Variability in regulatory structure and climate can impact green infrastructure projects and policies in smaller communities (<50,000). To examine how these factors can constrain or catalyze green infrastructure projects, we facilitated the development of two green infrastructure demonstration and education projects in Coos Bay and LaGrande, two small communities in the state of Oregon, USA. Concurrent with the development of these projects, we conducted interviews with local community leaders and natural resource professionals in 12 other small communities to broaden our understanding of catalysts and constraints pertaining to implementation process. This research illustrates that implementing and sustaining green infrastructure projects in small communities can have an unique set of constraints. For example, both unwieldy regulations and a lack of regulations constrain green infrastructure implementation. We found that in small communities that fell under federal regulations, stakeholders felt constrained by the regulations, particularly given the limited capacity of staff, expertise, and funding to comply with these regulations. Conversely, communities that were not under regulatory edicts we able to take a more flexible approach. Catalysts that can help drive and sustain green infrastructure projects include close relationships with staff, landowners, and the public, and a dedicated source of funding.