Results indicated a number of recurring themes in the young men’s accounts of their pathways to offending in their rural communities: boredom, visibility, suspicion of the community upon reentry, reputation, unable to return to own community after prison release, and early upheaval. Perhaps the most persistent story emerging from these interviews was the importance of community attitudes in pathways into offending as well as in their desistance from crime after prison release. The young men discussed the problems presented by high visibility within small communities and the ease at which bad reputations were earned and the difficulty of shaking them. The isolation of the rural environment coupled with a lack of activities appropriate for young people led to juvenile criminality as a way of seeking relief from boredom. Complicating matters for these young men was a severe lack of support services in their communities following their release from prison. The findings suggest the need to develop services to support the needs of young people in rural communities; services ranging from social and leisure activities to job training and crime control programs. Participants were 22 male prisoners aged 17 to 21 years who had been living in rural parts in England prior to their sentencing and who were recruited for the study through the induction, resettlement, and education program offered in their prison. Interviews were conducted between August and October of 2004 and focused on social networks and friendship groups, recreation and leisure, patterns of offending, community characteristics and involvement, and future aspirations. Interviews were transcribed and subjected to a thematic analysis in which common content categories as well as specific themes and subthemes were identified. Seven case studies are presented to illustrate the experiences of the young men. Notes, references