Planner, conservationist, forester, and geographer Emile Benton MacKaye envisioned a revolutionary, extensive foot trail that would promote the interaction between communities throughout the United States' distinctive eastern region. His 1921 plan for the Appalachian Trail (A.T.) focused on balancing the basic requirements for life in and out of the urban context by developing an ‘indigenous’ environment and developmental mold (Bower 1962, 372). However, almost a century has passed, and MacKaye's approach to the planning process, organization, environmental development, and the rural economy remains hidden beneath the mountain forest canopy extending from Maine to Georgia. Four of the forty-nine designated communities in the A.T. CommunityTM program today were analyzed to determine if and which aspects of Benton MacKaye's original vision of regional planning were achieved 100 years later. On-the-ground observations were collected through informal interactions with A.T. CommunityTM Supporters, unaffiliated businesses and organizations, and locals while traveling to each of the four A.T. regions, defined by the A.T. Conservancy (ATC). It was essential to understand if the designations transformed trailside neighborhoods into outdoor recreational and social hubs and shifted community perspectives toward the Trail and the ATC. Although most people think of the A.T. purely in terms of the opportunities it provides for outdoor and wilderness experiences, it is also perceived as a critical focus for communities' economic growth and vitality. The research reveals that the program and its complimentary ‘Supporter’ system for local businesses are ineffective. The ATC branded these trail towns. Yet, no elements of MacKaye’s vision or community improvements have truly been recognized following A.T. CommunityTM designations within the last decade. Regardless of geographic, temporal, internal, and physical aspects, this outcome was consistent in all four case study communities (Monson-ME, Harpers Ferry-Bolivar-WV, Damascus-VA, and Hot Springs-NC).