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The land near the river was clear of trees due to burns by the Indians, and covered in nutrient-rich river silt from both floods and glacial Lake Hitchcock.
Just south of the Westfield River, Cable and Woodcock constructed a pre-fabricated house in present-day Agawam, Massachusetts (at modern-day Pynchon Point.) In 1636, Pynchon led a settlement expedition to be administered by the Connecticut Colony, which included Henry Smith (Pynchon's son-in-law), Jehu Burr, William Blake, Matthew Mitchell, Edmund Wood, Thomas Ufford, and John Cable.
He advised Springfield's settlers to move to the eastern side of the river, between the Chicopee and Mill Rivers.
This site was slightly less advantageous for farming because of its prominent bluffs and hills.
By founding Springfield, Pynchon positioned himself as the northernmost trader on the Connecticut River.
Near Enfield Falls, he erected a warehouse to store goods awaiting shipment, which is still called "Warehouse Point" to this day, located in East Windsor, Connecticut.
Springfield flourished as a trading post and agricultural center until 1675's King Philip's War, when a coalition of Indians laid siege to Springfield and later burned it to the ground.
On reaching what would become Springfield, Mason threatened the Pocumtucs with war if they did not sell their corn at "reasonable prices." The Pocumtucs capitulated and ultimately sold the colonists corn; however, Mason's violent approach led to the natives' deepening distrust of the English.Before leaving, Mason also upbraided Pynchon publicly, accusing Pynchon of sharp trading practices and of forcing the Pocumtucs to trade only with him because they feared him.(The three southern Connecticut Colony settlements were surrounded by different tribes than Springfield, i.e.the more warlike Pequots and Mohegans.) Ultimately, in 1640, Pynchon and the planters of Agawam voted to separate themselves from the other river towns, removing themselves from the jurisdiction of Connecticut Colony.Looking to capitalize on Springfield's defection, the Massachusetts Bay Colony decided to reassert its jurisdiction over land bordering the Connecticut River, including Agawam.