Homelessness is a problem that plagues both urban and rural communities across the nation. The Upper Valley is not immune to this struggle. In fact, homelessness poses a particularly difficult problem in this region for a variety of reasons starting with the difficulties of collecting good data. Due to methods themselves and the differences in methodology in Vermont and New Hampshire, it is difficult to quantify Upper Valley homelessness accurately. Michael Redmond, Executive Director at the Upper Valley Haven, a White River Junction, VT nonprofit organization that seeks to alleviate rural poverty in a variety of ways, commissioned a report to understand better the correlates of homelessness in the Upper Valley. This report compiles existing data and analyses on the homeless and the resources available to them. The goal is to understand what problems are faced by homeless individuals and families in the Upper Valley, the causes of their situations, and what could potentially be improved. A historical lens is used to explore trends from the past (if existent), current key issues, and likely problems for the future. From there, solutions are investigated based on the continuation and expansion of current programs or the implementation of programs that have been used in other communities. This report looks at the problem of homelessness through three areas: (1) the local environment that dictates the locations, movability, and survivability of the homeless; (2) the health conditions and issues faced by the homeless and household/family structures; and (3) the human potential in the homeless population especially concerning employment and education opportunities. It also provides information on resources and programs available to impoverished and homeless people in the Upper Valley. Altogether, we seek to understand the homelessness problems in the region and place them in the context of time to provide options to the Upper Valley Haven on how to continue addressing the issue in the most efficacious manner.