While no one is known to have lived in Chesterfield in the dangerous early decades, soldiers and explorers certainly knew and walked this land.
As noted earlier, Chesterfield (“Township #1”) was created in 1736 along with 3 other Connecticut River towns. This happened just after Winchester, Keene and Swanzey were created in 1733-1734 in the valley of the Ashuelot River. These towns were first known as Arlington, and Upper and Lower Ashuelot. Chesterfield’s rockier landscape was less appealing to the first settlers of Cheshire County.
But these three Massachusetts land grants established the first boundaries of Chesterfield – the south and east lines of our town.
Old Winchester (then called Arlington) had an inverted “L” shape which gave it both frontage on the Connecticut River and prime land in the Ashuelot River valley. It stretched all the way to the Connecticut and included the northern part of Hinsdale across from Brattleboro. The north line of 1733 Arlington is the same as today’s Chesterfield south line.