With age, alterations occurring in bone quality, quantity, and microarchitecture affect the resistance of trabecular bone to local failure. The clinical implications of these changes are evident by the observed exponential increase in fracture incidence with age. Although age-related development of skeletal fragility is well established, it is unclear how the local failure properties of bone change with age. We previously reported a specimen-specific technique to assess microstructural stresses and strains associated with microdamage initiation but did not assess age-related changes. In this study, we compared younger (average age 2 years) and older (average age 10 years) bovine trabecular bone to evaluate how alterations in bovine bone quantity and quality with age affect the local mechanical environment associated with microdamage formation. The results show strong positive correlations between microdamage and local stresses and strains for both younger and older bovine trabecular bone. Correlation strength was slightly improved (< 8%) for some parameters by incorporating heterogeneous local material properties based on mineral density into the finite element models. Within individual trabeculae, average stresses and strains were significantly higher in microdamaged trabeculae compared to randomly selected undamaged trabeculae, regardless of age. However, damaged trabeculae in older bone were found to have higher stresses and lower strains than those from younger bone. Corresponding differences in mineral density, microarchitecture, and FEM-determined local material properties were also observed between the two groups. Taken together, these data suggest marked age-related changes in the mechanics of microdamage initiation at the trabecular level. The combined experimental, computational, and histochemical approaches used in this study provide an improved understanding of microdamage initiation and bone quality.