The island-nation of Dominica, 790 km2 in area, is located approximately 1126.5 km Southeast of Florida, USA. In the mid-1990s, Dominica embarked on developing the 183.5 km Waitukubuli National Trail (WNT), the first and only national trail model in the Eastern Caribbean. The 14-segment WNT, officially opened in May 2013, passes through some of the island’s most diverse landscapes. WNT was designed to link as many rural communities as possible and promote ecotourism and community socioeconomic development. Rehabilitation work continues on the WNT and the rest of Dominica, following the devastation caused by Hurricane Maria of 2017. This article, based primarily on a limited questionnaire survey, selected interviews, and literature review, explored the research question ‘What were the challenges faced by a small-island nation in the development of a National Trail? Five specific research objectives focused on the conceptualization, implementation challenges, partnerships fostered, national and sub-regional significance, and future outlook of the Trail were considered. Questionnaire respondents identified the island’s topography and negotiations with private landowners as significant trail construction challenges. A 100% of survey respondents anticipate that reliable funding to support timely maintenance would likely be a critical future issue. Some respondents identified marketing, public engagement, and visitor safety as potential issues. Face-to-face interviews found strong support for the WNT. The interviewees were confident that Dominica would realize sustainable socioeconomic benefits from the Trail. The article concludes with lessons learned and proposes strategies and research themes to ensure the Trail’s sustainability