In response to the spread of SARS-CoV-2 across North America in early March of 2020, Canadian and United States medical schools swiftly virtualized medical education for pre-clerkship students. With remote learning arrived novel challenges: barriers to students’ comprehension of course material, difficulties conveying the nuances of patient interaction, and social hardships hindering students’ continued progress. The 2020 Harvard-McGill Medical Student Exchange, a group of ten McGill University Faculty of Medicine and Harvard Medical School students, analyzed their institutions’ respective responses in the virtualization of medical education and their personal experiences with remote pre-clerkship education. The authors’ work provides insight into opportunities for mutual progress and cross-cultural exchange between Canadian and American medical schools, in the context of the COVID-19 pandemic. The authors detail potential changes to didactics, student research opportunities, support for students, and clerkship preparation that they expect would benefit pre-clerkship students in an ever-changing biomedical landscape. With gratitude toward their respective programs for their efforts in transitioning to virtual learning, the authors look toward a future of medical education increasingly interwoven with digital technology and responsive to social change.