We examine how aspects of community context (i.e., social and familial attachments, attachment to place, and economic environment) are linked to rural emerging adults’ educational and occupational experiences and aspirations. We use a year of qualitative interview data and 2 years of longitudinal survey data to explore how community context may shape two groups of rural emerging adults’ aspirations for those who remain in their rural home community posthigh school graduation and those who leave after high school to seek opportunities elsewhere. We found that the declining economic context of these rural communities shaped educational and occupational aspirations of both groups toward practically focused occupations. Interviewees struggled to balance their positive community attachments with the area’s lack of occupational opportunities. Our work uniquely underscores that analysis of community context may be a key to understanding emerging adults’ educational and occupational pathways and aspirations in economically strained rural environments.