This chapter illustrates the activist potential of community media through two major digital storytelling projects spearheaded by Vanessa Pabón in Springfield, Massachusetts: Telling Our Legacies Digitally (TOLD) and the Latino Youth Media Institute (LYMI). Digital stories are generally understood as a two- to five-minute recorded voiceover illustrated with still images or video in which the author recounts a significant episode in her or his life story. Across the country, a number of community media and digital storytelling projects specifically target Latina/o communities in ways that both overlap and differ from the brand of media activism that TOLD/LYMI practice. The chapter discusses the concrete TOLD/LYMI initiatives carried out in partnership with entities and individuals that play a role in establishing, maintaining, and expanding the organization’s physical, human, and virtual outreach. Successful community media initiatives collaboratively create inclusive and multimedia/multimodal products that can be shared with different audiences and for various purposes across multiple media formats and physical settings.