Orangetown has a laudable history of supporting the abolitionist cause. White families in Palisades, Sparkill, Nyack and elsewhere tolerated or actively supported local free black communities, and Harriet Tubman, the Hesdra family and the Underground Railroad are well known.

What is less well known is Orangetown’s role in slavery leading up to the New York State Constitutional Convention in 1827 proclaiming emancipation for African Americans residing in the state.

Slavery was introduced to the New World in 1626 by the Dutch West India Company to provide essential manual labor for clearing land and building infrastructure. In the Hudson Valley, the division of land into huge patroon estates discouraged free immigration, relying on forced labor in a system of legal, moral and economic legitimization of human bondage.

The historian Kevin Phillips writes about New York in 1790: “Districts where at least one fifth of families owned slaves [ran] along the Hudson River like a sleeve—a baggy Dutch sleeve with its biggest concentrations in Albany, Hudson Valley towns like Kingston, Saugerties, and Poughkeepsie, and especially Manhattan and its neighboring counties. In farm-rich Kings, Queens, and Richmond, 39.5% of white households owned slaves…In the fattest Dutch farming sections of Kings County (Brooklyn)…, the towns of Flatbush and New Utrecht, two out of every three families owned slaves.”

Dutch slaveholders were also clustered in Bergen County and Orangetown. Because it threatened their way of life, they worked to block emancipation. At the 1799 New York State Legislature deliberations on emancipation, Dutch slaveholders “raved and swore by dunder and blixen that we were robbing them of their property,” according to one legislator.

However, the Gradual Emancipation Act of 1799 passed in New York State. Children born to enslaved parents after July 4, 1799 were legally free but had to serve in their masters’ households until age 25 for females and 28 for males.

When the Emancipation Act of 1804 passed in New Jersey, Dutch farmers lobbied for its repeal. When they failed, they circumvented the law by reneging on contracts, restricting the means by which freed blacks could earn a living or own property, and continuing their enslavement through indentured servitude. Dutch political clout was responsible for New York and New Jersey becoming the last states in the north to transition from slavery to emancipation.

The Dutch ideal of “benevolent paternalism” remained influential as late as the 1980s when white historians were still describing slavery on Dutch farms as “comparatively mild bondage.” African slaves were integral to their masters’ family life, although they could not form their own family units or communities. They spoke the Dutch language, celebrated Dutch holidays and worshiped in the Dutch Reformed Church where they were allowed to congregate in the gallery.

Orangetown, because of its access to markets in New York City, was the wealthiest town in Rockland, thus better able to afford slaves than the “frontier” communities further north and west. Of the fifteen wealthiest Orangetown families, fourteen owned slaves.

After emancipation, most freed slaves remained in their masters’ households as indentured servants. Disenfranchisement was enforced by the white community’s control of land and jobs, pushing free blacks to the margins of society. Many left Rockland for New York City.

There is scant documentation of Orangetown’s enslaved population who are typically referred to in surviving legal documents and inventories of livestock by a slave name such as “Cuff.” They were chattel. But because of the Nicholas Gesner diaries, we can glimpse the relations between one master and his slave.

Nicholas Gesner, personally opposed to slavery, bought a slave named Jack from his father, John Gesner, in order to set him free after seven or eight years, but shortly after, Jack was approached by Jacob Concklin, Gesner’s brother-in-law, with a better offer: a plot of land and his freedom after seven years if he’d agree to change masters. Gesner initially refused to sell but later relented. When the seven years were up, Jack asked Concklin for his freedom, but Concklin denied it for another seven years after which he consented to free Jack in exchange for $100. Peter Willsey put up the money, which Jack paid back by chopping wood. Once free, he purchased the first parcel of land in what would become Skunk Hollow. He was given his surname Earnest because of his determination to be a free landowner. By 1820, according to the census, there were still 124 slaves in Rockland County, and by 1830, three years after emancipation, there were none.

The decline of slavery in Orangetown coincided with the decline of Dutch culture and the rise of abolitionist forces. The rural Dutch farmer resistant to change was captured by Washington Irving in 1819 in the character Rip Van Winkle who slept while the world passed him by.