Long Island's maritime Underground Railroad: A voyage to freedom for the enslaved in the 1800s

On a chilly night in 1838, James Lindsay Smith’s escape from slavery found him sleeping on cotton bales aboard a steamboat cruising on Long Island Sound.

Even so, Smith, then on the cusp of freedom, felt “depressed in spirits and cast down” amid a liberation pursuit that started with him fleeing bondage in Virginia.

“The climate had changed much since I left home, I was out of money and among strangers; my heart sank within me, for I was faint and hungry, and had no means to pay for my supper,” Smith said in his narrative.

Smith’s escape is one of many in which Black people used the region’s waterways to escape the shackles of slavery through what came to be known as the Underground Railroad, a network of people who helped spirit enslaved people to freedom through secret routes beginning in the 1800s.

The National Park Service has expanded its definition to include "the efforts of enslaved African Americans to gain their freedom by escaping bondage."

As the nation's 250th anniversary approaches, along with next year's 200th anniversary of slavery being abolished in New York, emerging scholarship points to an expanded time frame for the Underground Railroad and the use of maritime routes as a common form of escape among freedom seekers. That could include self-emancipation by boat and other means, such as when enslaved people led a mutiny aboard La Amistad, which ran aground off Long Island.

Voyages to freedom

“Almost nobody escaped very long distances by land. Most people who escaped long distances did so by water, and almost everyone who escaped from the coastal far South did it on a ship or a boat,” said Timothy Walker, a history professor at the University of Massachusetts Dartmouth who edited “Sailing to Freedom: Maritime Dimensions of the Underground Railroad.”

On land, travel was often slower, in part because people had to walk and find places to shelter, all the while being tracked by slave catchers. But over water, freedom seekers could travel vast distances on boats carrying cotton and other goods up the Atlantic coast, or on other vessels.

Ships had many hiding places that could stow away enslaved people, and sometimes Black people could pass themselves off as free seamen.

On Long Island, some historians say escape across the Sound was likely because enslaved people often lived in coastal communities and were familiar with the waters. They could be helped along by some of the area’s residents opposed to slavery, and Black seamen, who could bring back news from distant lands.

 Jonathan Olly, a former curator for the Long Island Museum and current director of museum collections at the New Hampshire Historical Societ y, said a person living in a coastal community on Long Island at the time would very likely have had maritime experience.

“So that expertise can give you an advantage, because that could allow you maybe a little bit of personal freedom in what you're being forced to do, or it could be the key to your freedom,” he said.

In 1799, New York passed a gradual end to slavery, but many remained enslaved until 1827, historians say. After that, slavery existed in the state in other ways, including on ships that carried enslaved people and in the recapture of fugitive slaves.

For instance, the wealthy sometimes financed voyages to obtain slaves, historians say. There were also bounty hunters who sought to kidnap free people of African descent and sell them back into slavery.

Northeast networks

Other northern states, such as Massachusetts and Connecticut, and areas like New Bedford, Massachusetts, had a climate considered safer because of anti-slavery sentiments held by the significant Quaker population active in the whaling business in the region, Walker said.

Despite the dangers in New York City, abolitionists like David Ruggles, the Quakers opposed to slavery, and others helped fugitive slaves on their journey to freedom.

Ruggles was “the leader of a network with connections to antislavery activists in Baltimore, Philadelphia, New England, and upstate New York,” according to Eric Foner’s “Gateway to Freedom: The Hidden History of the Underground Railroad.”

“He regularly scoured the wharfs, on the lookout for fugitive slaves,” the book notes.

At some point, Smith found Ruggles after he and two other enslaved people fled Virginia by canoe and sailboat.

Hindered by a childhood leg injury, his fellow travelers temporarily left him behind on land to avoid capture. Together again, they took a boat to Philadelphia before the other two decided to work aboard a vessel headed to Europe.

Smith went alone to New York, receiving two letters from Ruggles and help in getting to Connecticut and Massachusetts. Once there, Smith found freedom.

A shoemaker, Smith started a business and preached. He eventually married Emeline Minerva Platt. Two of his three daughters became teachers, and his son followed his father into the shoe business.

Ads for runaway slaves

On Long Island, the record of escapes is often told through the narratives of formerly enslaved people and newspaper advertisements seeking to bring them back. Some of them are laid out in the book “Long Road to Freedom: Surviving Slavery on Long Island.”

One 1792 newspaper notice in The Connecticut Journal of New Haven sought a man named Bud, who was described as being stocky but not too tall. The notice states that the same night Bud is believed to have left, a boat disappeared from Huntington Harbor.

“The same night a small boat was taken from Huntington harbour, in which it is supposed Bud went off, and that some of his colour accompanied him. The boat has two masts, with sprit sails, for the securing of which a generous reward will be given," the advertisement read.

In another notice from The Royal Gazette of New York, a Long Island slave owner sought a reward for Ben, who had “a scar under one of his eyes from a burn,” walked with a limp and had a yellow complexion.

The advertisement used a phrase that was repeated in other notices: “All Masters of Vessels and others, are desired not to harbor or conceal said slave, as they will answer it at their peril.”

Walker said traveling across the Sound was difficult, depending on the type of vessel used. The area closer to New York City has harsh currents, and traveling from the East End to Connecticut could be a long distance.

Walker noted that one of the easiest ways to get from New York to Boston in the 1820s and decades later was via the Fall River Line, a company that owned steamships that traveled across the Sound.

“A lot of enslaved people used that to get from New York, where they were not very safe, to Boston, where they were relatively, significantly safer,” he said.

Return to bondage

Although many escaped, some enslaved people were caught and returned to their masters.

In 1845, the Savannah Georgian reported that an enslaved man called James was caught on a British vessel lying near Long Island, according to “Sailing to Freedom: Maritime Dimensions of the Underground Railroad.”

Another attempted escape comes from a man named Venture Smith, who recorded what a Library of Congress article called the earliest slave narrative in the United States, describing his birth in West Africa around 1729 and his eventual life on Long Island.

On Fishers Island, Smith and several others attempted an escape, grabbing clothes and food, before taking their enslaver’s boat and fleeing, according to the narrative.

“When we had gathered all our own clothes and some more, we took them all about midnight, and went to the water side,” he said.

But after several setbacks, Smith returned to his enslaver.

Smith, whose birth name was Broteer Furro, was later sold to three Connecticut enslavers but eventually paid his way out of bondage at the age of 36 after making a deal with another slaveholder, according to the Long Island Museum.

Smith later returned to Long Island to help pay for the freedom of his wife, Meg, and his three children, as well as three Black men, according to the museum and his narrative.

Reflecting on his life, Smith said: “But amidst all my griefs and pains, I have many consolations; Meg, the wife of my youth, whom I married for love, and bought with my money, is still alive. My freedom is a privilege which nothing else can equal.”

Untold stories of fleeing slavery

Even with these glimpses into days gone by, far more is to be known, understood and recognized, historians say. Some stories might never have a written account, as many people who fled slavery settled into quiet lives and didn’t discuss their experiences.

Moreover, many who may have helped harbor an enslaved person did not keep notes about abolition activities that could cost them their lives. And with that, any written proof might have drifted away.

Yet some believe the echoes of those clandestine travels are reverberating today in other ways.

In Sag Harbor stands the St. David AME (African Methodist Episcopal) Zion Church. Started by whalers in the 1800s, the church is within close reach of Sag Harbor Bay.

Inside, there are crawl spaces and trapdoors that might be used to hide freedom seekers. And in the steeple, a bell hangs. Maritime experts have said its ringing was a call for help, according to Georgette Grier-Key, executive director of the Eastville Community Historical Society.

“We infer that when that bell rang, you know, the whalers knew that there was some precious cargo that had to be taken up North,” Grier-Key said.

The Rev. P. Thompson, the church’s inaugural leader, was a friend of reformer and abolitionist Frederick Douglass. Nearby, several homes on Liberty Street may have been part of the Underground Railroad.

Yet, none of those places are noted on the National Park Service’s Underground Railroad listings, in large part because there are limited written records, she said.

Still, Grier-Key believes it is very possible that the Black people who worked on and knew the area’s waters intimately would go there to begin their voyage toward freedom.

“There’s a direct path from the church to Liberty Street to the water,” she said.