Abstract: Following “Preface to Inauspicious Star”(December 1925), which marks the moment of “becoming conscious” of the essay, Sequel to Inauspicious Star, the collection of Lu Xun’s essays of 1926, displays a heightened degree of complexity, diversity and experimentality in style, genre and aesthetics. Corresponding to this development is Lu Xun’s second “wandering years” through Xiamen, Guangzhou and Shanghai, during the time of which his essay production underwent a process of radical expansion at imagistic, syntactic, discursive and stylistic registers. By focusing on his letter writing of this period, this article analyzes a double-movement, namely, the withdrawal into inwardness and an external playfulness, which produces a new literary intensity in aesthetic autonomy and social allegory. By naming this transitional style of Lu Xun “the road essay”, the author seeks a critical entry point into examining the “second birth” of Lu Xun literature. By analyzing the poetic constitution of this group of letters from on the road, the author argues that they form a joint in the transition of Lu Xun’s essay production from a state of “self-consciousness” to that of “freedom,” which is defined by its critical and representation engagement with history and politics.