Analysis of endocannabinoids (ECs) and endocannabinoid-related compounds (ERCs) in hair is assumed to retrospectively assess long-term EC/ERC concentrations. To inform their use, this study investigated stability of EC/ERC hair concentrations in mothers, fathers, and their children across the perinatal period as well as associations between family members. In a prospective cohort study, EC (AEA, 1-AG/2-AG) and ERC (SEA, PEA, OEA) levels were quantified in hair samples taken four times in mothers (n =336) and their partners (n = 225) from pregnancy to two years postpartum and in offspring (n = 319) from shortly after birth to two years postpartum. Across the perinatal period, maternal and paternal hair ECs/ERCs showed fair-to-good multiple-test consistency and variable relative stability, and inconsistent absolute stability for mothers. Regarding children, hair ECs/ERCs evidenced poor multiple-test consistency, no absolute stability, and either no or variable relative stability. Hair ECs/ERCs were significantly related across the perinatal period within couples and parent-child dyads. Findings suggest hair ECs/ERCs during the perinatal period possess some trait-like stability in adults, highlighting the utility of hair analysis. The first two years of life may be a dynamic phase for the endocannabinoid system in children, potentially characterized by endocannabinoid system synchrony within the family.