With the rapid adoption of telemedicine since the COVID-19 pandemic, it has become imperative to teach and evaluate health professional trainees on skills important to conducting effective virtual visits. We developed a simulation-based workshop with (1) readings, (2) a lecture covering online communication and the virtual head and neck exam, (3) a telemedicine simulation with a standardized patient observed by faculty, (4) personalized feedback from faculty, and (5) a group debrief session. We created an evaluation rubric based on three of 20 Association of American Medical Colleges (AAMC) telemedicine competencies to assess learner performance during the simulations. Students (medical and physician assistant students; n = 50), and internal medicine residents (n = 20) completed this workshop in 2023. At least 90% of trainees across the two groups were rated as approaching entrustment or entrustable in each competency. This workshop is an example of a scalable telemedicine curriculum that can be used to teach and evaluate learners in the virtual physical exam across the training continuum.