This paper explores how Wordsworth’s “The Ruined Cottage” embodies and directs the course that Romantic poetry will take, predating his poetic world, the meaning of his poetry, and the essence of poetic theory proclaimed in the Preface to his poetry collection, Lyrical Ballads. In doing so, this paper shall focus on the representation of nature and suffering, considering the dramatic frame as the focal point through which we can glimpse the transformation of Wordsworth’s thought. In “The Ruined Cottage” Wordsworth chooses an ordinary person, Margaret, as the subject matter for a tragic poem, and undertakes the work of mourning. This approach overturns or deviates from the dominant principles of Neo-classicism, allowing Wordsworth to implement his empathy for common people within the realms of literature and criticism. I shall argue that this choice represents novelty and poetic experimentation, serving as a revolutionary declaration about poetry, and impling a subdued form of political engagement. The attitude towards nature and humanity displayed by the wandering peddler and his meditative mind is similar to Wordsworth's perception of nature and humanity revealed through the ruined monastery in “Tintern Abbey”.