This anthropological and archaeological study was an investigation of medicine use in the American Victorian era (1876-1915) and the Progressive era (1900-1920) in San Diego, California. The glass assemblage of the Whaley House was compared to artifact collections from six features within four San Diego County sites (the Theosophical Society, the Melting Pot, the Chinese American, and Nate Harrison sites). The former residents associated with the archaeological features of this study represented diverse socioeconomic and ethnic groups present in American Victorian and Progressive era San Diego. The data produced from the site cross-comparisons revealed unique characteristics of medicinal use of this time. Illness was treated with patent medicine (medicine sold without a prescription), prescription medicine (prescribed by a physician), and alternative medicine such as homeopathy and Traditional Chinese Medicine. The legacy of the Greek Hippocratic medicine survived well into the twentieth century as evidenced by the use of Hippocratic language in patent medicine advertising along with the use of counter-irritants and purgatives. The consumption of prescription medicine was greater in upper socioeconomic groups and patent medicine use spanned across all socioeconomic groups. This study demonstrated the reasons behind consumer's medicinal choices, provided an overview of the economic and social systems, and highlighted the dynamics of acculturation, assimilation, and cultural diffusion during the turn of the twentieth century.