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Native Americans

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.

The Hardenburgh Patent and Early Settlement

Bob Hubbell in Calico Indian dress

Bob Hubbell in Calico Indian dress

At about this time, wealthy British interests were busy carving up the region via the 1,500,000-acre Hardenburgh Great Patent of 1708, the largest one ever granted by the British crown. It was named for Johannes Hardenburgh, one of eight patentees who formed a cartel of entrepreneurs and gentry linked by family, religious affiliation, and business relations eager to profit from the development of unsettled lands in the British colony of New York.

The Hardenburgh Patent went unsurveyed and unsettled for nearly 40 years, although shares in it were traded regularly, including to Robert R. Livingston, who made a gift of 5,000 acres in the New Kingston valley to 100 people who had lost their houses when Kingston was burned during the Revolution.

Patentees advertised for people to lease lots within their tracts and so, landless, they came — Revolutionary War veterans, Dutch emigrants from the Hudson Valley, Irish and Scottish immigrants — to carve hardscrabble farms out of forested lands in the Catskills. But opportunity became oppression when lessees, who paid annual rents of livestock, crops and cash but could not outright purchase their farms, realized that privileged distant landlords were profiting from their labors.

The Anti-Rent War of the 1840s involved many Middletown farmers who banded together in “calico Indian” disguises to thwart farm evictions, harass sheriff’s deputies and protest the feudal system. The conflict came to a head with the shooting death in 1845 of Undersheriff Osman Steele in Andes. The lease-hold system of the great land patents was soon abolished legislatively.

Among the settlers to have signed leases were four Dutch families who came to the valley of the East Branch from Ulster County in 1763. Five more families joined them during the next eight years; all are believed to have maintained friendly relations with the Indians until the time of the Revolution, when the Europeans went back to Ulster County for the duration of the conflict. By the time the settlers returned to Middletown, the Indians had been driven westward.

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