Zhuangzi and Henry David Thoreau share a critical interest in the relations between wandering, nature, and experience. Their attitudes toward nature provide a basis for their views of human well-being, which in turn inform their attitudes toward language, society, and politics. Both celebrate nature as a source of constant novelty, change, and nourishing life. These values clash against social conformity and political homogeneity. For both Zhuangzi and Thoreau, how we experience life is already constitutive of human well-being. Wandering thus provides a unique vision of freedom, one that binds experience, nature, and social-political criticism.