Tracing the Roots of Black History in Pine Plains and Milan

This year, Pine Plains marks a major milestone with the bicentennial of its formation in 1823. But the area’s ties to African American history – commemorated nationwide as part of February’s Black History Month — stretches back even further, with roots in both slave-holding and the abolitionist movement that followed. 

The ownership of African-born slaves for agricultural and domestic labor began in the region as far back as the 17^th century. By 1790, according to the Little Nine Partner’s Historical Society, which records Pine Plains history, New York was the “largest slave-holding state north of the Mason-Dixon line,” with many slaves held in New York City and throughout Dutchess County and the Hudson Valley.  

Locally, slaves were kept by a number of prominent families. Census records show the family of influential land owner and politician Lewis Graham – the builder and original occupant of the Graham-Brush House – owned several slaves. Other slave-holders included Fyler Dibblee, a librarian and town supervisor who together with his father in the early 1800s ran the Ketterer Hotel, at what is now the site of the town park on the southeast corner of Church and Main streets.  

Abolitionist sentiment was beginning to take hold in the United States. Across the Northeast, efforts to eliminate slavery ramped up with the first set of gradual abolition laws beginning in 1799. In 1817, New York passed “An Act Concerning Slaves and Servants,” which provided for the eventual freedom of every child born to a slave after July 4, 1799. Records show that Fyler Dibblee, as a result of the act, documented the birth of a male child from a slave mother in 1818.   

Disputed Burial Grounds 

Much of the region’s Black history is reflected in the remains of segregated cemeteries for people of color. The Turkey Hill lot in the neighboring town of Milan was established as a so-called “colored” lot after the death of Jacob Lyle, a soldier in the Revolutionary War who was buried on the one-acre parcel he had purchased in 1813. (In a well-documented case, Lyle, who is recorded in the federal census as a person of color, spent six years petitioning unsuccessfully for his war veteran’s pension.) After the death of Lyle and his wife, the Turkey Hill property was transferred to a Black neighbor, Nancy Bradford, who was ultimately buried on the plot as well.  

There are several obituaries detailed in local newspapers referencing other African Americans being subsequently buried in the Turkey Hill lot through the start of the 20^th century, including Lemuel Jackson, whose obituary appeared in The Pine Plains Register and Herald in 1927.  

During the 1930s, the lot was erroneously assigned a historical marker as an Indigenous burial ground – a mistake noted by local historian Bill Jeffway, the Executive Director of the Dutchess County Historical Society, and which the town of Milan sought to amend in its own bicentennial commemorations in 2018. Jacob Lyle is now listed on the veteran honor roll at Milan’s town hall.  

Emancipation & Safe Harbor 

In 1827, New York became the first U.S. state to pass full emancipation of enslaved people. As Southern states continued to defend slavery – a divide that culminated with the 1861-65 Civil War — the need mounted for secure locations to help hide fugitive slaves escaping the South for free states in the North.  

Research shows the Mid-Hudson Valley and Northern Dutchess County played a role in the Underground Railroad. The Dutchess County Anti-Slavery Society, whose members included Reverend William N. Sayre of the Pine Plains Union Meeting House and Presbyterian church, held its first annual meeting in 1839 in Pleasant Valley.   

No official documentation exists proving Pine Plains served as a way station along the Underground Railroad. But several residents of Pine Plains and nearby regions lay claim to oral histories about their current-day homes serving as part of the Underground Railroad. Local Keary Hanan, whose home on Hammertown Road includes a hidden ladder and crawl space disguised behind a bookcase, says the previous owners of the house claimed the structure was a safe stopping point for escaped slaves moving north.  

By the 1930s, the African American population of the area had shrunk substantially. But for Pine Plains and surrounding areas, the region’s ties to Black history continue to hold special significance.