sailing aboard the 1906 tall ship Mary E out of Greenport Harbor is to relive the village’s maritime heritage. As the crew hoists the sails, the Mary E glides eastward into Gardiner’s Bay, following ship routes established long ago.

Centuries ago tall ships plied these same waters, allowing many employment opportunities for carrying cargo to the early settlers. Greenport’s deep water harbor invited seafaring commerce of all kinds: rum and molasses from the Caribbean, building materials and essential goods from New England. Greenport’s maritime reputation thrived in the 1790s when it became a major whaling port. More than a hundred whaling ships departed from Main Street Wharf.

Local maritime industries prospered to meet the needs of the whalers – ship building and repair, ships chandlers, barrels filled with provisions. In spite of the decline of the whaling industry in the mid-1850s, Greenport’s status as a vital marine hub continued. Baymen sought scallops, clams, Menhaden, oysters – growing industries that provided jobs and income for the community.

Local sailors earned a somewhat more illicit income from “rum running” during Prohibition. Their small, speedy boats delivered the contraband liquor off-loaded from large liquor-carrying yachts drifting in the Atlantic just beyond the jurisdiction of the US Coast Guard. Some of these same seamen redeemed themselves during World War II by donating their boats to the Coast Guard’s Picket Patrol that guarded the coast against incursions by German U-boats.

Today, Greenport’s scenic harbor draws boaters and visitors from all over the world. The harbor abounds in tall ships, commercial fishing boats and charters, daily cruise and pleasure boats, maritime festivals and nautical crafts, all of these keeping Greenport’s rich Maritime History alive.