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Ann Sinclear's
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John's signature from his father's probate file in 1766
The prevailing spelling of this family's name in John's lifetime was "Cuningham."
John supposedly came with his parents and siblings to Boston in 1717 from Coleraine, Ireland. His father and uncle Archibald Lamond (another Scots-Irish immigrant) bought land to settle on in Leicester, Massachusetts, where there was a small Scots-Irish presence. They divided their jointly-owned "great farm" into three parts in 1742. Lamond had already settled on the northern part and Robert in the middle. John bought the southern third.1 He had just started a family, having a wife and child by then, so his house may have already been built there. His wife was also from a Scottish family living in Ireland.
The town of Leicester grew to the point that a second precinct was needed. When they built their meeting house, John was voted to a committee to receive claims against the town treasury for work done in 1745.2 He was elected constable in 17473, but apparently declined, another person taking his place. He apparently accepted the vote for him to be a fenceviewer in 1752. 4 Good fences meant no stray livestock. Leicester's second precinct was permitted to form itself into a separate town called Spencer. John was elected a selectman for Spencer at the first official town meeting on 14 May 1753 and again in 1754.5 He was also a tax assessor in those years, surveyor of highways for the "North Side" where he lived and tax collector.6 He was on the Committee of Correspondence for Spencer in 1774, a position similar to representatives of districts that later served in the state government after the Revolution.
In March 1783 John sold his homestead to his son Robert, probably with the agreement that Robert would take care of John and Ann, who were now elderly.
children of John Cuningham and Ann Sinclear (the years in the town records aren't double dated to reflect the change from the Julian to Gregorian calendars, so I've converted them for clarity):
i. Robert b. 25 March 1739/40
ii. John b. 9 February 1745/46
iii. Jonathan b. 6 June 1748
iv. David b. 6 June 1748
v. Nathaniel b. 16 March 1751/52
vi. William b. 11 November 1754
vital records sources: His marriage intentions and marriage are in the Leicester town records (familysearch.org images 112 and 121). His death date is on his gravestone in the Spencer Congregational Church cemetery and says he was "in his 80th year" (79 years old) when he died. Given that he died early in the year, he likely turned 80 in 1789, giving him a circa birth date of 1709.
1. Worcester Co. deeds, 15:42.
2. 2 Sept 1745, Spencer (as Leicester west parish) town records, p. 13 (not paginated), ancestry.com image 7.
3. 2 March 1746/47, Leicester town records, vol. A, pg. 4-5, familysearch.org image 15.
4. 23 Mar 1752, ibid, fenceviewer, p. 25, image 25.
5. 14 May 1753, Spencer town records, p. 30 (not paginated), ancestry.com image 15; 4 March 1754, p. 34, image 17.
6. 3 March 1755, ibid, image 21.
7.James Draper, History of Spencer, Massachusetts, from its earliest settlement to the year 1860 (Worcester:1860). Committee to oversee Spencer's contribution to covering the costs of the Continental Congress, 48; Committee of Correspondence 1775, 137, with Oliver Watson and Asa Baldwin