A wide range of pharmaceuticals and endocrine disrupting compounds enter freshwaters globally. As these contaminants are transported through aquatic food webs, understanding their impacts on both aquatic and terrestrial ecosystems remains a major challenge. Here, we provide the first direct evidence of the transfer of pharmaceuticals and endocrine disruptors through the aquatic–terrestrial habitat linkage by emerging aquatic insects. We also show that the type of insect metamorphosis and feeding behavior determine the bioaccumulation patterns of these contaminants. Adult Trichoptera, an important food source for riparian predators, showed an increased body burden of pharmaceuticals and endocrine disruptors. This implies that terrestrial predators, such as spiders, birds, and bats, are exposed to mixtures of pharmaceuticals and endocrine disruptors of aquatic origin, which may impact their physiology and population dynamics. Overall, our study provides valuable insights into the bioaccumulation patterns and trophic cross-ecosystem transfer of these contaminants, from aquatic primary producers to terrestrial predators.