The development circumstances of small population municipalities along The Great Trail vary widely and numerous expressions of precarious trail development were uncovered through a mix-method approach. This research introduces a novel approach to examining capacity, one which looks at the subjective development confidence of key-informant practitioners, which is used as a benchmark in analyzing qualitative data. Lower confidence-score municipalities express more development challenges associated to securing funding and improving collaboration with key-partnerships, but improving the quality of local Great Trail infrastructure is shared across confidence groups due to continued maintenance of trail spaces. Through temporal modelling, municipal participants express higher confidence levels related to previous and long-term development efforts, as compared to development circumstances in the short-term. Trail development was expressed to be largely the function of local municipal efforts and the TCT was the second most impactful supporter. Other examined partnerships express the importance of volunteers and a substantial degree of precariousness offered by governmental support.