History — From the December 2014 issue

Gateway to Freedom

The origins of the Underground Railroad

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On September 4, 1838, a twenty-year-old fugitive slave named Frederick Bailey arrived in New York City. He had long hoped to escape from bondage, gazing out at the ships on Maryland’s Chesapeake Bay as a child and seeing them as “freedom’s swift-winged angels.” He secretly taught himself to read and write, understanding, he later wrote, that knowledge was “the pathway from slavery to freedom.”

Bailey’s first attempt at flight came in 1836, when he and four friends devised a plan to abscond by canoe onto the bay and make their way north. But the plan was discovered, and the five were arrested, jailed, and returned to their owners. Two years later, while working as a caulker in a Baltimore shipyard, Bailey again plotted his escape, this time with the assistance of Anna Murray, a free black woman he planned to marry. Murray provided the money for a rail ticket, and Bailey borrowed papers from a retired black sailor that identified him as a free man. Dressed in nautical attire, he boarded a train, hoping to reach New York City.

“Plymouth Church,” by Amani Willett, from a series depicting significant locations in the history of the Underground Railroad. His work will be on view in January at the Ruth S. Harley University Center Art Gallery, Adelphi University, in Garden City, New York. Courtesy the artist

“Plymouth Church,” by Amani Willett, from a series depicting significant locations in the history of the Underground Railroad. His work will be on view in January at the Ruth S. Harley University Center Art Gallery, Adelphi University, in Garden City, New York. Courtesy the artist

Despite the short distance — less than two hundred miles — the trip proved arduous and complicated. Thirty-five miles north of Baltimore the passengers had to disembark and cross the Susquehanna River by ferry. At Wilmington, they boarded a steamboat bound for Philadelphia. There, Bailey later recalled, “I inquired of a colored man how I could get on to New York.” The man directed him to a depot, from which Bailey took a ferry to Camden, New Jersey, then the Camden and Amboy Railroad to South Amboy, then another ferry across the Hudson River to a dock at the foot of Chambers Street. Less than twenty-four hours after leaving Baltimore, he landed on the free soil of New York City.

In spite of his exhilaration, Bailey was frightened, alone, and had no idea what to do next. He wandered around and eventually encountered a fugitive slave he had known in Maryland who warned him that although New York was a free state, slave catchers roamed the city’s streets. Shortly thereafter, Bailey had a stroke of luck: a “warm-hearted and generous” black sailor directed Bailey to the home of David Ruggles, at 36 Lispenard Street, not far from the docks. Ruggles was the secretary and prime mover of the New York Committee of Vigilance, which had been founded three years earlier to combat an epidemic of kidnapping. Many years before Solomon Northup drew attention to this problem in his widely read memoir, Twelve Years a Slave, free blacks, frequently young children, were abducted from New York’s streets for sale into Southern slavery. In addition to providing fugitives from the South with shelter and transportation, the Vigilance Committee provided legal representation if they were apprehended.

Ruggles took Bailey into his home and advised him to change his name to help avoid recapture: Frederick Bailey now became Frederick Johnson. The fugitive summoned Anna Murray to New York at once, and a few days later the couple married in Ruggles’s parlor. But Frederick Bailey did not remain in New York. Ruggles, who knew that the situation of fugitives in the city was precarious, encouraged him to leave. He gave Frederick a five-dollar bill (more than a week’s wages for a manual laborer at the time) and a letter of introduction, and told the couple to head to New Bedford, Massachusetts, where another black abolitionist would help them. In the fall of 1838, having discovered that in New Bedford families with the surname Johnson were “so numerous as to cause some confusion in distinguishing them,” Frederick changed his name one more time. Henceforth he would be known as Frederick Douglass.

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is the DeWitt Clinton Professor of History at Columbia University and the author of numerous works on American history. This essay is excerpted from Gateway to Freedom: The Hidden History of the Underground Railroad, out in January 2015 from W. W. Norton.

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