H. D. Thoreau’s Walden has often been found in the midst of political, cultural, or, more recently, ecological controversy due to the frequent reading of his text as a practically-oriented guidebook for self-improvement towards an ultimate goal of creating the perfect natural man in a “utopia of one.” This paper examines some unfortunate consequences of this reading of Walden, as well as possible reasons for the historical resistance to alternative, artistic, romantic readings of the work in the hope of elucidating some of the hidden strengths behind the often glaring inadequacies of the book, which were lamentably obvious to his contemporaries and subsequent generations of critics. This paper also draws attention to the innovative, Romantic side of Thoreau which is commonly obscured by such practical, political or even nationalistic representations of Walden. The paper concludes with the assertion that Thoreau was able to effect a marriage of the Romantic and the Rationalistic, which had been so crudely and acrimoniously divorced by the uncompromising, revolutionary rhetoric associated with the idealism of early Romanticism. Thus, Thoreau is able to reinvigorate the Romantic outlook and contribute towards its partial survival into periods dominated by Realism and Modernism.