The number of children who are obese and overweight continues as a public health challenge despite decades of research. The purpose of this article is to describe trends in body mass index (BMI) percentile data collected from 11- to 14-year-old school children in 2008-2009 and 2015-2016 in rural Wisconsin. The BMI percentiles from 1,347 students were compared using time, gender, age, and school (public vs. parochial) as predictors. The trend over time indicated a decrease in students of healthy weight and an increase in those overweight or obese. Also noted was a significantly higher proportion of children who were overweight or obese in parochial compared to public schools. Discussed are the observed trends, community-wide initiatives implemented, as well as how schools can employ a more comprehensive approach to childhood obesity that first ensures community readiness and involves school, home, and community.