Multiuse arts and crafts as well as recreational trails have been introduced to Central Appalachia as strategies to address community economic development. Over forty Kentucky communities have started down the pathway to become Kentucky Trail Town resulting in 16 certified trail communities. The Entrepreneurship for the Public Good Program at Berea College in community collaborative projects with city, county, state and national organizational and NGOs has pioneered experimental models over six years that has resulted in an interstate project integrating historic and heritage assets, leisure and cycling tourists and early stage new venture start up and business expansion. This paper analyzes the outcome of City of Berea Kentucky Trail Town leaders and community volunteers to expand trail routes, increased community asset mapping, and conduct customer discovery interviews with both cyclists and history preservation advocates, conversing with small business owners and merchants on ways to promote their goods and service, and assessment of the health impact of trail routes in Rural Appalachia. Early results of pilot studies are presented.