In humans, breastfeeding and weaning depend on the infant’s needs and physiology but are also influenced by environmental and cultural factors. While infant feeding strategies vary across different regions and historical eras, the associated transition from breastmilk to solid foods is universally thought to be stressful. However, still little is known about infant feeding practices and possibly associated stress in former times. This also applies to the period of transition from classical antiquity to medieval times, which shaped modern Western civilization. To enhance the understanding of childhood nutrition and stress during this period, we first analyzed stable carbon and nitrogen isotopes in serial dentine samples from the first molars of 38 individuals buried in the region once known as the Roman frontier province of Raetia secunda, now encompassing Southern Bavaria. In addition, we investigated the presence of linear enamel hypoplasia (LEH), known to be a marker of unspecific physiological stress, within their dentition. We used this data to create isotope profiles that display dietary changes in comparison with the occurrence of LEH. We found highly variable δ15N and δ13C values and different shapes of isotope profiles which indicate different nutrition of breastfeeding individuals, complementary foods and post-weaning diets, and individual weaning patterns. For most individuals, the weaning process was completed between the ages of two and three. Interestingly, some females of non-local origin show longer weaning periods, likely displaying the influence of different cultural practices in other communities. We also found that LEH most frequently occurred in the post-weaning phase, which supports the assumption that children were at increased risk once breastfeeding had ceased completely. Furthermore, a change in the post-weaning diet in the seventh century coincided with an increased prevalence of LEH, indicating that the foods chosen or available during this time affected the susceptibility of children to stress. In conclusion, our study unveiled diverse infant feeding strategies practiced across various communities, both in different historical eras and geographical locations.