EARLY ROADS OF THE HILLTOWNS One of the early factors in bringing Middlefield more closely in touch with the outside world was improved transportation. Soon after the War of 1812 the increasing travel and business between the Connecticut Valley towns and Pittsfield and the west led to a demand for a better thoroughfare from Springfield. Besides the Third Massachusetts Turnpike reaching Pittsfield by way of Northampton, Worthington and Peru, the most used road was the Hampden and Berkshire and Housatonic  Turnpikes, chartered in 1826, reaching the same point by way of Blandford and Lee. Both of these routes traversed steep hills, and both were notorious for accidents to stagecoaches.

As early as 1818 it had become known that an easy grade through the Berkshires lay through the “Pass of the Westfield” at the northern end of Mt. Gobble in Chester,–where the three counties of Berkshire, Hampden, and Hampshire meet, and along the river to the mouth of Factory Brook in Middlefield.  A preliminary survey of this route for a railroad was made at an early date, but such a proposition seemed visionary, and the building of the Pontoosac Turnpike through this valley appeared much more feasible. “Turnpikes of New England-Wood”

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