These letters offer valuable insights into Pynchon's personal life, his views on trade and commerce, and his relationships with other colonists and Native Americans.
Pynchon was a man of peace and also very business-minded — thus he advocated for friendship with the region's natives as a means of ensuring the continued trade of goods.
Roxbury — originally named "Rocksbury" for its rocky soil — was a poor site on which to farm in comparison to the fertile Connecticut River Valley.
On the banks of the Connecticut River, in an area called "Agawam" (ground overflowed by water) by local Native people, Pynchon and his collaborators found such a place.
Perhaps most strategically of all, Pynchon's settlement was located equidistant to the New World's (then) two most important ports, Boston and Albany, with Native roads already cleared to both places.
As noted above, after disagreements with Captain John Mason and later Thomas Hooker about how to treat the native population, Pynchon became disenchanted with the Connecticut colony.
After Pynchon's return to England, his son John extended his father's settlements in the Connecticut River Valley northward, founding Northampton, Westfield, Hadley, and other towns.
Since 1915, the Order of William Pynchon has been awarded to individuals who have "rendered distinguished service to the community" by The Ad Club of Western Massachusetts.