Entrepreneurship can have transformative impacts that benefit rural areas and uplift underserved communities. In higher education, entrepreneurship instruction has grown over the last half century but is in its nascent stage in nonformal youth development settings. This chapter highlights the value of Extension youth entrepreneurship education programs that are contextualized, account for the audience’s unique needs and available resources, are designed with clear program goals to frame effective delivery and evaluation, and that build capacity for sustainable programmatic implementation. We further propose that Extension can draw from and capitalize on the current literature on entrepreneurship and entrepreneurship education for best practices in program development. Finally, we describe UpStarts, an entrepreneurship program that is intended to support positive socio-cognitive outcomes (e.g., entrepreneurial mindsets) and foster social connections among youth in rural communities. Implications focus on the role of Extension in translating research to effective practices to support youth entrepreneurship education in the communities.