[2] Reverend John Sergeant described his efforts in this way: "Mr. Woodbridge ... has a very numerous school and a tedious task of it; lives a very lonesome life; is indeed indefatigable in his business; and no body deserves more of the publick than he.

He was instrumental in the purchase of large tracts of land in western New England from the Native Americans, such as modern-day Lenox and Alford, Massachusetts, by parlaying this reputation and experience.

[6] John Sergeant had arranged to return to Yale to complete his duties as a tutor, so the ministers associated with the mission sought Timothy out as an ideal candidate, due to his education, family history, and possibly, knowledge of their language.

[9] On January 19, 1735, a council with Mahican leadership was held, and they voiced their desire that Timothy would remain with them, and that John Sergeant would return to live among them.

[10] However, not all of the Mahicans agreed that they should submit to the English lifestyle, and rumors circulated that there was resentment about Chief Konkapot and Umpachenee being given military commissions by Governor Jonathan Belcher, as well as the mission in general.

When Sergeant returned to Yale again, he wrote Dr. Colman, one of the Commissioners of Indian Affairs at Boston, and requested that Timothy would be compensated so that he might continue there, being that there was enough work for two missionaries.

During the winter of 1736, Sergeant and Woodbridge decided to accompany the Mahicans on their maple syrup harvest, so that their education could continue, uninterrupted.

On March 25, the General Court granted a township on the Housatonic River, which would become Stockbridge, to the Mahicans, so that they could all live in one place, facilitating their education.

[15] The Woodbridges had built a house, the first permanent residence in the township, by January 1737, and John Sergeant lodged with them at this time, to live among his congregation.

[16] In 1737, Timothy and Abigail served as witnesses to a land deal between Colonel John Stoddard and the Native Americans, comprising the modern town of Pittsfield.

[18] Timothy was the senior deacon of the church, and identified as a New Light regarding the contemporary Great Awakening (he would later help recruit Jonathan Edwards, and become his greatest ally in Stockbridge).

The Mahicans had many complaints, including that Timothy had illegally purchased a tract of land without the consent of the entire tribe, so a committee was sent to investigate.

They requested that a new teacher be sent, and Gideon Hawley arrived in February 1752 to teach the Mohawks and Oneidas (the resident Mahicans were still taught at Woodbridge's school).

[31] In April, Timothy and other supporters of Edwards met to encourage the few remaining students' families that they should remove their children from Kellogg's classes.

In addition to being elected as a representative, Timothy, by then known to the Native Americans as Solohkuwauneh, was made a Justice of the Peace in 1752, at the recommendation of Edwards.

There was a near uprising in town when a man named Wampaumcorse, a Schaghticoke volunteer detective, was killed by white men after he approached them, regarding horses he believed they had stolen.

This, too, was delayed, and Edwards wrote to expedite the payment, and it was finally made, which mostly quelled the potential uprising, but left some harsh feelings.

[39] In an effort to strengthen their relationship with the Iroquois Nation, the British organized the Albany Congress from June 19 to July 11, which Timothy attended, working behind the scenes to secure the Susquehanna purchase for Connecticut.

[40] The British had an ulterior motive for much of their interaction with the Iroquois nation, that of trying to win their affiliation against France, their frequent adversary in the quest to control the North American continent.

In October, Timothy Woodbridge met with some of the Canadian chiefs, to try to determine the reason for their unprovoked attacks, when the two parent nations were at peace (albeit very tenuously).

[41] At about the same time, Jonathan Edwards fell ill, and Dwight redoubled his efforts to regain control of the boarding school (and the funding that came with it).

In September, he was witness (as Justice of the Peace) to a deed of purchase of over 20,000 acres, including the modern town of Austerlitz, New York, from the Stockbridges.

[44] In October 1757, Timothy wrote to Thomas Pownall, requesting legislation restricting the sale of alcohol to the Native Americans.

[49] In January 1762, Timothy was the moderator for another meeting of the Susquehanna Company in Hartford, Connecticut, and was voted a member of the committee to prepare their case for King George III to confirm their purchase.

[50] In April, he wrote a letter to Governor Francis Bernard requesting help in apprehending the murderer of a Stockbridge man named Cheneaquun in Albany.

In November 1762, the Susquehanna Company voted him to be a part of a committee to meet with the Native American chiefs at Albany to discuss the purchase they had made, which was still disputed.

[54] In April, Timothy was elected president of a committee to lay out eight townships within the Susquehanna purchase, and to determine the method of settling these eight, as well as two other towns.

On this subject, Timothy lobbied the government during the winter of 1763-1764 and wrote to Andrew Oliver in November 1764, asking that they be allowed the same rights to sell their lands as the English.

[56] The same year, Timothy became involved with a grievance of the Wappinger tribe, regarding land claims in New York, and wrote to William Johnson on their behalf.

[63] In June, the Stockbridges petitioned that Timothy be allowed to sell as much as their land as was required, being that their tribe was greatly in debt, and some members imprisoned on those grounds.