Long before Middletown was Middletown, this area was occupied seasonally by Lenni Lenape (Delaware) Indians. The Lenni Lenape were named by the English the “Delaware” Indians as they lived on the shores of Delaware Bay and the river that emptied into it. They were an Algonquian speaking tribe (as opposed to Iroquoian), and their territory ran from the headwaters of the Delaware and Susquehanna Rivers south to the Potomac. The Oneidas and Tuscaroras occupied lands to the north and west; the Mohicans, Esopus and Wappingers to the south and east.
The Munsee band was among two subtribes of the Lenni Lenape and it is this group that is believed to have occupied a site along the East Branch of the Delaware River between Arkville and Margaretville. Sometime after 1715, historians believe they conveyed the territory to the newly arrived Tuscaroras.