Long before European settlement, Native Americans inhabited the South Oyster Bay area for millennia. As the Dutch expanded their New Netherland colony in the 1600s, land treaties became necessary. In 1639, Mechowodt, Sachem of the Massapequa (then Marossepinck), signed an "Indian Deed" at Fort Amsterdam, ceding a large tract of western Nassau County, including part of Massapequa, to the Dutch West India Company. This area around Oyster Bay was noted as "Fort Neck" by Europeans due to the presence of two Indigenous forts.
The Mechowodt Agreement aimed for peaceful coexistence, allowing his people to remain on their lands with continued access to their traditional livelihoods, while the Dutch pledged protection. However, land sales continued. In 1658, Mechowodt's son, Sachem Tackapausha, sold more of south Massapequa to English settlers from Oyster Bay, though Native Americans retained some land use rights. Tackapausha became a significant leader on Long Island. He reaffirmed the 1658 sale in 1660 and received payment. A promised 1656 treaty with the Dutch, signed by Governor Stuyvesant in 1660, included Dutch protection for the Massapequa and an agreement for mutual consultation on dealings with other Indigenous groups. Stuyvesant also fulfilled his promise to build a fortified trading post at Fort Neck. These early agreements and sales marked a significant shift in land ownership and the relationship between the Dutch/English and the Massapequa people.