The objective of this study was to evaluate whether dietary habits at age 2 associate with sleep duration trajectories through age 5 in children from north and central Appalachia. A total of 559 children from the Center for Oral Health Research in Appalachia (COHRA) cohort 2 were followed via caregiver phone interviews up to six times between ages 2 and 5. Exposures included data from the year 2 interview: sleep habits, household and demographic characteristics, meal patterns and consumption frequencies of fruits, vegetables, water, juice, milk, and soda. Sleep duration trajectories were identified using group-based trajectory models from ages 2 to 5. Three distinct nightly sleep duration trajectories were identified: short, increasing duration (4.5% of the study population); steady, 9 h of sleep (37.3%); and longer, slightly decreasing sleep duration (58.2%). Using multinomial logistic models that accounted for confounders, children with consistent meal patterns (i.e., meals and snacks at same time every day) and with higher fruit and vegetable consumption were more likely to follow the longer duration sleep trajectory compared to the steady sleep trajectory. In contrast, children who drank milk more frequently at age 2 were less likely to be in the longer duration sleep trajectory than the steady sleep trajectory.