John Pynchon's life illustrated the opportunities and gains that attracted English settlers to the New England frontier. He was born in Springfield, Essex County, England, and came to New England in 1630 with his father, William Pynchon (1590-1662). His family first settled in Roxbury, Massachusetts, and moved west in 1636 when his father founded Springfield, which was part of the Connecticut Colony until 1638. Springfield originally included lands that today make up all or part of several towns in Massachusetts and Connecticut. It was the northernmost trading post of the Connecticut Colony and was seated on major trading routes, including the Connecticut River. In 1652, William Pynchon returned to England, leaving the management of Springfield and the family business to John, who was then only twenty-six. John expanded his father's holdings, establishing trading posts to the west, at Westfield, and to the north at Northampton and Hadley. He also expanded his business interests to include Boston and Barbados, and directly shipped Connecticut River Valley furs to England on the company's own ships. John represented the town of Springfield in Boston, was captain of the Springfield militia, and fought in Metacom's (King Philip's) War (1675-1676). By the time he died, he was the wealthiest and most powerful landowner in western Massachusetts.