Mohegan is a village in southeastern Connecticut at the site of the present-day town of Montville, and is the location of the Mohegan Indian Reservation. The village gets its name from the Mohegan Tribe, or wolf people, who split from the Pequots in the early 17th century under the leadership of the sachem Uncas. In the 1720s, the Mohegans requested the colony of Connecticut provide them with an English educator. An English minister and schoolteacher named John Mason (no relation to Captain John Mason) moved to Mohegan in order to provide English-styled education to the Mohegans, convinced his sponsors, the New England Company, to build a schoolhouse at Mohegan, which eventually served as a boarding school for other Native American children from the surrounding area. During the 17th century, the Mohegan Tribe became embroiled in a complicated controversy over control of Mohegan land — known as the Mason Land Case or, more specifically, Mohegan Indians v. Connecticut — that included the village of Mohegan. The Tribe claimed that it never authorized a transfer of their lands, held in trust by the Mason family, to the colonial government. In 1662, the colony of Connecticut was incorporated by a royal charter, which included the disputed tribal land. The land controversy was revived in 1704 when descendants of John Mason, the original trustee, petitioned the Crown on behalf of the Mohegans, but the suit was finally decided against the Tribe in 1773. Born in Mohegan, Occom became involved in the Mason Land Case and vehemently argued for the rights of the Mohegan Indians to maintain their land, opposing Eleazar Wheelock and other ministers in the area. Although Occom left Mohegan for a 12-year mission with the Montauk Indians of Long Island, he returned at the end of 1763 with his large family to build a house in Mohegan, establishing it as his base of operations. Even after the creation of the Brothertown settlement in Oneida country, for which he served as minister, Occom continued to commute back and forth from Mohegan; he didn't sell his house in Mohegan and move his family to Brothertown until 1789. Many members of his family remained in Mohegan, including his sister Lucy Tantaquidgeon, who lived there until her death at 99 in 1830.

Lebanon Plains is a difficult term and place to definitively locate. According to the Lebanon Historical Society, there is a tradition that associates Lebanon Plains with the historical Lyman farm in Lebanon, a town in central Connecticut. Alternatively, the Historical Society suggests that Lebanon Plains may refer to the Lebanon green, an open expanse of land within the town of Lebanon.

Old Saybrook is a town located in southeastern Connecticut on the west bank of the Connecticut River, where it meets the Long Island Sound. The land that would become Old Saybrook was the territory of the Niantic Indians until the late 16th century when they were conquered by the Pequots. The first Europeans to settle in the area were Dutch, but by 1623 the colony failed due to harsh conditions. In 1635, English Puritans led by John Winthrop Jr. established a colony called Saybrook Plantation, hoping to deter the return of the Dutch. During the Pequot War of 1636, the powerful Pequot tribe conducted a siege of Saybrook Fort for eight months, but their population was ultimately decimated by the effort. Yale University, originally called Collegiate School of Connecticut, was founded in Old Saybrook in 1700 and then moved to New Haven in 1718. Because of its location, Old Saybrook was a convenient stopping point for Occom on his trips between Mohegan and Montauk, on Long Island, and was a point of embarkation for travel to other coastal cities by water. At least one Native American in Old Saybrook, the son of Josiah Wolcott, wanted to attend Wheelock’s school. Old Saybrook is one of the oldest towns in the state and was incorporated in 1854.

Virginia is a state located on the eastern seaboard in the mid-Atlantic United States. This area was home to several powerful chiefdoms including thirty-two Algonquian-speaking tribes that made up the Powhatan Empire and other nations including the Meherrins, Nottoways, Monacans, Manahoacs, Nahyssans, Occaneechis, Saponis, Tutelo Saponis, and Cherokees. When the English arrived in the late 1580s, they named the region after their virgin queen, Elizabeth I, and in 1607 established the first permanent English colony in the Americas. The Powhatans grew tobacco, and an English colonist, John Rolfe, introduced a new strand from the West Indies, which became a lucrative cash crop of Virginia. Rolfe’s wife, Pocahontas (born Matoaka), daughter of Chief Powhantan, was baptized and taken to London as an example of the possibilities for converted Indians. In the 1700s, the white population in Virginia increased as a result of the influx of German and Scottish-Irish immigrants. Africans were brought to Virginia to work in the tobacco fields, and in 1661, Virginia codified laws that condoned and regulated slavery. By 1776, forty percent of the new state’s population were Virginians of African origin or descent. Wheelock's letters from the 1750s contain several suggestions that his trained missionaries, including Occom, should be sent on missions to Virginia to teach Indians in that colony. In 1758, Samuel Davies of Virginia recruited Occom for a mission to the Cherokee Nation in Virginia and suggested that his ordination happen immediately in preparation (Occom was ordained in 1759 but by Presbyterians on Long Island), although this mission never happened.

Hezekiah Calvin was one of Eleazar Wheelock's first Native American students. Like Wheelock’s other early Delaware students, he was sent by the minister John Brainerd. Calvin was certified as a schoolteacher on March 12, 1765, and was sent to the Mohawks at Fort Hunter in June 1765. The Mohawks threw him out at the end of September 1766, and he returned to Moor's. Samuel Johnson, an Anglo-American Yale student who replaced Calvin at Fort Hunter, reported that the residents unanimously accused Calvin of being abusive and rude. Calvin, in turn, maintained that the Fort Hunter Mohawks had mistreated him. Calvin’s second stint at Moor’s did not go well. He wrote several confessions for drunkenness and bad behavior, and frequently spoke ill of Wheelock. He left the school in the spring of 1768, and took up residence with the Secutor family (Narragansett) at Charlestown, Rhode Island. Calvin left the Narragansetts sometime late in 1768, presumably after the dissolution of his relationship with Mary Secutor. Wheelock heard reports early in 1769 that Calvin had been imprisoned at Little Ease, NJ, for forging a pass for a Black man (Calvin does not appear in the county records, so either he was never indicted or Wheelock had his information wrong). By 1777, Calvin was in a position of prominence at Brotherton, NJ (a town of Christian Delawares founded under John Brainerd’s ministry). At some point after 1788, Calvin moved west with the Delawares: he may have moved directly to join the Delawares in Ohio territory, or he may have relocated to Stockbridge in 1802 and then moved west.

Eleazar Wheelock was a New Light Congregationalist minister who founded Dartmouth College. He was born into a very typical Congregationalist family, and began studying at Yale in 1729, where he fell in with the emerging New Light clique. The evangelical network that he built in college propelled him to fame as an itinerant minister during the First Great Awakening and gave him many of the contacts that he later drew on to support his charity school for Native Americans. Wheelock’s time as an itinerant minister indirectly brought about his charity school. When the Colony of Connecticut retroactively punished itinerant preaching in 1743, Wheelock was among those who lost his salary. Thus, in 1743, he began operating a grammar school to support himself. He was joined that December by Samson Occom, a Mohegan Indian, who sought out an education in hopes of becoming a teacher among his people. Occom’s academic success inspired Wheelock to train Native Americans as missionaries. To that end, he opened Moor’s Indian Charity School in 1754 (where he continued to train Anglo-American students who paid their own way as well as students who functionally indentured themselves to Wheelock as missionaries in exchange for an education). Between 1754 and 1769, when he relocated to New Hampshire, Wheelock trained approximately 60 male and female Native American students from nearby Algonquian tribes and from the Haudenosaunee (Iroquois) of central New York. At the same time, he navigated the complicated politics of missionary societies by setting up his own board of the Society in Scotland for Propagating Christian Knowledge, although he continued to feud with the Boston Board of the SSPCK and the London Commissioners in Boston (more colloquially called the New England Company). By the late 1760s, Wheelock had become disillusioned with the idea of Native American education. He was increasingly convinced that educating Native Americans was futile (several of his students had failed to conform to his confusing and contradictory standards), and, in late 1768, he lost his connection to the Haudenosaunee. With his inclination and ability to sponsor Native American missionaries largely depleted, Wheelock sought instead to fulfill his ultimate ambition of obtaining a charter and opening a college, which he did in 1769. To fund this new enterprise, Wheelock drew on the £12,000 that Samson Occom had raised for Moor’s Indian Charity School during a two-and-a-half year tour of Great Britain (1765 to 1768). Much of this money went towards clearing land and erecting buildings in New Hampshire for the Charity School’s relocation — infrastructure that also happened to benefit Dartmouth. Many of Wheelock’s contemporaries were outraged by what they saw as misuse of the money, as it was clear that Dartmouth College was not intended for Indians and that Moor’s had become a side project. Although Wheelock tried to maintain at least some commitment to Native American education by recruiting students from Canadian communities, the move did a great deal of damage to his public image. The last decade of Wheelock’s life was not easy. In addition to the problems of trying to set up a college far away from any Anglo-American urban center, Wheelock experienced the loss of relationships with two of his most famous and successful students, Samson Occom and Samuel Kirkland (an Anglo-American protégé). He also went into debt for Dartmouth College, especially after the fund raised in Britain was exhausted.