Olive Bailey was born in Salem, NH in 1772, the daughter and youngest child of Jonathan Bailey and Martha Clark.[1][2] Olive was still a teenager when her parents moved her family to Westminster, VT in the mid 1780’s.
It was there (Westminster, VT) that Olive met and married Squire Chaffee, in about 1787. Squire had lived in Westminster, VT since he was about 10 years old, his father being one of the first settlers (1750s) and official surveyor of that town. Olive and Squire had three or four children, of whom we know the following:
Squire Chaffee was taxed as a resident of Hadley, Saratoga County, NY in 1801 and 1802.[3][4] Squire and Olive Chaffee were living at Hadley, NY on 15 June 1806 when they acknowledged the distribution of the estate of Olive’s brother, Jonathan Bailey, Jr.[5]
Squire and Olive later went to Vincennes, then in Knox (now Vigo) County, IN where Squire Chaffee served as a Private in Jordan’s 1st Regiment, Indiana Militia during the War of 1812. The Chaffee genealogy claims Squire and Olive afterwards went to Venango County, PA and died there, but no records could be located to confirm this, although their daughters/grandsons settled in Venango and bordering Crawford County, PA, but not until the 1830s.
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