The desire to move up the social and economic ladder is a fundamental part of the American dream. However, for more than a half-century, millions of Americans have acted as if moving out to the suburbs is the same as moving up in life. Rather than stopping to think about how to make communities a better place to live, many have rushed headlong into the countryside, affecting the population stability of cities. In our haste to move up and out, we too often took our natural resources for granted. We pay little attention to what was happening to agricultural communities as development compromised forests, wildlife and farmlands.Gradually we are beginning to realize that our growth patterns are destroying our cherished landscapes. On top of its impact on farm and forest land, low-density, sprawling growth has destroyed the beauty of our communities, and forced our citizens to pay higher and higher taxes to meet the demand for sprawl-supporting infrastructure.Finally, we are beginning to realize that we need to rethink the way we grow. The need for features that could provide livable communities emerged out of this realization. Trails are one such feature that could improve livability, as they offer an innovative means of addressing sprawl, revitalizing urban areas, binding the communities, strengthening the economy and communities, and reusing degraded lands.Trails were traditionally developed as transportation corridors that connected various places. With the increasing number of people seeking outdoor recreation, the use of trails has gradually changed from transportation to recreation. And with trails contributing to the community and economic development, they are also considered a feature that contributes to a community's economy. Having multiple usages, trails have been among the prime choices of a planner working for the betterment of communities.This is a multi-faceted research project that studies recreational trails and their influence on community development. Research is done on trails, their utility, and the advantages and disadvantages of such a system on a community. Successful trails stories are researched, analyzed and discussed.This paper also uses a Geographic Information System, (GIS) as a research tool, to help refine, justify and enhance a proposed trail system in the city of Shelbyville, Indiana. It is used to analyze the proximity of distances from the proposed trail system to some of the city's resources. More importantly, this study develops GIS modeling methodologies for analysis of a recreational trail system.Census data, demographics, median house value, and median household income, are used to compare and assess neighborhood conditions. This analysis is used to assess the potential use of the proposed Shelbyville trail and to help refine the proposed location. This same data is also used as an indicator to help predict the economic growth along the proposed Shelbyville trail system.A GIS can be a powerful tool to help in trail placement and for identifying and assessing community based economic opportunities of a trail. The conclusions reached in this paper will show that a GIS can be utilized as a tool to help stimulate and build on the economy of a city and the community as a whole.