PIONEERS - NY TO CANADA
Jacobus Vandewater and Rachel Van Kleek are most likely the pioneer settler family that moved from Poughkeepsie to Hay Bay around 1795 as referred to in the Pioneer Life on the Bay of Quinte.
VANDEWATER FAMILY: (as in the PLBQ)
"The many descendants of the Vandewater family to be found in Prince Edward County, Hastings and Lennox counties are of Dutch descent. The family came from Holland and settled in New York when that place first became a British possession. They removed to Boston, where they carried on a large printing business, some of the members being known as the "King's Printers." They must have been persons of considerable standing, for Vandewater street in New York City was named after the family; and for services rendered to the British Government, James Vandewater, who was afterwards the Canadian pioneer, received a grant of land on Chesepeake Bay, in the State of Maryland, to which State he removed prior to the War of Independence. When the colonies pronounced their allegiance to the crown, James threw in his lot with the revolutionists and served under George Washington. He sent his family to Poughkeepsie as he found his home unsafe for them owing to the proximity of the coast and of the indians, who were in sympathy with the British. As he did not return to Maryland until peace was declared, it is to be assumed that he remained with the army till the conclusion of war. But on his return home he found his land taken up by squatters, whom he was unable to dispossess owing to the unsettled state of the country and the law. It is narrated how that, in a fit of anger at finding his property in such a plight, he burned his deeds to the land and left the country, because he thought there was no justice to be obtained in it.
James Vandewater made his way from Poughkeepsie to Oswego, thence to Hay Bay, where he settled about 1795. He died in 1833 (sic - probably 1823); the homestead at this place being still in the possession of one of his descendants. His sons, John and Peter, made their way up the Bay as far as Sidney, where John bought lot 30, 2nd concession, and Peter, lots 29 and 30 in the 6th concession of Sidney."
Source: Pioneer Life on the Bay of Quinte (PLBQ), 1904, pp. 841/2.