A combination of youth out-migration and lack of in-migration have led to an aging workforce and population decline in resource-dependent communities, while simultaneously declines in pulp and paper demand and biomass utilization have had negative impacts on the perceived future of the once-dominant forest products industry. These changes may increase uncertainty as to the availability and training of the next generation of workers and rural community residents. While many studies have explored the effects that these changes have on adult populations, little attention has been paid to how local labor markets and perceptions of future opportunities influence the next generation of workers, entrepreneurs, and community leaders. This research illuminates the relationships between employer educational needs, community characteristics, current student skills, and young people’s aspirations in traditionally forest-dependent communities through the delivery of surveys to middle and high school students, college students, and forestry employers in northern Maine and coastal Oregon. Possible education gaps between employers and current students were assessed in soft skills, knowledge skills, technical skills, and work culture domains. To further our understanding of rural youth educational and residential aspirations, the potential impact of the educational system, local economy, and community were investigated