Like his father, James Endicott was an innkeeper in Canton. He first married Esther Clapp. Esther was born on 10 February 1699. She was the daughter of Ezra and Experience Clapp. Esther and John Endicott were married on 26 November 1723. Between the years 1726 and 1741, the couple produced six children, including three boys and three girls.

• Ebenezer, was born on 10 July 1726. Nothing has been found about his life and he may have died as a child.
• James, was born on 10 July 1728. He only lived for nine months and died on 27 April 1729.
• Hannah was born on 12 April 1730.
• Esther was born four years later on 14 March 1734.
• James was born on 17 August 1738. It was a very common practice in those days to use a name more than once if the first child with the name had already died. James played a significant role in the American Revolution.
• The final child was Sarah and she was born on 10 August 1741.

Esther Clapp Endicott had led a very full life and she died on 11 July 1750 at the age of 51. Not wasting any time, James Endicott married again just six months later on 9 January 1752. The new wife was a widow herself named Hannah Tilden Lyon. They had no children but were together for 17 years. James Endicott died on 21 October 1768 at the age of 72. Like his father, Gilbert Indicott, James was buried in the Canton Corner Cemetery.