Caleb's Crossing is a novel about Cheeshateaumeuck, who was the first Native American to graduate from Harvard University. Caleb meets a girl named Bethia in what is now Martha's Vineyard, who came from England to escape religious persecution. They give each other names, Cheeshateaumeuck calls her Stormy Eyes, and Bethia calls him Caleb (this is where we get the title "Caleb's Crossing"). Bethia eventually gets Caleb to convert to Christianity, and he lives in Bethia's house to study under her father. He is studying with another Indian student named Joel, and Bethia's brother Makepeace. While they are studying Bethia is denied the chance to do so too. During a sea voyage Bethia's father dies, so now they are left without a father and a teacher. Makepeace gets a tutor in Cambridge, both Joel and Caleb goes too. They strive at school and then Caleb and Joel move on to Harvard, where they both die around graduation time. Bethia marries Samuel Corlet and lives an easy domestic life; Makepeace abandons the scholar life, and finds happiness in being a husband and a father. There are a number of themes prevalent in this novel, especially the relationship of white people to the Indians. The white people try to take over the Indian land, give them small pox, and the relationship between the two populations results in a war.
The bad relationships between the white settlers and the Indians first start in chapter two, when Bethia's father explains what happened between their grandfather and governor John Winthrop. He tells them that even thought hat Winthrop was a powerful leader he used violence to keep his people obedient. He not only did this among his own people, but he did worse to the Pequot Indians. This is obviously not a good thing if you want to live on the same land and share the same recourses. While Bethia's father was talking about her grandfather he says "not all the sonquem's followers agreed with their chief some now say that he himself did not fully understand that meant to keep the land forever.