Jonathan Taylor, Sr. (1724-1800) was born in Deerfield, Massachusetts, the youngest of five children. His parents were Samuel Taylor and Samuel's second wife, Mary Hitchcock. Jonathan married Lucy Hastings in 1744. Three of Jonathan and Lucy's six children died in infancy. The year before his marriage, Jonathan and his older brother Othniel cleared land in what would become the town of Charlemont, Massachusetts. The settlement was located in contested territory and early residents suffered from numerous attacks by Indigenous raiding parties that were often allied with French who at that time controlled Canada. In an effort to protect their families from attack the two brothers built Taylor's Fort, a fortified farmstead surrounded by a palisade, on the eve of the final French and Indian War (1754-1763.) In about 1760, Jonathan moved to a part of Charlemont that later became the town of Heath, Massachusetts, farming land he had purchased from Othniel. Jonathan Taylor died in 1800, aged 76. (George Sheldon, History of Deerfield (Greenfield, MA; PVMA, 1896), p. 337, 339.)
In 1746, Joseph Barnard credited Jonathan for buying a pair of shoes for Prince, who was enslaved by Barnard. That same year Jonathan borrowed three shillings from Barnard to pay "Sharp", a man of African/Indigenous heritage who was known as "Sharp Calab" and "Calab Sharp." In 1771, Taylor purchased a thirty-one-year-old enslaved man named Titus from his stepbrother Daniel Arms of Deerfield for 20 shillings. (Account book of Joseph Barnard, PVMA Library, Deerfield, Massachusetts; Healy, Allan, Charlemont, Massachusetts, Frontier Village and Hill Town 1765-1965 (Charlemont, MA: 1965.)
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