The following brief note stems from my review of Robert Bolton, Jr.’s  History of the County of Westchester from its First Settlement to the Present Time.  (New York: Alexander S. Gould, 1848), p. 337.

The interesting parts of the story of Westchester have much to do with Catherine Filipse (nee van Cortlandt).  Her habit of riding through the woodlands roads atop a horse rather frequently is what led to the infamous Headless Horseman story.  In this tale related to the history of Westchester county, she is said to be riding her horse often to check on the status of the new church being built. 

For those of you local history experts who know where I am going with this– yes, this was the famous church of Sleepy Hollow.

Following Catherine’s death, it is said that the mist seen to rise above swampy woodland floors would turn into Catherine, who would once again ride her horse across her lands in order to ensure its security.  The author of the Headless Horseman tale, Washington Irving, simply changed this local legend a bit and made it a story about a Prussian soldier who was beheaded, keeping the local story of Catherine alive, redefining it along the way like many writers do.

This particular tale I focused on due to the insight it provided me regarding the behaviors of the Dutch and Indians during the late 17th century.   This is a unique series of notes that refer to legal manusmission of the “Indian squaws” offered to Catherine by a local businessman.  To the Dutch, business is simply business it appears.


In a book written in Dutch on this region, Het notitie boeck der Christeutycke Kerck op de Manner of Philipsburgh (translated as The Memorandum book of the Christian Church of the Manor of Philipsburgh) a motto was written: “Endraght maakt magt, maar twist verquist,” which translates to “Unity makes right, but discard squanders”.   Travellers who passed through New Netherlands took advantage of the recent land claims and many came to view their purpose to relate to the need to control the savagery which was then taking place amongst natives.  

Following decades of buying, dividing and sub-dividing land deeds purchased from local Natives, the valley in Philipsburgh, West Chester County, was settled by members of the Van Cortlandt family in the late 1600s, including Catherine van Cortlandt who married Frederick Philipse. As the Van Cortlandts began inhabiting sizeable estates, they were able to afford some fairly expensive provisions.  Their religion, borne of trinity faith, is told by their family baptismal and communion “bekers” or vessels:

“..the first richly engraved with floriated tracery, bears the name of Frederych Flypse, and stands about seven inches high.  The second is also richly engraved with antique figures, representing angels, birds, fruits and flowers, beside three ovals containing emblematic figures of Faith, Hope and Charity, near the top is engraved the name of Catherina van Cortlandt, this cup stands nearly six inches and a half high.”

The size and shape of these vessels symbolized this family’s belief in religion and their family’s hierarchy.  The Husband’s Communion vessel was taller than that of his wife, but her vessel bore the symbols of trinity–given as Faith, Hope and Charity–and the four elements represented by the spirits and animals, each symbolic of conception and the means to conceive.  Catherine Philipse became an important benefactor in the building of the new church in nearby Tarrytown.  In the early days of raising that church, she would passed through on horseback to oversee its construction. 

This family’s land in Philipsburgh extended from the “Spyten Devil’s kill, running north along [Hudson] river, until the kill of Kitchawona was reached.”  In The Memorandum book… on this region is given an account of an early reason the Dutch so actively settled here:

“to indicate further in what manner and good affection these first Christian inhabitants have shown in the middle of heathenism, and with and about heathens to live, as true Christians, having first thought good and highly necessary, on the Lord’s day, to gather together and in a place for that purpose fit, to pray together, God the Lord with the whole heart to praise and thank him with psalms and hymns, &c.”

The goals of new settlers thereby became not only to make land claims and learn the uses for the resources.  It was also decided that the indoctrination of religion into the savage culture was of utmost importance.  Often the initial plans were to learn about their Great Spirit and change the Native Americans’ mindset.   What happened instead at times was that local Natives became slaves and  serves these young European communes.  During her dying days on January 7, 1730, Catherine Philipse released “Matty and Sarah, my Indians or muster slaves” through legal manumission.  Such used of Native Americans as early slaves existed in throughout the lower Hudson Valley region as early as 1705, when the legal records record Elizabeth Leggett giving to her daughter two negro children, “born of the body of Hannah, my negro woman,” and “Robin, my Indian Slave.”   Another record of such Native American slavery in this part of the New World is seen in New York city documents, which note Jacob Decay serving as a dealer of “Indian squaws.”