As Caleb gets to know Bethia, the daughter of a Puritan pastor, he takes interest in the concept of the God that she believes in and in the ability to glean wisdom from a book.

Later, after Caleb's father dies of smallpox, he comes to live with the Mayfield family, thereby moving into a Puritan household and becoming further assimilated into the culture. Right up until his death from consumption a number of years later, Caleb retains a close relationship with Bethia, thereby remaining closely associated with the Puritan culture. By studying at the Indian School at Harvard for four years, Caleb and Joel gain further knowledge of a culture outside their own.

Ultimately, by coming into association with Bethia and leaving behind the lifestyle of the Wampanoag, Caleb becomes assimilated into Puritan culture.

Although Caleb retains part of his real name by using the combined name of “Caleb Cheeshahteaumau,” the fact of his entry into Harvard College in 1660 is a decisive step in leaving his own Wampanoage (Wopanaak) culture. All the colleges in what became the US were run by colonial powers and had a tiny handful of non-Euro-heritage students, who were in highly segregated conditions.

Long before starting college, however, Caleb began his assimilationist journey into the Puritan realm. Befriending Bethia can be considered one step, including his accepting the idea of her book as property. Brooks, however, presents their friendship as a two-way street which includes Bethia learning Caleb's language as well.

Literacy, through tutoring with an English-heritage colonist—Bethia’s father, Pastor Mayfield— was one important step. These lessons included catechization and renaming, consistent with the pastor’s goals of conversion/salvation. The staunchly Protestant Puritans further imposed cultural norms of hygiene and dress. Learning also included living in the teacher’s household in the Anglo town of Great Harbor. Another significant point comes when Caleb insists on speaking English only.

The literal crossing, when he was sent from Martha’s Vineyard to mainland Massachusetts to continue his study, is another significant step away from his culture.

One way in which Caleb assimilates is through his name change.  He takes the name "Caleb" as a nod to Puritan society.  This social setting would have seen his indigenous name as "idolatry" or something that breaks the covenant between human being and the Puritan divine.  Additionally, Caleb elects to study and further his study at Harvard.  This is representative of how Caleb embraces the Puritan ethic of formal study and movement away from his own Wampanoag roots.  Additionally, Brooks depicts Caleb as experiencing academic success. The fact that Caleb does not oppose the imposition of Puritan ways upon him and actually strives to do well in a more Puritan setting at Harvard than his own indigenous setting reflects his assimilation towards life in the Puritan way. While Caleb is aware of "the other" in terms of his own rootes, he is shown to embrace the assimilation of moving into Puritan social settings and adhering to their expectations of the good.  Caleb's most emphatic nod to Puritan assimilation is that he really shows little in way of opposition to Puritanical notions of the good.  It is evident that there is discrimination against the Native Americans and the desire to convert them from "idolatry" into Puritan notions of the good are both evident.  Caleb is not an agent of change in this regard. He does not stage mass rebellion.  Rather, he is shown to be affirm assimilation through his actions in the narrative.