In the classrooms across the world the Transcendentalism is still being reduced to a sterile and benign literary movement, which has practically alone"built" authentic American literature. The following article attempts to broaden the milieu in which the Transcendentalism is being discussed with the analysis of other, political side of the Transcendentalism's short epoch, and above all to illuminate its contribution to the political philosophy and practice of progressive movements in the US. The author makes an attempt to show and prove that the Transcendentalism should not be treated only as a literary movement, but also as a philosophical and even political one. The Transcendentalists' battle against the "Puritan Leviathan" was not fought onlyin literature - with breaking the rules of the structure and contents of literary works, but also in everyday life - e.g., with non-conformism, de-etatism, feminism, abolitionism, civil disobedience. The Transcendentalism is not only one of the main inspirations and aspirations of the new anarchism in the US, but also the first manifestation of anarchism of everyday life or "lifestyle-anarchism".