In 1674, the Massachusetts missionary and magistrate Daniel Gookin traveled through the inland Nipmuc ("freshwater") country, visiting longstanding communities that he and his fellow settlers had recently designated "Praying Towns." Massachusetts colony sought to contain indigenous Massachusett and Nipmuc communities within bounded villages, led by Native converts under colonial jurisdiction. Gookin went on a "tour" in order to assess the progress of this political and religious goal and to survey "the numbers, names and situations of the praying Indian towns" for the colony and its benefactors in England; he found a diverse array of responses and adaptations. His account was published as Historical Collections of the Indians in New England over a century later, in 1792.
Among the primary places he described were Natick, the first Nipmuc town bounded and designated as a "Praying Indian Town," Hassanamesit (Grafton), "a place of small stones," the town on the Nipmuc (Blackstone) River where James Printer and his family lived. As Gookin noted, James's family formed the pillars of the town, which was well situated with fertile fields of "corn," fruit orchards, and "well tempered and watered meadows." James's brother Annaweekin was a leader, or "ruler" in the missionaries' terms, described by Gookin as "a sober and discreet man," while his father Naoas was a "deacon" and his brother Joseph Tukuppawillin was the teacher. Although Gookin acknowledged James's mother and his brothers' wives as among those pillars, neither he nor John Eliot acknowledged the women by name. The Nipmuc towns, although autonomous, were connected by bonds of kinship and trails of diplomacy. James and his brother Job Kattenanit worked as teachers in the neighboring towns of Waeuntuk and Okkanamesit. Both James and Job had been trained at the preparatory schools associated with the Harvard Indian College , which Gookin also described in his account.
Although Gookin tried to paint a positive portrait of his missionary endeavors, he acknowledged that some Indigenous leaders questioned or opposed the project as a whole. On his 1674 journey, a Mohegan ambassador challenged Gookin at Webquasset, a Nipmuc town southwest of Hassanamesit, relaying the message that the influential Mohegan sachem Uncas was “not well pleased that the English should pass over Mohegon River, to call his Indians to pray to God.” In describing "his Indians," Uncas was not merely asserting authority, but kinship. Such possessive pronouns in Algonquian languages (like Mohegan and Nipmuc) were markers of relationality. Uncas's family had long had kinship and marriage ties with Nipmuc people, particularly those closest to Mohegan. Given Webquasset's geographic location, the missionary’s arrival signaled to Uncas colonial encroachment from Boston toward his territory, and that of his kin.
While Mohegan leaders asserted jurisdiction in their territory and through their relationships of kinship and alliance with the people at Webquasset, Gookin asserted colonial bounds, claiming the right to preach conversion because Webquasset “lieth...within the Massachusetts town line.” He said that “Wabquisset was within the jurisdiction of Massachusetts and that the government of that people did belong to them.” Webquasset was geographically close to Mohegan and tied politically to Uncas, but “about seventy-two miles” from Boston. Although Gookin emphasized the colonial boundary between Massachusetts and Connecticut, a line that was not yet fixed, Uncas asserted continuing Native space, foregrounding the waterways, and creating a different boundary, between Mohegan and Massachusetts jurisdiction at the long waterway (Mohegan/Quinebaug) that connected Nipmuc towns to Mohegan.
At Webquasset, Gookin was hosted by a female leader, the sachem’s wife, since the "sagamore," whom he said was “inclined to religion,” was away. They gathered in a Council House that was “sixty feet in length and twenty feet in width,” surrounded by the newly gathered harvest of corn. In the Council House, Gookin spoke with the local teacher, a Hassanamesit man named Sampson Petavit, who like James Printer, came from a family of converts and had been schooled in Puritan teachings and English writing. An “active and ingenious person,” according to Gookin, Sampson often “stood in the gap against the pride and insolency” of those “wicked…sagamores” who opposed the missions. Clearly, Gookin was speaking of Uncas, but he may have also included the Narragansett saunkskwa Quaiapin, who challenged the missionaries' inroads with the Nipmucs at Quantisset, and Shoshanim or Sagamore Sam of Nashaway, whose leadership had been opposed by the missionaries.
The Massachusetts missionaries simultaneously asserted a global jurisdiction and pretended they were not interfering in “civil” or local political matters. In response to Uncas’s messenger, John Eliot asserted that “it was his work to call upon men everywhere…to embrace the gospel,“ but “he did not meddle with civil right or jurisdiction.” This claim must have seemed suspect, however, given that, as all of the “sagamores” could observe, the missionaries sought to establish governance in the “praying towns” by convert rulers that they approved, who would enforce colonial laws, including “obedience to the Gospel of Christ” and the “kingdom of heaven,” as well as the suppression of “idolatry” and other sins “among them,” that is, the practice of indigenous spiritual and cultural traditions. As female leaders like Weetamoo and Quaiapin could see, this included the suppression of women and the conversion of the fields, with men encouraged to take up the plow and animal husbandry, and women encouraged to leave the communal mounds and take up domestic arts like spinning. Moreover, women were to follow the rule of their convert husbands and town rulers. Thus, Uncas sought not merely to secure “tribute,” as Gookin suggested, but to protect the people of Webquasset and Mohegan from the impositions of Christian colonial rule. Meanwhile, men like James Printer had to wrestle with balancing the protection of their towns, as the “praying” designation preserved the bounds of their lands under colonial law, and the cultural transformations that missionaries sought to impose in return for their protection.