Municipal reform has accelerated since the 1980s, with municipalities learning to adjust to changes in responsibilities downloaded by senior governments. However, small municipalities struggle with outdated financial and jurisdictional structures as senior governments ask them to become more 'entrepreneurial' for a broader range of responsibilities. To date, little research has explored the influence of statutory settings that shape municipal powers, and hence, an understanding of the concept and associated processes pertaining to municipal entrepreneurialism. Drawing upon key informant interviews in four regions across Canada, this paper explores how small municipalities are generating revenue and other resources needed to address community and economic development priorities. Findings indicate that small municipalities are engaging in a variety of entrepreneurial activities, including municipal enterprises, social enterprises, and service contracts, while pursuing pro-active approaches to leverage place-based assets. These endeavours, however, are shaped by many dimensions of risk that underline the conceptualisation of municipal entrepreneurialism. [ABSTRACT FROM AUTHOR]