In the early commerce between the colonies of Massachusetts and Connecticut a popular route over the land was through the region now covered by Windham county. Remote from the sea shore, and possessing no navigable lakes or rivers, it was perfectly reasonable that this territory should be for a time overlooked, or rather that it should be passed by as a goodly land for the home-seekers in a new world to locate upon. Accessibility by water was to the first settlers an almost absolutely essential feature in any site chosen by them for the planting of a little colony. But we may well imagine that the fertile valleys and hills of this beautiful region, and the picturesque attractions of the future Windham did not long remain unnoticed. The land became known to the English about the year 1635. When, about that time, the early colonists began to traverse the hideous and trackless wilderness, on the way from Massachusetts to the Connecticut river, tradition tells us their encampment for the night was on Pine hill in Ashford. A rude track, called the Connecticut Path, obliquely crossing the Wabbaquasset country, became the main thoroughfare of travel between the two colonies. Hundreds of families toiled over it to new homes in the wilderness. The fathers of Hartford and New Haven, ministers and governors, captains and commissioners, government officials and land speculators, crossed and recrossed over it. Civilization passed to regions beyond but made no abiding place here for   more than half a century.

      On of the most indefatigable land speculators of that period was Mr. John Winthrop. In Massachusetts, in Rhode Island, in Connecticut and upon Long Island his tracks may be seen, as, first in one locality and then in another, he obtained title more or less perfect to the wild lands occupied by the Indians. Here in the territory now occupied by Windham county he was the first Englishman to receive from the natives a deed for an indefinite quantity of land. This conveyance beats date November 2d, 1653, and purports to have been given by James, sachem of Quinebaug, and confirmed by Massashowitt, his brother, and also to have been made with the consent, full and free ; of Aguntus, Pumquanon, Massitiarno, his brother, and Moas, and all the rest of the chief men of these parts; The confirmation by other than James was made on the 25th of the same month, the writings being witnessed by Richard Smith, Samuel Smith, John Gallop, James Avery and William Weloma