Children attending Head Start suffer obesity at even higher rates than the national average of children within the same age range. With past research suggesting that as children age, the probability of childhood overweight persisting into adulthood increases from approximately 25% at age 4 to approximately 80% by late adolescence, and with one in seven low-income preschool-aged children being obese, identifying the risk factors at an early age is imperative to developing necessary interventions to reverse the disease. The purpose of this study was to investigate the risk factors that influence childhood overweight and obesity in Head Start and Early Head Start children and their families. Data were collected from 195 Head Start participants and their caregivers. These data included height and weight, eating patterns, physical activity levels, parental/guardian perceptions on weight, household socio-economic status and participation in federal assistance programs. The risk factors of childhood overweight/obesity were identified using chi-square tests, t-tests, and logistic regression. A strong significant relationship was found between doctors’ and health professionals’ weight advice and child BMI status (χ2 statistic = 17.494, p = 0.001). There was a significant relationship found between caregivers’ perceptions of their children’s weight and child BMI status (χ2 statistic = 22.4, p = 0.000) Also, there was a significant relationship found between caregiver educational attainment and child BMI status (χ2 statistic = 8.016, p = 0.046). In this investigation of the risks factors for childhood obesity in Head Start and Early Head Start Children several conclusions were drawn, caregivers with some college or trade school education were more likely to have normal BMI children, they were more likely to perceive their overweight or obese children as normal, and doctors and health professionals were more likely to classify normal overweight/obese children as normal weight.