The transition to middle school is considered to be a heightened period for involvement in bullying because the lack of a defined dominance hierarchy is thought to promote jockeying for social positions among students. Accordingly, this study examined bullying in peer ecologies at the beginning of the middle grade years in rural schools that did and did not have a transition to middle school. Thirty-six schools (20 with transitions, 16 without transitions) participated in this research with a sample of 1,800 participants (52% female) who were in sixth grade during the second year of data collection. Overall, 67% were White, 19% African American, 7% Latino, 2% Native American, and 5% other (multi-racial, Asian, unknown). Compared to schools without a transition, schools with a transition had fewer bullies following the move from fifth to sixth grade and the social dynamics in schools with a transition appeared to be less supportive of bullying. Further, students in schools with a transition reported being bullied less frequently in sixth grade and they perceived the sixth grade peer ecology as being more protective against bullying than did students in schools without a transition. In addition, proportionally more youth had controversial sociometric status in schools without a transition during sixth grade than in schools with a transition. Collectively, these findings suggest that risk for involvement in bullying may be elevated in schools that do not have a transition to middle school. They also bring into question the conventional view of the small K-8 or K-12 rural school as a peaceful and supportive peer community.