Using traditional and innovative osteological methods, skeletal degeneration and bone strength were assessed. The aims of the research were to analyze patterns of aging and differences in the manifestation of degeneration by sex, body size, and lifestyle. Two skeletal samples from medieval and post-medieval Denmark were analyzed for disorders associated with aging and increased body mass, the rural cemetery of Tirup (12th – 14th C.) and the urban cemetery of Black Friars (13th – 17th C.). This was a time of significant socioeconomic, environmental, and residential transition. During the medieval period Christianity replaced the old Viking Pagan religions, urbanization increased, the climatic downturn of the Little Ice Age affected crop yields and food security, and infectious disease, specifically the Black Death epidemic, decimated the population. Recognizing the effects of age, sex, and socioeconomic status on the health experience of Danes as they lived through these changes is important to understanding life in medieval and post-medieval Denmark. By analyzing trends in stature, body mass, femoral robusticity, and indulgence- and age-related degeneration, the results suggest that individuals living in the rural area were healthier than those living in the urban area. The results also present a temporal trend towards decreasing health from the medieval to the post-medieval period. The Protestant Reformation (1536 CE) seems to have affected urban females more significantly than males. Post-medieval female femoral strength increased significantly while male femoral strength remained constant. In an attempt to gain economic freedom in increasingly difficult times, many females sought employment in unconventional and physically demanding positions. Age-related health patterns are complex and multi-faceted. Using conventional methods for age-estimation may obscure patterns of aging in the oldest individuals. Using the more precise age-at-death estimates from transition analysis (Milner and Boldsen 2012a), the current research indicates that stature increased in older age categories (70 years-at-death), but tall stature was detrimental to extended longevity (past 70 years of age). This trend was paralleled by several age- and indulgence related disorders. This research provides a comprehensive examination of health and aging in medieval and post-medieval Denmark with specific reference to the burgeoning urbanization revolution and changing political, religious, and environmental climate.