To investigate maternal characteristics associated with breastfeeding initiation, we used data collected at baseline from mothers enrolled in the Mothers’ Outcomes After Delivery (MOAD) study, a longitudinal cohort study of maternal health after childbirth. We hypothesized that rates of breastfeeding initiation would be lower for cesarean versus vaginal births. We further hypothesized that breastfeeding initiation would be consistent across all births for multiparous women. Our broader aims were to identify maternal demographic and obstetrical characteristics associated with breastfeeding and to examine patterns of breastfeeding initiation across multiple pregnancies in multiparous women.