In Western Massachusetts, as in many regions of the United States, the municipalities with significant population size are significantly eclipsed in both number and area by the surrounding towns and villages. Struggling rural locations often face similar challenges to their urban counterparts: declining or failed industry, high levels of unemployment or under-employment, and lack access of quality housing across income classes. In addition to these obstacles, they also face additional difficulties of both physical and social isolation. While a great deal of recent effort has been placed in studying the architectural and planning interventions needed in struggling urban locations, rural areas have had little help from the field as a whole, often dismissed as unsustainable due to their lack of density. The focus on only the city fails to consider a larger picture of cities, towns, and rural communities, as an interconnected system. If those “unsustainable” rural communities were to be vacated, cities would rapidly discover significant problems in the realms of agricultural production, water supply maintenance, and a host of other benefits that exist in the symbiotic relationship between cities and the rural areas around them. Working towards a sustainable future requires changes to be made across the board of human habitation, and rural communities play a significant role in that goal. Rather than considering both scenarios in measure, focus remains tilted to the urban context, leaving rural practitioners and planners with few models for moving forward in socially and ecologically sustainable ways. This thesis attempts to rectify that absence. Another facet of this thesis is an attempt to address not only ideas of environmental sustainability, but the social equity, economic vitality, and supportive social systems that are required to meet those goals. Architecture is prone to disregarding the effects the built environment has on the community, but the heritage and culture of a place are always impacted by the construction of a new building, the renovation of an existing community landmark, or the development of new infrastructural systems. These cultural changes can be positive or damaging, depending on how attuned the designer is to current need, and to the involvement and agency of the community being affected. I have chosen to focus this thesis within my home region of Hampshire County. Ware, Massachusetts, located on the south end of the Quabbin Reservoir, is the county’s eastern-most town. Specific obstacles for a thriving rural community include lack of transportation and local job options, a struggling downtown with little successful social space, and a lack of quality affordable housing. The goal of this thesis is to propose an intervention that begins a dialogue with some of these challenges, looking at new options for connecting home, work and community as the beginning for a developing framework that is able to bring Ware into a more holistically sustainable future.