In light of declining rural economies and dissipating rural populations, scholars, policy makers and program developers have increasingly looked to local business development and entrepreneurship as a means of revitalizing small communities across the United States. This study explores the perceptions of youth and business owners regarding the unique challenges and benefits or rural contexts for entrepreneurship, as well as perceptions regarding the potential role of youth in contributing to rural economies. Drawing from in-depth interviews and focus groups among local business owners and young rural residents, findings support earlier research regarding structural challenges that hamper rural business development (e.g., weak infrastructure) but also shed light on social challenges brought about by small and tightly bonded communities (e.g., openness to unfamiliar businesses). Notwithstanding these challenges, findings also suggest several perceived benefits of small communities such as local support for residents' enterprises and ease of communication with one's customer base. Finally, business owners expressed placing a high value on rural youth and their potential to make unique contributions to business development, nonetheless, found challenges around providing meaningful hands-on experiences for youth to learn about business operations.