Thoughtful and intentional collaborations among small, community-curated museums, colleges, and schools have the potential to create transformative learning opportunities for all partners while also improving access to, and preservation of, museum collections. In this article, we describe the Digital Scholarship in Museum Partnerships (DSMP) project, a project designed to establish authentic, technology-enhanced educational experiences that forge synergistic relationships between college students, area museums and public school educators. We focus on the first of a series of collaborations between DSMP and the rural, volunteer-led museums in Kent County, Maryland. Through intentional collaboration, and on a next-to-nothing budget, project members digitized more than 4,000 objects, collected oral histories, created two middle-school unit plans, and built a virtual reality (VR) tour with more than 70 interactive buttons. Here, we describe the collaborative and planning processes, as well as the strengths and challenges of collaborations of this kind, in order to provide a road map for other museums and educators interested in doing similar work.