Searching for the first deeds for Bailey Island in Harpswell, Maine

I am searching for the deed/acknowledgment/contract, whereby Timothy Bailey of North Yarmouth receives ownership of Capenewagon Island aka Will’s Island aka Bailey Island in present day Harpswell.


Will Black of Berwick had moved onto the Island in 1727 with his wife and family and took up residence without benefit of ownership.


In 1733 the “Committee for the Resettlement of North Yarmouth”, divided up some of the islands in Casco Bay for themselves. William Dudley, one of the members of the “Committee” and a member of the Governors Council as well as being the son of former Governor Joseph Dudley, received a deed for Capenewagon/Bailey Island. Dudley died in 1743. He did have children and you would think that ownership would fall to them. But…


In about 1742, the Deacon Timothy Bailey and his second wife Hannah Curtis became interested in residing on Capenewagon Island. Most histories record that Timothy bought the island from “The Proprietors  and settled on the Island in 1742 although Will Black who had lived there since about 1727, retained his residency until at least 1756 - 1758 (17 more years). Why did he not buy from an heir of William Dudley?


(Contrary to popular belief, I do not think this William Black was the one forced to move to Orr’s Island by the Baileys. I believe, per James Sinnett in the Sinnett Genealogy by CN Sinnett, that William and his wife Elizabeth “were the first to die and be buried on the island” I suspect that their son William is the one who was asked to leave after his parents died.)


At any rate,  it appears that Timothy did not actually buy the Island from "The Proprietors" until  c.1758" and the popularly cited price for the island was two jugs of rum and a bale of beaver shins. I would dearly love to see primary data for that transaction.


(Several written histories only say Bailey bought from ”The Proprietors” . I am unsure if this refers to the Pejepscot Proprietors, who may have had a tenuous claim to the islands south of Brunswick or to others.

Were there North Yarmouth Proprietors?


Were they different than the Committee for resettlement in North Yarmouth?


Where do these records reside now? I have heard the Pejepscott records are at Maine Historical Society but are records from North Yarmouth there as well or are they elsewhere. I heard a rumor that the might be in the Essex/Peabody Museum? Does anyone know?


In deeds recorded in Cumberland County after 1760, some deeds for Bailey Island refer to the “Deed of Division” Which I take to mean the first deed where Timothy Bailey/Bayly/Baily divides the island in two with his brother in law Benjamin Curtis but the reference I have seen only says it can be found in the papers of  “The Proprietors”. 

What Proprietors and where are the records?

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