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This history of Dead Neck Island itself is integral to the history of the watershed we protect, as well as nearby Grand Island in Oyster Harbors. Throughout history, the two have been linked together with Dead Neck being an integral part of Oyster Harbors.

In 1658, Oyster Island (the first name for Oyster Harbors), along with Dead Neck, was reserved for the Indians that inhabited the area. Oyster Island was purchased from the Indians in 1737 for 517 English pounds by the Lovell family as a result of a lawsuit that put the Natives heavily in debt. It was then uninhabited for nearly two centuries being used only as salt works and pasture land. At that point in time, Dead Neck Island as we know it today did not exist. It was not an island then but a peninsula or “neck” of land that ran all the way from Dowse’s Beach to the end of Dead Neck with Sampson’s Island being a separate island altogether.

The first people who realized the potential for Oyster Island were Richard and Helen Winfield of Mount Vernon, New York. Over the course of forty years beginning in the late 1800’s until 1921, the Winfield’s acquired title to Oyster Island, now known as Grand Island, 54 acres of Little Island and 77 acres of Dead Neck Island. By 1925, the Winfield’s owned almost all of the property on all the islands except for a few lots that they had sold to eight families. It was then that they all realized that the island needed to be made more accessible, so they received permission from the Town of Barnstable to build a bridge from the mainland to Little Island in 1891. They also built a causeway over the marsh between Little and Grand Islands and constructed the first road on Grand Island. At the same time, Osterville residents were eager to open a channel for boats to travel from West Bay into Nantucket Sound.