This paper shows how the legacy of Jane Addams' socialized education can live on in today's progressive education, especially in the digital age. Discussion is drawn from a case study of an anti-underage drinking campaign conducted by urban youth of color in an afterschool program. The media ecology environment in the campaign--the integrated usage of new and traditional media--enriched the way the youth made sense of experience and communicated with the world. The campaign led youth to learn more about other important issues, culture, and community history. Another critical element of the campaign's success was the active participatory culture of local community organizations and businesses, which formed an extensive support network for the youth's engagement. This case suggests that the synergistic relationship between new media ecology and connected learning environments can make progressive education more promising in the digital age.