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More notable Harpswell Ancestors are available in Wheeler's History of Brunswick, Topsham and Harpswell.

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Michael Sinnett



Michael Sinnett was born in Wexford Ireland about 1730 and died at Orr's Island, Maine 15 Sept. 1800 at the age of 70 years. He and his wife, Molly Ward are buried in back of the old Congregational Church at Harpswell, Maine.

The Reverend Charles Nelson Sinnett, a direct descendent of Michael, published a fine genealogy on the family in 1910, titled MICHAEL SINNETT OF HARPSWELL, MAINE, HIS ANCESTRY AND DESCENDANTS. In the preface to that work, Rev. Sinnett attempts to trace the origins of Michael in Ireland. This search is found to be nearly impossible due to the destruction of all records of the Sinnett family when Oliver Cromwell's army swept through Wexford during the early 1600's.Prior to this destruction it appears that the Sinnetts were a titled and prosperous family that had roots in County Wexford going back to 1172.

After Cromwell defeated the opposing forces in Wexford the Sinnett family was stripped of its wealth and titles, all of its lands, and all records, public and private were destroyed. Even grave markers were destroyed in an attempt to deny the survivors a link to their past. Many were left homeless and became tenants under the new proprietors of the land.These are the circumstances in which we find the Sinnett families when Michael is born almost 100 years later.

The following history of was furnished by his grandson, Capt. James Sinnett, of Bailey Island, Maine and included in the SINNETT GENEALOGY.

"Michael Sinnett, at the age of fourteen years (circa 1744), was apprenticed to a glove maker. In those days a boy must get his schooling before he was fourteen, and then learn some trade. At the end of his apprenticeship, when he was twenty-one years old (circa1751), he went to Dublin for a short holiday.
Two or three of his neighbors or brother apprentices went with him. They may not have seen a ship or the ocean before, and it was perfectly natural for them to stroll along the wharves and admire the ships in the harbor. At some point in their wanderings they were invited to ride down the harbor on a departing vessel, supposedly to be allowed to return to shore with the harbor pilot, but when they reached the open sea they discovered that the government liberally paid every shipmaster who brought over such likely young men, that they might help settle the colonies. They were paid whether the young men came of their own accord or not. Notice was given when a ship arrived and any one who would pay the passage price could then make a choice among the new arrivals. The person thus bought, was required to work for his purchaser for a period of time in compensation. Joseph Orr of Little Sebascodegan Island, in the District of Maine, happened to be in Boston, Massachusetts when Michael arrived, and perhaps having thought about the need of another strong back to help in his wood cutting business, he paid the passage and returned to his island home with the young man. Michael spent his days helping the Joseph and his brother Clement clear their land and begin a settlement on the island. The Orr brothers had owned the island only five years when Michael arrived but already many of the trees on the point where Joseph had settled had been cleared and large gardens had been planted. A barn was eventually built for a cow, and the oxen used in hauling the trees to the shore. A small building was constructed to house the ice chunks that were hacked from the pond that was created when a stream was dammed nearby and a pier was built to facilitate the loading of the trees onto the Orr vessel. A garrison house was build between the house and the pier in case of attack by Indians and the point on which Joseph built had excellent views both north and south along the Merriconeague Sound or River as it was referred to at that time. If the garrison were attacked by water the boats or canoes would be easily seen and if it should come by land the defenders could slip out the back side of the blockhouse to the pier and escape in their sloop. Michael's indenture was most likely for five years. It is unlikely that he would have been allowed to marry before becoming a freeman and in April of 1756 he was wed to Mary Ward of Hingham, Massachusetts. Molly as she was called, was the sister of Clement Orr's wife Deborah. After his marriage and on the advice of Joseph Orr Michael and Molly took 100 acres of land on the Sheepscott River near Boothbay where he built a shelter and with a yoke of oxen, began clearing land in Hingham by taking passage on a vessel headed for Massachusetts Bay. During her absence an English man-of-war sailed into the Sheepscott and a press gang took Michael and some of his neighbors off to New York City to fight in the English Army. They marched to the Great Lakes and across to Quebec. Michael was present for the siege of Quebec in 1759 and continued to serve until peace was declared in 1763. The troops were discharged where they stood and left to find their own way back to their homes as best they could. Michael quite likely made his way back through the wilderness in company with others in the same situation. During his absence Molly had returned home to find Michael gone. Her neighbors informed her of the circumstances and Michael may have even been able to send her word that he was in good health and on his way to Canada. Never the less, Molly found she could not continue alone on the Sheepscott and she returned to her sisters home in Casco Bay to wait for Michael's return. Joseph Orr brought her household goods and Michael's tools back on his sloop. It is uncertain if Michael returned first to his homestead on the Sheepscott or to Orr's Island as Sebascodegan was now being called, but eventually he made his way to Joseph Orr's house and was reunited with Molly. The Sinnetts never returned to their Sheepscott home. He sold the land and used the proceeds to purchase 10 acres from Joseph Orr near Lowells Cove. In 1777, Michael built a house for himself in the vicinity of what is now the Charles Huff house. Michael most certainly became acquainted with Will Black, a descendant of a Scotch family which had also opposed Oliver Cromwell and been deported to America. Will had moved his family from Newaggin Island just to the south of Orr's and bought most of the lower end of the island from Beals Cove to the southern point from Joseph. There were also others moving onto the newly cleared land on Orr's. David Wheeler was a neighbor as was David Alexander. John Hannaford And the Barstow family and Robert Wier and James Wilson. Michael's days as a warrior however, were not over. He was a member of the company of Captain Jonathan Doyle of Harpswell during the Revolution. Michael died in December of 1800 at Orr's Island at the age of about 70 years of age . A letter from John E. Sinnett of Sacramento, California, included in the SINNETT GENEALOGY states that..."The house of ancestor Michael Sinnett stood on the west side of the road leading over Orr's Island, half way from the Dunning Orr place to William Stevens place. The house was moved to the other side of the road some years ago, and has been somewhat changed. My father, John Sinnett, remembered seeing his grandfather Michael Sinnett in the spring of 1800; he was then on his sick bed in his last sickness. My father told me that this house of ancestor Michael Sinnett was partly built of logs." The house was later owned by James Pye about 1910.



Joseph and Clement Orr


Joseph Orr, so it appears, was the sole owner of Little Sebascodegan Island when it was purchased. His brother Clement did not own any of the land until 1760, when Joseph deeded the entire island to him. However a deed dated February 1762 states Joseph sold land at Beals Cove to William Black. It also appears that the title to the island was a bit confused even in it's origins. On March 20, 1748, Joseph purchased the what appears to be all of the island, from the heirs of William Tailor and/or Elisha Cook of Dorchester and Boston respectively. (York County Records).  

The deed of Elisha Cook is referred to as an "Indian Deed". Joseph neglected, however, to secure the signature of one of Tailors heirs, the wife of Rev. Mather Byles. of Boston. She placed a claim and on 22 July 1760, Joseph set off one tenth of the island for her in return for a quit claim deed to the remainder. According to the Orr Genealogy by C.N. Sinnett, Joseph then deeded all of the island [or all of the island that he owned] to his brother Clement as a life estate, and to Clements heirs after him.

  In the case of the death of Clement's heirs, the estate would revert back to the heirs of Joseph. The deed was dated 16 October 1760 (less than one month before Joseph was married). There are however, at least two deeds after that date in which Joseph Orr sells property on the island. Both are dated 1762 and are to William Black (Cumberland County Records Book 8 pages 171 and 183. One of them makes reference to "...Land of David Wheeler...".

  Another deed, dated 9 September 1785, is to Joseph Orr from Benjamin Jaques the heir and brother of Richard Jaques. (Richard bought 100 acres in 1743) In this deed Joseph buys 100 acres of Little Sebascodegan Island for 10 shillings. This deed seems to cover land that Joseph already owns per previous transactions and is recorded in Cumberland County book 121, 19 June 1786 (Note that the price paid is extremely small). I suspect that Benjamin Jaques had a shaky claim but Joseph decided it was easier to clear the title for a small sum than to let it continue. Joseph didn't marry until 1760 when he was 49 years old.



Samual Eaton


         Rev. Samuel Eaton Was the son of the first pastor; born in Braintree, Massachusetts, educated at Harvard College and by the advice of neighboring ministers, invited to become his father successor. Up until 1820 he was the only college educated man in the town.
During his college courses he had taken medical lectures, and also became somewhat conversant with the law, so that he was able to exercise great influence over the whole community. For many years almost every will made in town was said to be in his handwriting. He was a man of fine personal appearance and for years his tall figure, with powdered wig and cocked hat, full skirted coat, knee breeches and silver buckled shoes, was seen at college commencements and other notable gatherings.

          He lived at a time when history was making fast, and during the War of the Revolution was an ardent patriot, and exerted all his ability in the cause of his country. In the struggle of 1812 he was in the minority, and bitterly opposed the embargo, and the ensuing war. Preaching about this time in Freeport, he began his prayer thus; "Lord, Thou has commanded us to pray for our enemies and we will commence with Tom Jefferson, if he is already beyond Thy mercy.”

           His wide knowledge, ready wit, and good judgment gave him a position of influence , and  it is said that it was largely through his efforts that Bowdoin College was located in Brunswick, other neighboring towns bidding for that privilege. He was President of its Board of Overseers for a time and a member for many years.

            His fondness for children is indicated by his interest in their welfare, and the regular “catechizings” at the different schoolhouses where morality was never separated from religion, and where the practical duties of life were taught as well as religious and doctrinal creeds.

            He had a logical mind , good temper and fearless independence, qualities that would mark him as a leader of his times. He was never married and died at the ripe age of eighty-five. He nieces and nephews were honored citizens of the town and passed on some of the sterling qualities which make “Parson Eaton” a man of true worth, burning zeal and remarkable power.


Elijah Kellogg

                Elijah Kellogg was born in Portland, May 20, 1813. He was named Elijah after his father and spent his youth on the countryside around Portland and Gorham. He became familiar with sailing craft and spent many hours on the waters of Portland Harbor

He later attended Bowdoin College and became familiar with Harpswell and the Islands. He was so taken with the land and inhabitants of the town that he promised them when his Theological Studies were over he would return and become pastor.

            He apparently was well liked as a resident and well respected as a minister, for many came from the surrounding islands and pinisulas to hear him preach.

            He was also a prolific author, writing better than twenty works of fiction feachering Harpswell settings which boys and girls the world over enjoyed.

His writing kept him away from Harpswell while other preachers administered to the town but he remained “our minister” regardless of who was in the pulpit. He returned to Harpswell for the last ten years of his life.

 The church at Harpswell Center bears his name in memory of his service. And a monument stands in front dedicated to his memory.

            He died in Harpswell, March 17, 1901





William Cundy










Will Black

County of York
These may certifie whome it may concern that I John Shapleigh of
Kittery doe release and for ever set free one Negrroe man commonly
called Black Will which was formerly Maj. Nicholas Shapleighs now in
my possession I doe by these presents release and for ever set free
from me my heires Executer Administrater and from all persons
whatsoever laying any Lawfull Claine to or right to him Witness my
hand Kittery 13th Feb. 1700/.
John Shapleigh York ss/ Kittery March 21 1700/.
The above named John Shapleigh personally Appearing before me ye
subscriber one of his Majestys Justices of ye Peace in sd county of
York Acknowledged in this Instrument of Release, to Black Will therein
named, to be his act and deed/
Jos; Hamond
A true copy of ye above release with ye Acknowledgement
thereofTranscribed and compared this 2nd April 1701.


Legend and rumor have over the years become fact in many of the source books and it has been said in these histories that "Black Will" as he was known was a former slave of Nicholas Shapleigh of Kittery, in the district of Maine, and that he was given his freedom for having saved Shapleigh's life when they were shipwrecked.
Another rumor in the Black family was that the first Black in the line was a stowaway on a ship headed to America and after being
discovered by the ships Captain, he was told he was to be sold for the price of his passage upon reaching America. A couple named Black were passengers on the vessel and they felt sorry for the young man. Reaching the colonies, they searched out the authorities and paid the passage which entitled them to his services of for seven years. At the end of his indenture, the young man bade his benefactors good bye and set out on foot for the district of Maine. But not before he took their last name for his own in remembrance of their kind treatment of him. His first name was not recorded. Legend also says that "Black Will" was the first settler on Newaggin (Bailey) Island. However, evidence suggests that it was actually Black Will's son, William that made the move from Kittery to Casco Bay. Regardless of his race, country of origin, or exactly which one was the first on the island, a suitable and uninhabited place to live was found on Newaggin (Bailey) Island in the town of North Yarmouth in the District of Maine about 1727, where he built a cabin and resided quietly for some thirty years. (North Yarmouth eventually split into several smaller towns. Newaggin Island became part of the town of Harpswell when it was incorporated in 1758.) William Black, the son of "Black Will", assumed squatters rights to Newaggin. The ownership is acknowledged in the Act of Incorporation of the town of Harpswell at Harpswell Court in 1758. The island is referred to as "Will's Island". Throughout the Indian wars of that time period there is no record that Will or his family ever had to leave the island despite attacks on many other nearby outposts in the area. The channel between Bailey and Orr's Island is named Will's Gut, a gut being an old English word meaning an area of swiftly moving

In February of 1762, William Black (son of "Black Will") buys from Joseph Orr, most of the south end of Little Sebascodegan (Orr's) Island consisting of one hundred forty four acres, for one hundred and seventy two pounds. In September of 1762 he purchases all of acres) for thirty five pounds, nine shillings, four pence. The fact that William could afford to pay for that much land, in cash, doesn't support the popular perception that the family was poor and of little means. In 1777, he also purchased, for eighteen pounds, sixteen shillings, six pence, in partnership with Josiah Clark, "...equal parts of the two islands in or near Casco Bay called ...Capt. Parker's Island (now called Ragged Island) and Sagwin Island". The fact that this purchase seems to have been an investment rather than for a place to live indicates that Will may have had money to spare at that time and was not the destitute pauper history has made him out to be. It may be that he had been paid for his claim to title of Bailey Island and that he was not "driven" away by Timothy and Hannah Bailey. Deacon Timothy appears as a witness to the February 1762 deed between Joseph Orr and Will Black. In 1795 William Black buys from John Blake, nine and one half acres, for ten pounds, two shillings, eight pence. This land bordered on land owned by David Wheeler, Michael Sinnett and William Black. Between 1805 and 1807, an Elizabeth Meyer, calling herself the daughter of William Black, sells 23 acres on Orr's Island to Stephen Sinnett for one hundred twenty-six dollars and fifty cents, and all interest in an island in Casco Bay called Parker's Island or Ragged Arse Island containing about 70 acres to James Sinnett for fifteen dollars and twenty-five cents.


Capt. David Perry Sinnett
1843 - 1913

David Perry Sinnett has been credited by maritime authorities, such as Howard Chappelle in "American Small Craft", with having built the first vessel ever to use the strip plank method of construction.

Sinnett was a fisherman, boat builder and resident of Bailey Island when, in 1877, at about the age of 33, he began building a few two masted, lapstrake vessels called Hamptons. The design had originated in Hampton, New Hampshire and these boats were popular with the inshore fishermen of the day. Sinnett decided to square off the stern of this double-ender as an experiment.

Shortly after Capt. Sinnett began his square stern experiments. a local fisherman, Thomas Lubee, asked if the Capt. could built a square sterned, smooth hulled Hampton for him. Sinnett worked up a model and began gathering the stock. He built this vessel of wood strips, one and one half inch by one inch, nailed one on the other and put in ten pairs of steam bent timbers. This was the first smooth seamed, strip built Hampton ever constructed. (It has been surmised that he began using strips in boat construction because of a shortage of clear pine planking. The strips could be salvaged from the formerly unusable scrap that was abundant around his shop from cutting planks for previous boats). These sea-worthy vessels ranged from 21 feet to just over 30 feet with the most popular being 21 or 24.

About the turn of the century, power was added in the form of a one-lung Hartford or some other style of single cylinder make and break engine and by 1907 it was estimated that there were over 300 of these vessels in Casco Bay waters. Capt. Sinnett guessed that he alone had build 175 of them, and other Bailey Island builders had copied his methods as well. Prices ranged from about $5.00 to $12.00 per foot and Sinnett figured he could build a 20 footer for $100.00.





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Copyright 2005 Gerry York