Nathan Bailey was the second child and first son of Joseph Bailey and Martha Boynton, born in Tewksbury, MA in 1735.[1] He and his brother Richard Bailey married sisters, then both migrated from Massachusetts to Maine, before 1766 in the case of Richard, and not later than 1770 for Nathan. Nathan married Sarah Pillsbury in Newbury in 1757.[2] Note that his sister Martha (like his brother Richard) also married Pillsbury siblings of Sarah.
On 6 Apr. 1758, Nathan received an inheritance of 26 pounds as a result of the decease of his paternal grandfather, his uncle John Bailey being the Executor.[3]
At the time of the family's settlement in Maine the area was still an undeveloped frontier, just beginning to be settled with the establishment of the new Lincoln County in 1760. The roads were little more than blazed bridle paths, and the rivers served as the main means of travel through miles of forests. There were no schools or organized churches there yet, and a grandson of Nathan's recalled being told that lessons were taught to the children in a foreroom of the Bailey house, where the children used a pine shingle for a slate and a bit of charcoal as a pencil.
Nathan settled just north of his brother Richard Bailey's homestead on land which is now in Whitefield, but at that time was unorganized territory on the northern border of Pownalborough (now Alna), Maine. Nathan owned a tract of one hundred and thirty-three acres on the "Whitefield Plains", an area of rocky fields and gravel soil extending west from high banks above the Sheepscot River. Later blueberry fields and still later a commercial gravel pit, in the 1760s the area had the advantage of providing river access, and clear fields over the gravel soil, fronting stands of virgin forest. Nathan was a cordwainer (shoemaker), as he had been in Newbury, and farmed.
Nathan and Sarah had four sons, the two or three eldest born in Newbury, MA:
Nathan was recorded in Pittston, ME on the 1790, 1800 and 1810 censuses.
Nathan Bailey was a sergeant in the Revolutionary War in Capt. Scott's Company of Col. North's regiment of Massachusetts Troops, Maine then being still a part of Massachusetts. He served in the militia that retook a mast ship from the British on the Sheepscot River at Wiscasset in 1777, and was also in the Penobscot Expedition in 1779.
Nathan Bailey and his family were drawn to the teachings of the Baptist Church and on 6 January, 1788, "Nathan Baley, Deacon John Baley, and Mercy Baley" were among a small band of fifteen people who organized to form a Baptist Church. Three of Nathan and Sarah's four sons preached as Baptist ministers in the years to come, Joseph Bailey as minister of the Baptist Church in Whitefield for fifty-two years, with brother John Bailey as Deacon in the same church.
Nathan sold his land in Whitefield in 1795. After the sale of the homestead, Nathan and Sarah spent their remaining years in nearby Pittston, Maine, living with their oldest son, John. On 8 Nov 1819, his neighbor Samuel Palmer noted in his diary, "I go to Nathan Bailey's funeral, he died the 6th." Their stone in the Whitefield Cemetery is a memorial marker erected to the memory of Nathan Bailey and his wife; it is probable that they are actually buried in the John Bailey Family Cemetery in Pittston.[4]
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