Background: Early initiation of breastfeeding (EIBF) within the first hour of birth is crucial for neonatal health and survival. Despite global recommendations, EIBF rates remain suboptimal due to various maternal, medical, and environmental factors. Objective: This study aimed to identify barriers to early initiation of breastfeeding among healthy late preterm and term infants in a tertiary care hospital in Himachal Pradesh, India. Methods: A prospective observational study was conducted from November 2022 to October 2023. A total of 1,020 mother-infant dyads were enrolled, and data were collected at the time of discharge. Statistical analysis was performed using SPSS version 17, with chi-square tests used to determine associations between breastfeeding initiation and maternal factors. Results: Among the participants, 66.1% initiated breastfeeding within one hour of birth, while 33.9% had delayed initiation. The most common reasons for delayed breastfeeding included time taken for postnatal transfer (41%) and delayed milk production (40.1%). Other significant factors included maternal discomfort (11.5%), difficulty with positioning/attachment (2.6%), and anatomical challenges such as flat or inverted nipples (1.7%). Early initiation was significantly associated with maternal age (p = 0.003), education level (p = 0.006), and occupation (p = 0.010). Mode of delivery and peripartum complications also had a significant impact (p = 0.001), with cesarean deliveries contributing to delays. Conclusion: While breastfeeding initiation rates in the study population were higher than national averages, logistical barriers, maternal discomfort, and cesarean deliveries contributed to delays. Strengthening postnatal support, improving breastfeeding education, and addressing hospital-related delays can further enhance EIBF rates.