Early in the seventeenth century, the beautiful Island known as Manhansack-aha-quash-awamock (“an island sheltered by islands”) was the peaceful home of the Manhanset tribe of Indians. Their Sachem, Pogatticut, was the Grand Sachem of most of the tribes on Long Island.
The first white man to visit the Island, James Farrett, came here in 1638 as an agent for Sir William Alexander, Earl of Stirling, who had received enormous grants of land in America from King James I of England. Farrett chose Shelter Island and Robbins Island as his 1,000 acre reward for his services to the Earl. He negotiated with the Indians for possession of the islands. Shelter Island then became known as “Mr. Farrett’s Island.”
1641: Farrett sold his islands to Stephen Goodyear of New Haven and for the next ten years Shelter Island was known as “Mr. Goodyear’s Island.”
1651: Goodyear sold the Island to four merchants active in the Barbados sugar trade: Thomas Middleton, Thomas Rouse, Constant Sylvester and Nathaniel Sylvester. When these gentlemen visited the Island, Nathaniel Sylvester decided to make his home on the Island and selected the site for his house, which is thought to be a short distance from the current location of the present Sylvester Manor House.
1652: Nathaniel Sylvester and his partners signed an agreement on how they would do business. Shelter Island and Robbins Island were organized to be the supply plantation for their sugar plantations in Barbados.
1656-1661: Quakers were persecuted in New England and many found refuge with the Sylvesters on Shelter Island.
1673: Nathaniel Sylvester became the sole proprietor of Shelter Island after his partners passed away. 1680: Nathaniel Sylvester passed away and bequeathed Shelter Island to his five sons in equal parts.
1695: Giles Sylvester was the eldest son of Nathaniel Sylvester. He came to own four-fifths of the Island after three of his brothers passed away. Giles sold one-quarter of the Island to William Nicoll. The Nicolls became a prominent Island family.
1700:Nathaniel Sylvester II sold 1,000 acres of land in the center of the Island to George Havens. The Havens family became another prominent family on the Island.
1730: The first Town Meeting was held on April 7. There were twenty men living on the Island (six of whom were named Havens).
1743: The first church was built on Shelter Island, on the location of the present-day Presbyterian Church.
1791: First known date for established Shelter Island School.1846: Jonathan Preston began the first scheduled ferry service between Dering Harbor on Shelter Island and Greenport on the north fork of Long Island.