Exploring the relationship between nutrition, skeletal development, and aging is important in maintaining bone health. Even further, understanding the complexity of skeletal homeostasis may assist in reducing the prevalence of skeletal disease, especially osteoporosis. The skeleton is unique in that it can adapt to various physical pressures, maintain shape, and remodel itself to increase integrity and strength. For decades, it was thought that increasing skeletal health was as simple as drinking three 8-oz. glasses of milk per day due to high levels of bioavailable calcium. New research into the bioactive components of milk have revealed other roles in promoting skeletal health. Milk contains various bioactive peptides, houses genetic information in milk-derived exosomes, and supplies relevant amounts of nutrients important for bone health. In this review, we discuss the basics of skeletal formation and homeostasis, dive into the potential effects of milk on the growing skeleton, and present contrasting findings.