This study explores how grassroots social innovations can challenge traditional educational paradigms in India by contextualizing literacy methodologies. Using a comparative qualitative case study design, it examines two initiatives: the Digital Empowerment Foundation (DEF) and Jodo Gyan. The research draws on secondary data sources, including interviews, organizational documents, and program reports. The first case, DEF, promotes community-based digital education through grassroots digital centers, fostering digital access, civic participation, and socioeconomic inclusion. The second case, Jodo Gyan, applies constructivist classroom practices in mathematics education, replacing rote learning with hands-on, inquiry-based approaches that connect learning to everyday experiences. A comparative analysis reveals that while DEF primarily addresses digital exclusion and socioeconomic marginalization, Jodo Gyan targets pedagogical reform within formal education. Both initiatives extend the concept of literacy beyond textual skills, embedding learning within local contexts and social relationships. Together, they illustrate how social capital and constructivist learning frameworks can inform inclusive, scalable, and context-sensitive education models. The findings highlight the critical role of community agency in driving sustainable educational change.