Plymouth determined to wait no longer, and in October, 1633, sent a vessel, commanded by William Holmes, with workmen and the frame of a building for a trading-post. When they arrived in the river, they were surprised to find other Europeans in possession. The Dutch, aroused from their dream of security by the growth of the English settlement, made haste in the June previous to purchase from the Indians twenty acres where Hartford now stands, upon which they built a fort a short time after. When the vessel bearing the Plymouth traders reached this point in the river, the Dutch commander, John van Curler, commanded Holmes to stop and strike his flag. But Holmes, paying little attention to the threats of the Dutchman, continued his voyage and established a rival post ten miles above, at a place now known as Windsor.[38 ]

Meanwhile, the ship which Winthrop sent to Connecticut went onward to New Netherland, where the captain notified Governor Van Twiller, in Winthrop's name, that the English had a royal grant to the territory about the Connecticut River. It returned to Boston in October, 1633, and brought a reply from Van Twiller that the Dutch had also a claim under a grant from their States-General of Holland.[39 ] In December, 1633, Van Twiller heard of Holmes's trading-post and despatched an armed force of seventy men to expel the intruders. They appeared before the fort with colors flying, but finding that Holmes had received reinforcements, and that it would be impossible to dislodge him without bloodshed, they returned home without molesting him.[40 ]

The Plymouth settlers were destined to be dispossessed, not by the Dutch, but by their own countrymen. The people of Massachusetts were now fully aroused, and the news that came to Boston in the summer of 1634 that the small-pox had practically destroyed the Indians on the river increased "the hankering" after the coveted territory.[41 ] The people of Watertown, Dorchester, and Newtown (Cambridge) had long been restless under the Massachusetts authority, and were anxious for a change. Dorchester was the residence of Captain Israel Stoughton, and Watertown the residence of Richard Brown and John Oldham, all three of whom had been under the ban of the orthodox Puritan church. At Watertown also had sprung up the first decided opposition to the aristocratic claim of the court of assistants to lay taxes on the people. As for Newtown (now Cambridge), its inhabitants could not forget that, though selected in the first instance as the capital of the colony, it had afterwards been discarded for the town of Boston.

In all three towns there was a pressure for arable lands and more or less jealousy among the ministers. Some dissatisfaction also with the requirement in Massachusetts of church-membership for the suffrage may have been among the motives for seeking a new home. At the head of the movement was the Rev. Thomas Hooker, a graduate of Emmanuel College, Cambridge, who had lived in Holland, and while there had imbibed a greater share of liberality than was to be found among most of the clergy of Massachusetts. Cotton declared that democracy was "no fit government either for church or commonwealth," and the majority of the ministers agreed with him. Winthrop defended his view in a letter to Hooker on the ground that "the best part is always the least, and of that best part the wiser part is always the lesser." But Hooker replied that "in matters which concern the common good a general council, chosen by all, to transact business which concerns all, I conceive most suitable to rule and most safe for the relief of the whole."

Hooker arrived in the colony in September, 1633,[42 ] and in May, 1634, at the first annual general court after his arrival, his congregation at Newtown petitioned to be permitted to move to some other quarters within the bounds of Massachusetts.[43 ] The application was granted, and messengers were sent to Agawam and Merrimac to look for a suitable location.[44 ] After this, when the epidemic on the Connecticut became known, a petition to be permitted to move out of the Massachusetts jurisdiction was presented to the general court in September, 1634. This raised a serious debate, and though there can be little doubt that Winthrop and the other leaders in Massachusetts shrewdly cherished the idea of pre-empting in some way the trade of the Connecticut, against both the Plymouth people and the Dutch, an emigration such as was proposed appeared too much like a desertion. The fear of the appointment by the crown of a governor-general for New England was at its height, and so the application, though it met with favor from the majority of the deputies, was rejected by the court of assistants.[45 ]

The popularity of the measure, however, increased mightily, and there is a tradition that in the winter of 1634-1635 some persons from Watertown went to Connecticut and managed to survive the winter in a few huts erected at Pyquag, afterwards Wethersfield.[46 ] The next spring the Watertown and Dorchester people imitated the Newtown congregation in applying to the general court for permission to remove. They were more successful, and were given liberty to go to any place, even outside of Massachusetts, provided they continued under the Massachusetts authority.[47 ]

Then began a lively movement, and Jonathan Brewster, in a letter written from the Plymouth fort at Windsor in July, 1635, tells of the daily arrival by land and water of small parties of these adventurous settlers. Their presence around the fort caused Brewster much uneasiness, since some began to cast covetous eyes upon the very spot which the Plymouth government had bought from the Mohegans and held against the Dutch.

As their numbers grew their confidence increased; and finally the men of Dorchester, headed by Roger Ludlow, one of the richest men in Massachusetts, pretending that the land was theirs as the "Lord's waste," upon which "the providence of God" had cast them, intruded themselves into the actual midst of the Plymouth people. The emigrants from Plymouth protested, but were finally glad to accept a compromise, though, as Bradford remarks, "the unkindness was not soon forgotten." The Massachusetts settlers held on to fifteen-sixteenths of the land, while they magnanimously conceded to the Plymouth people one-sixteenth, in addition to their block-houses.[48 ]

The emigration in the summer of 1635 was preliminary to a much larger exodus in the fall. In October a company of about sixty men, women, and children, driving before them their cows, horses, and swine, set out by land and reached the Connecticut "after a tedious and difficult journey";[49 ] but the winter set in very early, and the vessels which were to bring their provisions by water not appearing, they were forced to leave their settlement for fear of famine. They were fortunate to find a ship frozen up in the river, which they freed from the ice and used to return to Boston. The other settlers who remained upon the river suffered very much, and were finally reduced to the necessity of eating acorns and ground-nuts, which they dug out of the snow. A great number of the cattle perished, and the Dorchester Company "lost near £2000 worth."[50 ]

These calamities were soon forgotten; and as soon as the first flowers of spring suggested the end of the dreary winter season, the Newtown people prepared to move. Selling their lands on the Charles River to the congregation of Rev. Thomas Shepard, the whole body, in June, 1636, emigrated through the green woods, musical with birds and bright with flowers, under the leadership of their two eminent ministers, Thomas Hooker and Samuel Stone.[51 ] Among the lay members of the community were Stephen Hart, Thomas Bull, and Richard Lord.[52 ] A little later the churches of Dorchester and Watertown completed their removal, while a settlement was made by emigrants from Roxbury under William Pynchon at Agawam, afterwards Springfield, just north of the boundary between Massachusetts and Connecticut.[53 ]