By 1633, the Puritans of the Massachusetts Bay Colony towns of Newtown, Watertown, and Dorchester were agitating for new lands on which to accomodate their increasing numbers. Doctrinal schism played no small role in motivating some prospective emigrants, and the unsettled valley of the Connecticut River, west of the Bay Colony, beckoned. The Dutch and the Pilgrims of the Plymouth colony also desired settlements on the Connecticut, but it was from the Bay that the majority of Connecticut's first planters originated.
From Andrews, Charles McLean (1863-1943). "The River Towns of Connecticut: A Study of Wethersfield, Hartford, and Windsor". Johns Hopkins University Studies in Historical and Political Science, 7th ser., 7-9. Baltimore, Publication Agency of the Johns Hopkins University, 1889. LCCN 04007961
"This was the man [John Oldham] who, early in September, 1633, started out from the [Massachusetts] Bay with John Hall and two other companions to trade in Connecticut. Plunging boldly into the wilderness, so soon to be made historic by a more famous emigration, they pursued a winding intinerary, in order to take advantage of Indian villages where they might lodge at night. On reaching the valley they were hospitably received by the sachem, possibly the one who had already visited Boston, and on returning, carried back to that colony beaver, hemp, and black lead. Regarding the southernmost point reached by Oldham we have no information. The distance to Connecticut was reckoned by him as one hundred and sixty miles. Allowing for the necessary windings incident to a journey through a primeval wilderness, and supposing him to have reached for greater security the river at a point due west from the Bay, perhaps near Springfield, and then to have followed its course southward, the above impression which he received of the distance is easily explainable. That Oldham and his companions penetrated as far south as the then unoccupied sites of Hartford and Windsor is undoubted, and that he was the first white explorer of the lands farther south in the present Wethersfield township, further evidence gives good reason to believe."
"[In 1634]... there is some evidence of an exodus from Watertown to Connecticut. ... There has long been a tradition that a few Watertown people came in 1634 to Connecticut and passed a hard winter in hastily erected log huts at Pyquag, the Indian name of Wethersfield. Tradition is apt to contain a kernel of truth, and in this case further evidence seems to substantiate it. In case such a movement took place from Watertown, whether because of the decision of the Newtown people to remain, or independent of it, it is unlikely that Oldham would have failed of cooperation with the movers, if he was not actually an instigator of the plan itself. ..."
"[Oldham] was sufficiently acquainted with either route - overland or by sea - to have taken the journey without great inconvenience. ... With this then as our evidence, we venture the following historical sequence. Shortly after the September meeting of the Massachusetts General Court in 1634, Mr. Oldham led a party of eight adventurous men to the point reached by him on his overland journey in 1633, where he was impressed by the fertility and beauty of the river meadows and the fact of non-occupation by white men. Here huts were erected, the ground prepared and grain sown along the lowest eastern slope of the ridge, half a mile from the river, out of reach of the spring freshets. In the following spring Mr. Oldham returned to Watertown, and very likely his presence once more among the uneasy people instigated the petition which was presented by them to the court held in Newtown, May 6, 1635, asking leave to remove. A favorable answer was given to this, and Mr. Oldham accompanied a second band of settlers, some fifteen or twenty in number, who settled in Wethersfield, near the others, to the westward. We are without doubt warranted in the statement that of the three towns composing the Connecticut colony, Wethersfield was the first occupied by settlers and planters who became and integral part of the later community. ... The existing state of things [1635] is, then, a Dutch fort of doubtful permanency at Hartford; a strong, well-established palisaded block-house at Windsor; both of these engaged in trade with the Indians; and a small handful of planters - some twenty-five or thirty - in the meadows of Wethersfield - all in the midst of half friendly and hostile Indians."
"Within two months - by August 16, 1635 - a settlement was made by [Dorchester people] on the Connecticut. Their unfortunate selection of the lands adjoining the Plymouth block-house led to a lengthy dispute and considerable ill feeling between the two colonies. ... This disputed "Lord's Waste" is now the town of Windsor. ... While this dispute was in progress... a third claimant appeared. This was the Stiles party, which, sent from England by Sir Richard Saltonstall, one of the Connecticut patentees, had arrived in Boston, June 16, for the express purpose of settling in Connecticut. They were sent out from the Bay ten days later, and probably arrived sometime after the 6th of July. This party of servants numbered sixteen, and included three women, the first of their sex in the Connecticut valley."
"... Before the differences already mentioned had been permanently settled, and while the Dorchester emigrants were subduing the fields and forests of Windsor for habitation, in spite of the Plymouth land claims, word was returned to their townspeople left behind that the way was prepared. On the fifteenth of October there started from the Bay colony a body of sixty men, women, and children, by land, with their cows, horses, and swine. Their household furniture and winter provisions had been sent by water, together with probably a few emigrants to whom the overland journey would have proved too tedious. The majority of these people were from Dorchester, but accompanying them were others from Newtown and Watertown, who joined the townspeople on the ground they were cultivating."
"The period [1636] of unicameral government was the time of greatest emigration, "the special going out of the children of Israel." ... It is worthy of note that many of the Connecticut settlers continued to hold lands in the Bay colony for some time after their withdrawal to Connecticut. ... Every effort was made by the home government at the Bay to check this flow of emigration, or at least to turn its current into more adjacent channels; but the bent of the emigrant's spirit was toward Connecticut, and for the time being the colonial government was helpless to prevent it. ... The emigration grew less and less until 1638, and though large numbers came to Massachusetts that year, very few seem to have come to Connecticut. ... The Pequot war was not without its effect, but the Massachusetts men without doubt abused Connecticut. ... The report was spread that all the cows were dead, that Hooker was weary of his station, that the upland would bear no corn, the meadows nothing but weeds; that the people were almost starved in consequence. Such reports, spread abroad in the streets, at the inns, and even in England before embarkation, are a little astounding.
"As before intimated, by 1637 the tide of emigration had almost ceased. After-comers were not few, indeed, but the movements which gave birth to a new colony had practically reached an end."