The 1869 will of wealthy businessman Thomas Thompson established a trust fund "for or towards the relief and support of poor seamstresses, needle-women and shop girls, who may be in the temporary need from want of employment, sickness, or misfortune, in the towns of Brattleboro, Vermont and Rhinebeck, Dutchess County, New York, the amount being equally divided between the two towns." Thompson's will also required that surplus funds be distributed to other charities in the same towns. Finally, the will declared that the Trust itself would not go into effect until the death of his wife, Elizabeth Rowell Thompson, who died in 1899.

In 1901 the Thomas Thompson Trust (TTT) began to carry out its duties, directed throughout the twentieth century by several Boston-based businessmen and a series of local agents. One businessman in particular, Richards M. Bradley, a native of Brattleboro, was the guiding force of TTT for its first four decades. The first local agent, Augusta Wells, administered the Trust for most of its first twenty years. Florence Hemenway Wells succeeded her adoptive mother, serving as the Trust's local agent from 1921 until the early-1960s. By then, most of the work of the Trust had been taken over by government agencies.

By 1901, when TTT was ready to begin dispensing funds to the "needlewomen" of Rhinebeck and Brattleboro, the very nature of women's work had changed drastically in the three decades since Thompson's will was first written. In Brattleboro, in particular, there had been significant demographic change. Instead of working from their homes or in small shops employing only a handful of people, an increasing number of the town's working women labored within one of several factories. Furthermore, a significant portion of these women were immigrants from the rural countryside or from other countries, especially Ireland. These demographic changes, unanticipated by Thompson in 1869, shaped the decision making of the lawyers appointed to organize TTT. The organizers were also influenced by Progressive era ideas, and since Thompson's will did not specify a plan for disbursement of funds, they were free to devise a plan within the context of those ideas.

Soon after the creation of the Trust was announced in the local papers, the working women of Rhinebeck and Brattleboro formed local committees in an effort to make the best use of the funds available to them. At the same time, the first trustees appointed to oversee TTT, Richards M. Bradley and Boston-based lawyer, Laurence Minot, had their own vision of just how, and to whom, the Trust should dispense its funds in Brattleboro and Rhinebeck. Guided initially by a traditional sense of noblesse oblige, Bradley, in particular, increasingly sought to shape TTT as a model of Progressive era reform, especially in Brattleboro. Thus, from the beginning, TTT sought to prevent illness among working women and their families through public health programs that stressed education in diet and infant care, and by promoting affordable health care. At the same time, small amounts of money were dispensed outright to women in need, sometimes in the form of a loan.

One of TTT's first major contributions to the town of Brattleboro was the funding of Brattleboro Memorial Hospital. The hospital, opened in 1904, provided hospital care at a reduced rate for those women covered by the Trust. In 1907, the Brattleboro Mutual Aid Association (BMAA) was created and funded by TTT as a way to oversee direct aid to the working women of Brattleboro. Under the aegis of the BMAA, a district (or public) nursing program to oversee education and treatment was established. The BMAA also oversaw a service providing attendant (or practical) nursing service for working women confined to their homes during a serious illness. For those women simply needing a rest, the BMAA ran a vacation house in Niantic, on the Connecticut shore, from 1910 to 1936. In 1917, responding in part to a nation-wide nursing shortage precipitated by World War I, the BMAA created an attendant nursing school while the hospital maintained a training school for graduate (today known as registered) nurses. In this way, TTT sought to address a potential crisis of care and at the same time provide the opportunity for Brattleboro working women to leave factory work for a more professional (and presumably more lucrative) career. The Influenza epidemic of 1918-19 further emphasized the need for trained health care professionals. The nursing schools remained an important function of TTT throughout the twentieth century.

In 1919, the Town of Brattleboro brought another lawsuit against TTT. The Board claimed that TTT continued to not meet the intent of Thompson's will because they were administering the dispensation of funds inadequately. The working women of Brattleboro, through their organization, the Society of Seamstresses, filed their own complaint but did not join the suit which dragged on for several months before a Massachusetts court ruled in favor of TTT in early-1921. Although technically the victor in the case, Richards M. Bradley was chastened by the legal ordeal and sought to expand the activities of TTT. The Trust increased outright aid and began an ambitious insurance program in the mid-1920s, open to all Brattleboro residents regardless of gender, occupation, or need. The Thompson Benefit Association for Nursing Service (1926) and the Thompson Benefit Association for Hospital Service (1927), each for a small yearly premium, provided coverage for home nursing care as well as the costs associated with a hospital stay. These programs, too, were administered by Florence Wells as TTT's local agent. They would eventually be replaced in the 1950s by commercial health insurance offered in the workplace by Vermont Blue Cross/Blue Shield.

The New Deal profoundly altered the work of the Trust as, for example, the Social Security Act became law. By the early 1960s, Florence Wells herself was a patient at Thompson House, TTT's nursing home in Brattleboro. Her care was funded both by the Trust and the Great Society program, Medicare. The Trust continues to exist in both Brattleboro and Rhinebeck and in 2001, celebrated its centennial in both communities.