Blacks were sold in Portsmouth along the harbor as early as 1645.

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A story on Black Will Researched and Written by Mario de Valdes y Cocom.

Some records state that Will Black settled on Bailey Island around 1739. It seems more likely that this was Will Black Jr and Will Black lll (who would have been between 19 and 23 years of age). It appears impossible to know which William setttled on Bailey's Island and which removed to Orr's Island. 


In the census records (1790, 1800 and 1810), I can find no record of anyone named Black even living in Harpswell until 1820. However, I have documents of land purchases made by the Black family before 1820 .

Primus Shapleigh of Auburn may have ties with a Primus Shapleigh who was freed from slavery when Captain John Shapleigh of Kittery, Maine

He was Auburn's first black settler

A Brunswick, Maine, marriage is found between Prime Chapley and Mareny Blake on February 13, 1793.

It is suspected that Mareny Blake was a descendant of Will Black or Black Will. Enter Captain John Shapleigh again who had freed Will Black or Black Will. The Blacks of the Kittery area had some children recorded there, but ultimately moved to what is now Bailey's Island and settled. Without good title to the land; they were soon displaced to Orr's Island. Some of the Black family in the area gradually changed their name to Blake.

There has been some evidence uncovered that Mareny and Lorania/Lorane/Lorene Blake were sisters. Perhaps Primus and Mareny were to have four children by the time of the 1800 census in order to have a household of six (although other relatives might have been included in the household to reduce the number of children). Perhaps Mareny died and Primus married her sister, Lorania by the time the 1813 deed was signed. Although there is a lot of conjecture here; a reasonable scenario could be developed to support the theory.


Deacon Timothy Bailey  Deacon Timothy moved from Hanover, Massachusetts, to Bailey's Island, Harpswell, Maine which was named for him, about 1750, accompanied by his wife and children.

Timothy was rather dissipated when the Indian Wars came on, at the time of the Means massacre, the garrison at the upper end of Short Point, Bailey's Island, was built to protect the people from the Wild Savages. In those days three guns were fired in succession to let the people know that Wild Savages were coming. Benjamin Curtis used to get drunk and fire away right and left, giving so many false alarms that at last, the people paid but little attention to them.

On the thirtieth day of September 1753 the church of Hanover, at his desire, voted Brother Timothy a dismission to qualify him in a regular manner to be a member of the Second Church going to be formed in the Second Parish of North Yarmouth, Maine (Harpswell was then a part of North Yarmouth).

Timothy was probably the first Deacon of the Congregational Church at Harpswell, Reverend Elisha Eaton, the pastor, boarded with him for a part of the year. Captain Bailey, for he is thus styled in the old records and was so addressed by the people of his day, bought the whole of what is now Bailey's Island, of a land Proprietor at Freeport, Maine, and it was then called "Proprietor's Land." Will Black was living on the Island when Captain Timothy came there, and was no doubt a "squatter?"

It has been said that Timothy was despised by the local native American tribe1. The Abanaki set him out to sea without oars and he came ashore in Wiscasset which is where he spent the remainder of his days.

Timothy died when is not known, at Harpswell. He is buried at Harpswell, Center, in the southwest corner of the cemetery, just back of the old Congregational Church.

[Sources: Walter Merryman of Harpswell, Maine, by Reverend Charles Nelson Sinnett. The Baily Family in Massachusetts and Maine by Reverend Charles N. Sinnett. Bailey Genealogy edited, by Hollis R. Bailey]

Hannah Curtis  Bailey Island originally was called Newwaggin. Prior to 1683, Orr's and Bailey Island were designated as "The Twins." Black, a trader from Kittery, Maine, is said to have been the first settler and built a comfortable home on the shore of picturesque Mackerel Cove for himself and his family. The family had resided at the island quietly for some 20 years. The son, Will, filed claim and received title to the entire island which thereafter became known as "Will's Island,"

Meanwhile, however, Hannah became the second wife of Deacon Timothy Bailey of Hanover, Massachusetts. A very enterprising woman, she, thanks to influential friends, procured for her Deacon, an appointment to the parish in North Yarmouth. She then decided that Will's Island was the most desirable place to establish a home. The Baileys purchased the island about 1750 from the North Yarmouth Land Proprietors for the price of one pound of tobacco and one gallon of rum.

This transaction legally discredited Black's claim, and he moved his family to Orr's Island, over the narrow strait, which immediately thereafter became known as Will's Strait.

Hannah and Timothy, meanwhile built a home at the north end of the island which now bears his name. His house was located near the garrison house or fort which stood on the shore of what is now known as Garrison Cove. He was very friendly with the Indians, especially Chief Mingo1. Hannah died after 1751, at North Yarmouth.

Besides the Blacks and the Baileys, other early settlers at Bailey Island included the Merrymans, Alexanders, Sinnetts, Johnsons, Gardners, and Orrs.

[Taken from: Bailey Genealogy edited by Hollis R. Bailey.]

From THE BRUNSWICK RECORD, Brunswick, ME., June 17, 1965, article by Dale S. Davis:

"Until 1809 Bailey people were buried mostly on nearby Orr's Island or across Merriconeag Sound on Harpswell." That year the 18 year old son of David Johnson drowned off the island. David buried him near his home, "diagonally across the present Route 24 and invited his friends to use adjacent land in a similar manner, thus establishing the cemetery. Later the Merriman, Stover, and Orr families gave additional lots for the same purpose. At the time they made one interesting stipulation: only natives could be buried there. They defined a native as one whose grandfather had been born on Bailey."

The Lane Scrapbooks by Beth Anne Bower The history of the African American settlement at Malaga Island, Maine, is a tale of a struggling but viable community treated dishonorably by government and commercial interests. Malaga Island is located near the mouth of the New Meadows River, close to Phippsburg, Maine. Although some sources suggest that Malaga was first settled in approximately 1720 by Will Black, an African frontiersman, it is certain that adjacent Horse Island was bought by former slave Benjamin Darling in 1794, who subsequently settled with others of African descent on Malaga Island.


In August, 1776, a committee was appointed to petition the continental Congress for some remuneration for the losses sustained by the people in the cause of American liberty; the petition was presented by Samuel Freeman.' The application was not successful ; having been rejected on the ground that all the towns on the coast being liable to similar visitations, it would be unsafe to establish a precedent which might embarrass the future operations of government. At the same meeting a committee consisting of Joseph Noyes, Enoch Moody, Daniel Ilsley, and Richard Codman, together with the selectmen of the town, was raised, to adjust and liquidate the accounts of the losses sustained by the fire. The committee, after a careful investigation, ascertained the losses to amount to fifty-four thousand five hundred and twenty-seven pounds thirteen shillings.1 The town did not sit down quietly under these losses; they applied repeatedly to the national Congress, and the State Legislature, and at length sought abroad for relief which in the embarrassed state of the country they could not obtain at home. After hostilities were over, they sent earnest appeals to the people of England, Ireland, and France, in 1783, and employed the services of Dr. Franklin and Gov. Pownal to give them effect; but all in vain, we have no evidence that anything was ever realized from those applications 2 At length however, in 1791, after having long and in various ways besieged the hearts of the members of the General Court, they obtained a grant of two townships of land, each six miles square, situated in the county of Somerset, and now called Freeman and New Portland