When Canada celebrated its 125th anniversary in 1992, an initiative was launched to have a Trans Canada Trail (TCT) by 2017—Canada's 150th anniversary, to pass through thousands of municipalities and communities from the Atlantic to the Pacific and, further, the Arctic coast. With a total length of over 27,000 km at present, the Trans Canada Trail has become the world's longest trail, which allows millions of users to be actively engaged in a variety of outdoor activities. The TCT brings Canadian citizens closer to nature while engendering a host of recreation and learning opportunities as well as health benefits. This study describes the evolution and milestones of the TCT initiative. A conceptual framework that embodies a Nature Continuum typology is proposed for exploring the relationships among the trail activities, trail types and the environment. The results lend support to certain elements of the Nature Continuum typology. A number of gaps of the TCT are identified, and necessary measures for addressing the gaps are discussed. Uniting Canadians physically and symbolically, the TCT is, nevertheless, a work in progress. An array of hurdles need to be surmounted down the road for the Trans Canada Trail to fulfill its mantle of aiding Canadians in their journey of active living. The Trans Canada Trail enables Canadians to stay active and close to nature. The study shows that the ‘Nature Continuum’ typology is a promising tool for managers to examine relationships between human activities and the environment along the Urban-Wilderness Spectrum. Managers of national trails should establish a national code of ethics including strategies to deal with trail users, to respect all signage and property, to avoid environmental damage, to inform trail users, to leave wildlife and plants alone and to stay on the trail. A national code of ethics will contribute to the desired behavioral change over time.