Maharshi Dhondo Keshav Karve, an Indian social reformer, and the pioneer of widow education, has been a prominent figure in improving the status of widows in India. Not only did he assist in breaking the age-old stereotypes by advocating widow re-marriage, promoting education facilities but himself married a widow. Likewise, he also established Maharshi Karve Stree Shikshan Samsta, an Indian Education Society, in 1896 Indian Education Society to promote Women's education. In the same year, Karve started “Home for widows” and a school for widows in a small village named "Hingane" in Pune. He was also accorded with the highest civilian award, the Bharat Ratna, in 1958 by the Government of India. In this context, the research paper focuses upon the glimpses of Maharshi Karve life as a social reformer, his struggle in advocating widow education and their remarriage in a regional texts, Himalayachi Savali (The Shadow of Himalayas) by Vasant Kanetkar and Maharshi Dhondo Keshav Karve by Dr. Neela Pandhare. Being an adaptation of Karve’s life, both the texts depict the conflict between Karve’s ideology and the constraints of social entanglements. The paper attempts to explore the transformation of the protagonist who breaks the stereotypical shackles from a feminist standpoint.