The Chinese poet Hsu Chih-Mo (1897-1931), known as the Chinese Shelley, brought Romantic ideas from Britain to modern China. His conviction of liberty was manifested in his literary works, alongside his pursuit of true love and social change. This essay employs the concept of “Romantic legacies” to revisit Hsu’s Romantic philosophy and Taiwan’s Romantic movements. Firstly, the essay examines Hsu’s Romantic legacies. Influenced by Bertrand Russell, Thomas Hardy and other British intellectuals, Hsu succeeded to Shelley’s Romantic ideas of social justice and love. His journeys to Europe and experience of love helped shape and reshape his Romantic philosophy. Secondly, the essay explores Hsu’s Romantic ideas and Taiwan’s democratization. Hsu’s literary works, regaining significance in the spirit of the Fourth May movement, facilitated Taiwanese youngsters’ understanding of the significance of independent minds. Hsu’s poetics of liberty was introduced to Taiwan and gained popularity, in particular, during the period of campus ballads. In brief, the Shelleyan skylark flew from Britain, via modern China, to Taiwan and continues singing its songs of idealism.