Entering middle school can cause apprehension for young adolescents who face many cognitive, physical, social, and emotional changes. A quantitative, descriptive study was designed to identify and explain the concerns of rising sixth graders (n = 225) regarding their transition to the middle grades. Survey data were analyzed with regard to gender, race, and school type (i.e., inner city, urban, suburban, and rural). Undressing in front of others for P.E. was the most frequently rated area of high concern. There was a significant effect of gender on the level of concern for getting lost, changing clothes for P.E., peer pressure, being bullied, and academic performance. There was a significant effect of race on the level of concern for using a locker, having enough time to eat lunch, and going to the restroom. There was a significant effect of school type on the level of concern for making friends, belonging to the right clubs and groups, getting lost, having enough time to eat lunch, going to the restroom, and new school rules. Findings suggest at least a moderate level of concern by most fifth graders regarding various issues associated with middle school transitions, thus confirming the need for special programs to assist new students in acclimating to these changes and further research to determine their impacts.