Warranawonkong chiefs transferred to Governor Stuyvesant the Groot Plat or Great Plot, as it was called, in which Kingston is now situated. These lands are said to be the first for which Europeans received a title from the Indians, and are somewhat indefinitely described in the treaty with them of 1665 to which reference has been made. They were conquered by Captain Kreiger in 1663, and embraced three townships in southwestern Ulster. Chronology next takes us to the extreme south of Orange County. Here Balthazar De Hart and his brother Jacob, purchased of the Indians "the Christian patent lands of Haverstraw." They were on the south side of the Highlands and extended from the Hudson westward to the mountains. On the presumption that they were included in the boundaries of New Jersey, the Harts soon transferred them to Nicholas Depues and Peter Jacobs Marius, and purchased another tract north of them in 1671, which was bounded by the Hudson River on the east and the mountains on the south. This became the property of Jacobs. They also purchased a tract north of the previous purchase, and including a part of it, which was called Abequerenoy, and passed from them to Hendrick Ryker.

On the north a Huguenot, Louis Du Bois, with some friends who had been driven from France by religious persecution, located first at Esopus in 1660; and in September, 1667, after purchase from the Indians, twelve of them became patentees of a tract of 36,000 acres lying north of the Redonte Creek, as the Warranawonkong was then called. The patent was obtained from Governor Andros in the names of Louis Du Bois, Christian Doyan, Abraham Hasbroucq, Andre Le Febvre, Jean Hasbroucq, Pierre Doyan, Louis Beviere, Anthony Crespel, Abraham Du Bois, Hayne Frere, Isaac Du Bois and Simon Le Febvre, "their heirs and others." Nine families immediately settled on the land and founded New Paltz.

Between Haverstraw and New Paltz Patrick Mac Gregorie, David Fosbruck, his brother-in-law, and twenty-five others, who were mostly Scotch Presbyterians, occupied lands at the mouth of the Waoraneck, and Mac Gregorie purchased for them 4,000 acres on both sides of Murderer's Creek, on which they settled. Mac Gregorie built his cabin on Plum Point, then called Conwanham's Hill, and the cabins of his associates were in the vicinity, and on the south side of the creek David Toshuck, the brother-in-law, who subscribed himself "Laird of Minivard," established a trading post. "Within the bounds of the present county of Orange this was the first European settlement," says the historian, but the precise date is not given. Stickney thinks the year was 1684, but it was probably a little earlier, as about that time Mac Gregorie entered into the military service of the State without perfecting his patent, mistakenly trusting Governor Dongan to protect his interests, who, in 1684, obtained from three Indian owners their title to a tract extending from New Paltz along the Hudson to Murderer's Kill, thence westward to the foot of the high hills, and thence southwesterly along the hills and the river Peakadasank to a pond; and the same year added by deed from several Indians another large tract of the land called Haverstraw. These lands included a part of those which the Indians had previously sold to Mac Gregorie, and others which they had sold to Stephanus Van Cortlandt. The latter had preserved his deed, and succeeded in obtaining a patent attaching them to his manor across the river. Mac Gregorie was killed in the Leslie revolution of 1691. Governor Dongan sold his two purchases to John Evans in 1694, and the latter then proceeded to dispossess Mac Gregorie's widow and her family of their home, when he granted only leases to them and the other Scotch settlers. After some years, however, the Mac Gregorie heirs, in consideration of their original claim, obtained a patent of the Plum Point farm and a mountain tract.

The fourth and largest settlement was made adjoining "the Christian patented lands of Haverstraw" by emigrants from Holland, mostly of the Reformed Dutch Church. They were granted a township patent in March, 1686, under the name of the town of Orange. There were sixteen trustees of this grant, which began at the mouth of the Tappan Creek, extended north to Greenbush, and thence easterly and southerly back to Tappan Creek. The center of the township was Tappan, where a church was organized. The trustees of the grant were Claessen Cuyper, Daniel De Clercke, Peter Harnich, Gerritt Stenmetts, John De Kries, Sr., John De Kries, Jr., Claes Maunde, John Stratemaker, Staaes De Groot, Aream Lammatees, Lamont Ariannius, Huybert Gerryts, Johannes Gerryts, Ede Van Vorst, Cornelius Lammerts.

A vast tract of land immediately west of Haverstraw was conveyed to Daniel Honan and Michael Hawdon, January 25, 1696. Adjoining this on the south were certain tracts containing 2,000 acres which were granted to Samuel Bayard. The Indian deed for this and other purchases was covered by Lucas Tenhoven and embraced 100,000 acres, for which no patent was issued.

Between the Haverstraw lands and the township of Orange was the rocky bluff known as Verdrietig Hook, including Rockland Lake, which became the subject of controversy between the John Hutchins Company and Jarvis Marshal & Company, both parties having obtained deeds, but that of the latter proved to be of prior date (Sept. 27, 1694). A few years later, in 1708, a patent was issued to Lancaster Syrus, Robert Walters and Hendrick Ten Eyck, covering the vacant river point described as beginning at the south bounds of Haverstraw, extending west to Welch's island, thence southerly to the lower end of the island, thence east to the creek running from the pond of Verdrietig Hook, and thence north to the place of beginning, "except the grant of Honan & Hawdon."

Ruttenber and Clark's history states that the indicated foregoing patents covered the entire district from the New Jersey line to New Paltz and west to the line of the Shawangunk Mountains.

Here is the proper place for some statements made by David Barclay in his paper on Balmville read before the Newburgh Historical Society in 1899. He said that Captain John Evans in 1694 obtained from Colonel Fletcher, then Governor of New York, a patent for a tract of land on the west shore of the Hudson, extending from Stony Point to the south line of New Paltz, and westward to the Shawangunk Mountains, including two-thirds of Orange County and parts of Ulster and Rockland Counties, and estimated to contain 650,000 acres. The only settlement thereon at that time was that of Major Gregorie's heirs and followers at Murderer's Creek in the present towns of Cornwall and New Windsor. The patent was afterward annulled by an act of the assembly, which was confirmed, and the title reverted to the crown. Included in these lands must have been those unjustly transferred to Evans in 1694 by Governor Dongan "under the title of the lordship of the manor of Fletcherdom." Ruttenber says that the Evans patents, with others, were for a long time a disturbing element, and were entirely undefined except in general terms.

Near the close of the 17th century there was active competition in the extinguishment {sic} of the Indian titles and obtaining patents, and several patents were granted. Three of them, to associations, were issued at the following dates: Chesekook, December 30, 1702; Wawayanda, March 5, 1703; Minisink, August 28, 1704.