Seeking Escape from Enslavement, Many Found Freedom at Sea

By Skip Finley

“I crossed the waters to come here and I am willing to cross them to return.”

Venture Smith (c. 1729 – 1805), born Broteer Furro in West Africa around 1729, was kidnapped at age six and sold into slavery in Rhode Island. Smith did not, to our knowledge, travel to Martha’s Vineyard. But his story is a useful reminder as we celebrate Juneteenth on the Island that although New England abolished slavery earlier than the rest of the country and contributed some 30,000 Union lives in the Civil War that ended it, the legacy of slavery is not just a part of our national DNA, but very much a part of our local history. The first Vineyarder to die in the American Revolution, it is worth remembering, was Sharper Michael, born a slave in the home of Zacheus Mayhew of Chilmark.

Smith’s statement “I crossed the waters to come here and I am willing to cross them to return,” appears in A Narrative of the Life and Adventures of Venture, a Native of Africa. It is especially relevant as we celebrate Juneteenth this year by welcoming the iconic schooner Amistad to Martha’s Vineyard.

The role of ships and the sea in the origins of African slavery in the Americas is obvious, as new captives had to be transported across the Atlantic. Recently, historians have been looking more closely at the role of the sea in the resistance to slavery. In Sailing to Freedom –Maritime Dimensions of the Underground Railroad, edited by Dr. Timothy Walker and published in 2022, we learn that in a sample of more than 100 slave narratives written between the founding of our country and the end of the Civil War in 1865, more than 70 percent discuss the use of waterways and vessels as means of escape.

The putative “owners” of escaped slaves knew this as well as anyone. In the book Escaping Bondage: A Documentary History of Runaway Slaves in Eighteenth-Century New England, 1700–1789, historian Antonio Bly details runaway slave advertisements in some 400 newspapers in Connecticut, Massachusetts, New Hampshire, New York, and Rhode Island placed by over 5,000 owners of 3,600 runaways (3,200 in Massachusetts alone). The vast majority of them mention the possibility of escape by water. A typical one from the New England Weekly Journal on June 6 of 1732 reads:

“Ran-away from Mr. Nathan Cheever a Negro Man Servant named Portsmouth. Note, said Negro has been used to go in a Boat, and ‘tis tho’t will endeavor to get off to Sea; therefore all Masters of Vessels and others are forbid entertaining him, as they will answer it in the Law. He plays upon a Violin & is suppos’d to have one with him. Three Pounds Reward.”

Thanks to the Island’s leading place in the global whaling industry, Martha’s Vineyard was in a position to play a role in more than a few escapes. There are 16 documented cases (thus far) of fugitive or former slaves passing through the Island between 1728 and 1858. These include John Saunders, who brought Methodism to the Island in 1787, and Josiah Henson, who supposedly inspired the title character in Harriet Beecher Stowe’s Uncle Tom’s Cabin and who spoke at the Tabernacle in Oak Bluffs in 1858. There were doubtless many other freedom seekers who passed through the Island who deliberately avoided attracting attention, especially after the Supreme Court’s Dred Scott decision in 1857 allowed southern bounty hunters to recover escaped slaves in the free states.

An even larger number of fugitives no doubt encountered Vineyarders at sea, in route to other ports. The difficult and dangerous occupation of whaling provided unheralded opportunity for black men – and a likely escape from slavery by water. One event was led by mixed race (Black and Wampanoag) Captain Thomas Wainer whose uncle, Paul Cuffe was the first whale captain of color. In 1799 a Maryland slave owner took out a newspaper advertisement offering a forty-dollar bounty for the recapture of an enslaved man and his pregnant wife the owner alleged Wainer had helped escape to Westport. He described the fugitive as;

“a Negro man named Harry, about 23 years old—thick and well set—of a dark complexion, with thick lips and full eyes. . . Harry has a notable scar on or near the outside of one of his ankles, occasioned by a burn, also is marked on or near the calf of one of his legs by the bite of a dog.”

The scarce but small details in the ad – that Harry had been bitten by a dog at some point and noting his scars – remind us that the past was inhabited by real people living real lives.

One who we know more about is John Thompson, who escaped enslavement from Maryland. Pursued by slave hunters he fled to New Bedford, and signed on to the whaling bark Milwood, captained by Aaron Luce, of West Tisbury. While the ship voyaged for two years the two men developed an unlikely friendship, which is detailed in the current (May/June 2023) issue of Martha’s Vineyard Magazine.

Maritime escapes from enslavement from and to New England require more research to shed light on this important and under-reported aspect of our history and to celebrate those who successfully sailed to freedom, those who tried and failed and those who helped in myriad ways.

Skip Finley is the author of Whaling Captains of Color: America’s First Meritocracy.