Kanawalohale was a village located in the present-day town of Vernon in central New York state. In the 18th century, it was an Oneida village located about 60 miles west of the Mohawk village Canajoharie. Because the village’s name was similar to the Mohawk village of Canajoharie, many sources conflate the two. Founded in the mid-18th century, Kanawalohale was made up of a cluster of about 40 homes along the Oneida Creek, south of Oneida Lake. The name means head on a post in reference to an enemy soldier's skull displayed in the village. In 1765, David Fowler established an Indian school in Kanawalohale, where Wheelock’s son, Ralph, worked. Between the years of 1765 and 1767, Kanawalohale hosted many of Wheelock's missionaries including Samuel Kirkland, Joseph Johnson, David Avery, and Aaron Kinne. The Indians of Kanawalohale used their relationship with missionaries such as Kirkland to gain prestige over the formerly central Oneida village, Old Oneida. Kirkland often wrote in his journal about the dialogues he had with the Indians at Kanawalohale, who refused to receive his teachings silently. The Christian Indian population grew throughout the 1760s with at least 200 Indians attending church in the village. In 1780, Joseph Brant, a Mohawk allied with the British, led a war party against the revolting colonists, with whom the Oneidas had allied, that destroyed the Oneida village of Kanawalohale. This area is known today as Oneida Castle.

Connecticut is a state in southern New England that borders Massachusetts to the north and the Long Island Sound to the south. Its name is derived from the Algonquian "Quonehtacut," meaning "long river," referring to the Connecticut, which runs from the border with Canada into the Long Island Sound. The area was originally inhabited by Algonquian-speaking Pequots, Mohegans, and Quinnipiacs. European settlers took advantage of tribal divisions to establish dominance in the region. Dutch explorer Adrian Block sailed up the Connecticut River in 1614, establishing an active Dutch trading post at what is now Hartford. English claims to Connecticut began in 1630, but settlement truly began when Thomas Hooker, a Congregationalist minister now known as "The Father of Connecticut," left Boston to found Hartford in 1636. Hartford became the center of the Colony of Connecticut, which did not receive its charter until 1662 when Governor John Winthrop, Jr. secured it from Charles II. In 1665, the Colony of New Haven, established in 1638 by the Puritan minister John Davenport, joined the Colony of Connecticut under this charter. Early settler relations with local Indians were tense, and encouraged the New England colonies of Massachusetts Bay, Plymouth, Connecticut, and New Haven to unify as the "United Colonies" or "New England Confederation" and fight together, with Indian allies, in the Pequot War and again in King Philip's (Metacom's) War. These wars helped establish a specifically Connecticut and specifically American identity; the latter drove the colony to join the rebellion against Britain in 1776. Occom, born into a Mohegan household in Connecticut, was closely associated with the Colony and retained strong ties to the region throughout his life. He converted to Christianity in 1743 when the Great Awakening spread through Connecticut, and inspired Wheelock's Indian Charity School, which was founded in Lebanon, CT in 1754. He also became involved in the Mason Land Case, a long-standing dispute over the ownership of reserve Mohegan lands in Connecticut. Wheelock also had strong ties to Connecticut, moving his Indian Charity School only when the colony would not grant it a charter.

David Avery was one of Wheelock's charity scholars and had a long career as a Congregationalist minister. He studied at Moor's and Yale, where he was David McClure's classmate, and received his Masters from Dartmouth in 1773. Avery went on several missions to Indian tribes before his health forced him to retire. His first mission, before his final year at Yale, was to Kanawalohale as a schoolteacher in the summer of 1768. While there, he attended the 1768 Treaty of Fort Stanwix as Wheelock's representative. After graduating, he served on Long Island around Smithtown. He was ordained August 29, 1771, at Dartmouth. Wheelock then sent him to the Oneidas for eleven months (September 1771 to August 1772), primarily to find out why the Oneidas had withdrawn their children from Wheelock's school. However, Avery's health was failing, and at some point between August 1772 and March 1773, he withdrew from Indian missionary service. In response, Wheelock charged him part of his tuition. Avery lived an exciting life after he left Wheelock's service. The Sabbath after the battle of Lexington (April 19 1775), he bade his Gageborough congregation farewell, mustered twenty men, and led them to Boston where he preached to the entire army. He enlisted as a chaplain, although he also fought in battle and served as a medic. He left the army in February 1780, and spent the rest of his life in a variety of pulpits, with a stint under the Massachusetts Domestic Missionary Society.

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.

Aaron Kinne was a Congregationalist minister and scholar who, like Titus Smith and Theophilus Chamberlain, worked as a missionary for Wheelock after graduating from Yale. After his 1765 graduation, he taught and studied at Moor's for a year before making two trips as a missionary in 1766: one to Maine to report on the local Indian tribes, and one to the Oneidas, the latter being cut short by poor health. He returned in the summer of 1768 to substitute for Samuel Kirkland. Kinne was ordained in 1770 and became the minister of the Congregationalist church at Groton, Connecticut, where he served until he was dismissed in 1798. He also became a prolific scholar, and during the Revolution, served as chaplain to American troops, including those massacred at the Battle of Fort Griswold. After dismissal from Groton, Kinne lived in a variety of locations in New England and was sporadically employed as a missionary. He died in Ohio while visiting one of daughters.