A view of Will’s Gut from Orr’s Island, looking toward Bailey Island and Water Cove. The channel between the islands bears the name of William Black Jr., an early settler of Bailey Island who lived on Water Cove. (TOM LUNDE PHOTO)

Rumor has it that a man called “Black Will” was the first nonnative to settle on Bailey Island. Those who have explored the matter further may have learned that a man called Black Will or Will Black moved to the island in the early 18th century; and that after Deacon Timothy Bailey purchased the island, Will Black relocated across the channel to Little Sebascodegan, now Orr’s Island. But even that information is misleading, given that there were several Will Blacks, and some important questions concerning the correct one remain: Where did he come from? Why did he choose this island over others on the Maine coast? Did he purchase the land on which he lived, or was he, as some have assumed, a squatter, unable to pay his way? While history presents some gaps and contradictions, a reasonable account may be made by combining Will’s experience with those of his better-known contemporaries.

William Black Jr. was born in Piscataqua (Kittery), Maine, in 1691, to a white mother and an enslaved Black father. The mother, Alice Hanscom, was 20 years old, and was considered by contemporaries to be “a woman of loose carriage.” The father, then 22, was called William or “Black Will.” He was a slave on the Shapleigh plantation. Nicholas Shapleigh, a wealthy English trader and shipbuilder, had taken Will to Maine from Africa when he was a child.

Well liked by the Shapleigh family, Will had privileges not granted to most slaves. He lived in his own house on Shapleigh land and earned money from work off the plantation. After Nicholas died in 1682, he became the property of Nicholas’ nephew John.

Because Massachusetts law forbade marriage between the races, Will’s boy, originally named Jonathan, became a ward of the town. He remained so until age 10, when his father, having saved 25 pounds from work he had done off the plantation, purchased 100 acres of land. Noting Will’s desire to be free and perhaps relieved to be cleared of financial responsibility for his son under Colonial law, John Shapleigh granted him his freedom in 1700.

“Black Will” thereupon changed his name to William Black. He renamed his son William Black Jr. and brought him to live with him on his 100-acre farm. Alice Hanscom subsequently became involved in yet another scandal, this time involving a married man named John Thompson, before dying young.

William Black Jr. learned from his father the necessary skills for becoming a respectable adult: working hard, paying one’s debts and contributing to the community. One lesson he learned the hard way was the obstacle that race posed, particularly when it came to marriage.

As the child of a white mother, Will Jr. was born free, but that freedom did not extend to choosing a mate. In 1714, he fell in love with a white woman, Elizabeth Turbet, and the two took up housekeeping on land he had purchased in nearby Berwick. When their relationship became known, they were charged with fornication, and Will was jailed. They then published their banns, but the local magistrate disallowed the marriage.

When their son, William Black III, was born in 1718, charges of bastardy were brought against them. Elizabeth received 20 lashes. Both parties would normally be whipped, but no record of Will’s punishment could be found.

Soon after that, Will Jr. moved his family up the coast to Bailey Island, then known as Capenawagen. Will built his cabin on Water Cove, near the strait that now bears his name. The distance from prying English eyes suited the family well. Unlike many other settlers, they maintained a good relationship with local tribes. By the time English authorities got around to assigning boundaries and land rights, Capenawagen was generally known as Will’s Island.

Enter William Dudley, son of former Gov. Joseph Dudley and a member of the Massachusetts House of Representatives from 1718-1729. Dudley was politically influential and known for his savvy in land investments. When the Committee for Resettlement was established in Boston in 1735, he set his sights on Will’s Island. He asked to be granted “the island upon which Black Will lives,” but received New Damariscove (now Haskell) by mistake. He went back to the committee and specified, “the island whereon said Black Will doth reside, commonly called Capenawagen.” An exchange of deeds was made the following year, seemingly without consulting Will. But Dudley never got to occupy the property himself. When he died in 1743, it was still considered “Will’s Island.” 

The next investor was Deacon Timothy Bailey, a Massachusetts man who had been called to the Second Parish Church in North Yarmouth (now the church at Harpswell Center). At the behest of his wife, Bailey bought Will’s Island, reportedly for “one pound of tobacco and one gallon of rum.” Given the nature of this transaction, it seems likely that the fee went to Will Jr. — or, through him, to the local sachems — rather than to Dudley’s heirs. The sale probably occurred around 1753, when Bailey assumed his post as first deacon. Still, when the town of Harpswell was incorporated five years later, “Black Will” remained the titular owner of “Will’s Island.”

Some have concluded that Deacon Bailey evicted Will when he bought Capenawagen, but the timing and other evidence suggests not. In 1762, Will Jr. died and was buried on his island, as was his wife, Elizabeth. Subsequently, Will’s son, whom C.N. Sinnett referred to as “Uncle Will,” removed across the strait to Orr’s Island, buying a large tract of land from Joseph Orr and paying for it in cash. Timothy Bailey served as a witness to that sale, suggesting that the two families lived on cordial terms.

Deacon Bailey died in 1785, leaving his property to his widow, Hannah, who lived another 30 years. Following Will’s departure across Will’s Strait, the island came to be known as Bailey’s Island. It was changed to Bailey Island in 1892, when the U.S. Postal Service shortened the address.

Sources for this article include the Harpswell Historical Society newsletter, winter 2015; “The strange saga of early settler Black Will,” by Richard Wescott, Harpswell Anchor, April 1999; “Lives of Consequence: Blacks in Early Kittery & Berwick in the Massachusetts Province of Maine,” by Patricia Q. Wall; “Slavery in Colonial Maine,” by Randolph Stakeman, published in Maine History, Vol. 27, No. 2, 1987; “History of Brunswick, Topsham, and Harpswell, Maine, including the Ancient Territory Known as Pejepscot,” by George Augustus Wheeler and Henry Ware Wheeler; “Genealogical and Family History of the State of Maine, Vol. 4” by George Thomas Little; and “Ancestor Thomas Bailey of Weymouth, Massachusetts and Descendants Who Wrote their Name Bailey,” by C.N. Sinnett.

Joann Gardner was an English professor at Florida State University for 39 years. Now a freelance book reviewer, poet and essayist, she divides her time between Bailey Island and Tallahassee, Florida.