Captain Stephen Fay was born in Westborough, Massachusetts, in 1715 to John and Elizabeth (Wellington) Fay. He married Ruth Childs in 1733; they would have ten children. The couple settled in Hardwick, Massachusetts, but moved to Bennington, Vermont, in 1766 where they ran a tavern called Green Mountain House that later became more famously known as the Catamount Tavern. Fay quickly became swept up in the turmoil surrounding competing claims of New York and New Hampshire to the region that would become the state of Vermont. The tavern hosted frequent meetings of Ethan Allen's Green Mountain Boys and Fay and several of his sons served in the American Revolution. Stephen Fay died in 1781, aged 66.
In 1772, Stephen Fay purchased Peg Bowen (1742-n.d.) from Charles Porter Phelps of Hadley, Massachusetts. Peg worked for Fay in the tavern for six years, until Fay sold her back to Phelps in 1778 where she remained until she gained her freedom and departed in 1782.
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