Solutions to sustainability transitions tend to be applicable for specific regions but not the whole of society. Limitations on what may be sustained also exist, and preferences will vary among people in different places. Because of these differences, there is a need for better understanding of the perceptions and experiences of local community members and the challenges they face in the transition toward sustainability to promote realistic and effective decision-making. As a region with significant natural resource protections, the Greater Yellowstone Ecosystem has been known to researchers for decades as an ideal location to study human-environment interactions. The objective of this study was to determine the challenges to sustainable community development and natural resource management identified by residents of communities surrounding Yellowstone and Grand Teton National Parks. Thirty-two key informant interviews were conducted with decision-makers, with a focus on the communities of Red Lodge and West Yellowstone, Montana, and Jackson, Wyoming. Findings suggest that primary challenges include the seasonality of the tourist industry, disparities between agricultural and tourism-dependent priorities, and the implementation of stated sustainability goals. Challenges differ based on communities’ socio-economic conditions, dependence on tourism and recreation-based industries, and the influence of local and extra-local institutions.