The objective of this study was to compare breastfeeding, postpartum mental health, and health service utilization between a group of late preterm (LP) maternal infant pairs and term counterparts. Data was drawn from a prospective community-based cohort in Calgary, Alberta. Bivariate and multivariable analyses were performed. LP infants were more likely to have had a longer median length of stay after birth (P < 0.001) and a higher re-hospitalization rate at 4-months (P < 0.001) compared to term infants. Mothers of LP infants were more likely to report immediate breastfeeding difficulties (P < 0.001) and earlier cessation of breastfeeding at 4-months postpartum (P = 0.008). Multivariable analyses revealed that LP status was an independent risk factor for excessive symptoms of maternal anxiety (OR = 2.07; 95 % CI = 1.08,3.98), but not for depression, stress, or low parenting morale. LP infants and their families are a vulnerable population with unique developmental trajectories. Further longitudinal research is required.