People experiencing homelessness are disproportionately impacted by complications of skin and soft tissue conditions. A nonprofit street medicine organization developed a program of educational workshops seeking to enhance the informal care of skin and soft tissue conditions employed by people experiencing homelessness. This paper describes an evaluation of this program through written surveys and feedback sessions with people experiencing homelessness who attended these workshops. This evaluation aims to identify recommendations for program improvements and understand the experience and impacts of workshops. Additionally, this project included an assessment of the effectiveness of these and other methods for engagement among people experiencing homelessness to inform future work.