In the early twentieth century rumblings of resistance against the despotic Dogra rulers of the princely state of Jammu and Kashmir gained momentum, and Kashmiris sought to alter the social injustices and economic inequities that defined their lives. New dreams, new aspirations, and new self-consciousness signaled an awakening, a rejection of subjugation and a deep desire to seek out freedom. This chapter explores Kashmiri imaginings of freedom in this historical context. Poetry, pamphlets, and literary works reveal how Kashmiris adapted pre-existing themes of freedom to fit the needs of their deteriorating economic and political landscape. While politicians and intellectuals made speeches, edited and wrote for newspapers and magazines, and organized study circles where discussion often spilled over into activism, Kashmiri poets profoundly affected by the revolutionary fervor of the 1940s wrote inspiring poems to spark courage and resilience in Kashmiris fighting for their rights. In constructing ideas about freedom, politicians and poets alike liberally borrowed from the ancient texts and mystical culture of Kashmir, but also remained open to new international ideas that could, they felt, improve human relationships and lay foundations for a strong society. Despite some shared culture and interests, however, I further argue that the definition of “freedom” was not universally constant; in the changing socioeconomic context of the late nineteenth and early twentieth centuries, Kashmir's social divisions and religious differences added complexities to this discourse.