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In 1635, he commissioned a scouting expedition led by John Cable and John Woodcock to find the Connecticut River Valley's most suitable site for the dual purposes of agriculture and trading.The expedition traveled either across the inland Bay Path from Boston to Albany via Springfield or, equally likely, along the coast and northward from the mouth of the Connecticut River.
Springfield, Massachusetts was founded in 1636 as Agawam, the northernmost settlement of the Connecticut Colony.
Cable and Woodcock found the Pocomtuc (or perhaps Nipmuck) village of Agawam on the western bank of the Connecticut River.
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.
This site was slightly less advantageous for farming because of its prominent bluffs and hills.
In 1636, Pynchon's party purchased land on both sides of Connecticut River from 18 tribesmen who lived at a palisade fort at the current site of Springfield's Longhill Street.
Springfield also sits on some of the northeastern United States' most fertile soil.
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.
Pynchon selected a spot just north of Enfield Falls, the first spot on the Connecticut River where all travelers have to stop to negotiate a waterfall 32 feet (9.8 m) in height, and then transship their cargoes from ocean-going vessels to smaller shallops.
By founding Springfield, Pynchon positioned himself as the northernmost trader on the Connecticut River.
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 natives refused to sell their corn at market prices, and then later refused to sell it at what Pynchon deemed "reasonable" prices.