harvested for its oil but also for animal foods and fertilizer.? Many older Greenporters still remember the odor (unpleasant to most) from the "Bunker" processing operation and the "Bunker" boats.
After the turn of the century, up until the early 1960's, oystering was a major industry in Greenport.? In fact, at one time there were fourteen oyster processing companies located here, with the dockside values of oysters often running as high as two million per year.

During the late 1920's and early '30's, with prohibition in full swing, "rum running" became a major income producing activity for the Village of Greenport.? This was due to Greenport's protected harbor, excellent docking facilities, shipyards and repair capabilities.? Part of the village even became known as "Rum Row."

During 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.

Greenport also has a connection to the America's Cup.? Captain George Monsell sailed the majestic J's to victory in the "Enterprise" (1930), the "Rainbow" (1934) and the "Ranger" in 1937.

To learn more about Greenport's maritime history, visit the East End Seaport Museum, the William Floyd Memorial Library, the Long Island Railroad Museum and the Stirling Historical Society.