As the world locked down in the 2019 Spring term, what seemed like a short-term adjustment to digital synchronous and asynchronous course delivery soon became a longer-term modality, ultimately re-shaping the entire following academic year. Since then, pedagogical shifts to digital platform options facilitated classroom learning for those unable to attend in person. In step and perhaps more so than ever, the past academic year has proven not only that digital teaching can extend far beyond the classroom, but also that community engagement can be successfully accomplished in meaningful ways, despite social distancing measures, to enable students to learn sought-after and up-to-date methodologies and practices that increase student sensibilities and awareness of the web of issues surrounding community design, particularly in the face of climate challenges. In the 2020 Fall term, the non-profit ReMain Nantucket began conversations with faculty members from various universities to frame a multi-institutional and interdisciplinary effort to connect community experts and residents to academics and their students to each other, collectively addressing the growing climate challenges facing the town of Nantucket, Massachusetts.