Simeon married first Mercy Cook, widow of _____ Walker,[1] and after her death he married her sister, Jane Cook. He and Mercy had 11 children; he and Jane had a further 8 children.
From a biographical sketch:
[Simeon Tryon] settled in that part of Freeport which is now called Pownal, at an early date in the town's history, and, purchasing the farm which is now owned by his son, Andrew J. Tryon, resided here the rest of his life. The improvements are the result of his labor and industry, and the present brick house was erected by him in 1806 from material manufactured upon the farm.
Simeon Tryon was well and favorably known in his day, and acted for many years as justice of the Peace. He conducted farming with energy and prosperity during the active period of his life, and died August 7, 1844, aged sixty-five years and ten months. He was twice married. His first wife, Mercy Cook, who was born in Litchfield, Me., died March 24, 1825; and he wedded for his second wife Jane Cook, who was also a native of Litchfield, where she was born in the year 1800. Simeon Tryon reared a family of nineteen children …[2]
From a history of Pownal:
The history of Mrs. Simeon Tryon who later came to Pownal with her son [Simeon Jr], is very interesting, and we only regret that lack of space prevents our giving it in full. Her husband, a graduate of Yale in 1769, was first lieutenant in a New York regiment in the Revolutionary War, and later he served as surgeon at West Point where he died in 1778 during an epidemic of small-pox. To her friends here, Mrs. Tryon would frequently relate her last conversation with her husband, held through an open window in the hospital where he was confined. After her husband's death, the house where she lived in Fort Fairfield was burned by the British, and she was left homeless with her three children. She had two brothers and one sister in Gorham, Maine. She decided to go to them, and with one of the brothers who came for her, she made the long journey in a sleigh or sled, during the cold, bleak winter. After living for some years in Gorham, she came to Pownal with her only remaining child, Simeon Tryon. He at once won the respect of his townsmen. He filled many public offices and received the title of Squire. In 1802, he married Mercy Cook and, after her death, her sister, Jane Cook. They were daughters of Samuel Cook, a Revolutionary soldier of Litchfield, Maine, and on their mother's side they were descended from a member of the Plymouth colony. He built in 1806 from brick made on his own land, the fine house which is still standing. Of the nineteen children of Simeon Tryon, Samuel and Jackson became identified with the history of Pownal. Descendants now living here are Augustus Tryon and Mellen Tryon.[3]
NOTE: Many of the available records naming Simeon are the birth records of his children.
Connecticut, Church Record Abstracts, 1630-1920 for Jane Tyron, Volume 104, Sherman (ancestry.com) "Tyron, ___ wid. her son, b. 1778." and "Simeon, dau. of wid." Note that Sherman is part of New Fairfield.
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DNA Connections
It may be possible to confirm family relationships with Simeon by comparing test results with other carriers of his Y-chromosome or his mother's mitochondrial DNA.
Y-chromosome DNA test-takers in his direct paternal line on WikiTree: