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Follow the Drinkin’ Gourd to Freedom

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The Underground Railroad often conjures images of a Gone With the Wind antebellum South, but early New York State — which President Abraham Lincoln never won — was itself no haven for runaway slaves, particularly New York City.

An ever-shifting web of secret routes and friendly abolitionists, the Underground Railroad hummed in the 19th-century Hudson Valley. It laid its own virtual tracks across the county at the same time the steam railroads made their mark, in fact adopting the same slang (“stockholders” funded “stations” run by “conductors” who were predominantly black and helped travelers from one stop to the next). 

Colonial New York was a full-fledged slave state. Before independence, the Hudson Valley’s big manors exploited the labor to run their farms and businesses. Westchester’s Quakers, whose creed required that “friends disown slaves or face excommunication,” were one of the only groups to decry owning another human being.

The nation’s first chief justice of the Supreme Court, Katonah resident John Jay, helped lay abolition’s legal groundwork in forming the New York Manumission Society with, among others, Alexander Hamilton and (in a true case of politics making strange bedfellows) Aaron Burr. New York slave owners had helped kill a state bill (that Burr supposedly initiated) banning slavery outright, leaving the two Founding Fathers to argue for a incremental push toward abolition.

The South’s slave-driven sugar and cotton exporters were propelling many of New York City’s booming markets. Industries from banking and shipbuilding to insurance and tourism stood to lose if abolition succeeded, although most cities were familiar with slaves traveling from one owner to the next.  

Decades of fierce activism, however, turned the tide, and in 1827, a new bill outlawed servitude in New York State. The number of slaves in the state dwindled to 55 by 1830. A debate still raged over abetting fugitive slaves from other states. But by the mid-19th century, New York had become free country and a key thoroughfare between the Upper South and New England for those seeking freedom from servitude.  Westchester’s access to several key waterways and trade routes both north and west made it a well-tracked byway. The escape route for many fugitive slaves included traveling by boat up the Hudson River to Peekskill.

The first stop in the county was Quaker William Sands’ Peekskill “Safe House.” A secret stairway led to a concealed room that sheltered runaway slaves until they could make their way farther up the Hudson. Friendly sailors hid escapees on their boats across the Long Island Sound, avoiding bustling Manhattan for quieter suburban farms. The Mott brothers, part of the Quaker community in Larchmont, often took in the runaways as they traversed to Northern Westchester.

 From there, Tarrytown’s Foster Memorial AME Zion Church used a false wall near the pulpit for a room where slaves could find home-cooked meals and lodging. Boats took fugitives destined for Canada, while other now-free blacks looked to settle in Westchester. Over the years, parishioners at Foster Memorial included Frederick Douglass, Harriet Tubman, Henry Ward Beecher, and Sojourner Truth.

A rumored hidden tunnel off Boston Post Road in Larchmont was said to have run toward the Barker-Quaker Cemetery, mainly to confuse slave owners’ scent-tracking hounds. In Brooklyn, the Plymouth Church of the Pilgrims built unseen tunnels to transport slaves toward Putnam and Dutchess Counties.

Groups across the county, often led by newly freed black communities, raised money to donate clothes that would help fugitives fit in as they traveled. Quaker communities from Chappaqua to Scarsdale worked to resettle and enfranchise former slaves. In the public sphere, John Jay II became New York’s leading pro bono attorney for slaves, a job that, as one journalist noted, came “at great risk to his [Jay’s] social and professional standing.”

By some estimates, more than 100,000 made their way on the Underground Railroad between 1810 and 1850. For many “following the drinkin’ gourd” (in the words of the 1928 folk song that referenced runaway slaves guided north by the Big Dipper), Westchester was a stop on the way to a new life.  


Dan Robbins majored in history and American studies at Cornell University and remains an unabashed history buff, particularly when it comes to his own backyard.