Although Robert Frost has been known to sympathize with impoverished working class folks, his conservative political stance has rarely been indicated in the examination of his representative poem, “Stopping by Woods on a Snowy Evening.” As is revealed in some of his notes, he opposed the idea of collective political action on the part of the working class for fear that it might endanger American capitalism. This paper takes note of his conservative politics and argues that Frost’s political views are traced within one of his most famous poems, to specifically render the poem’s structural dichotomy unstable. Appropriating particular conceptual tools from Marx and Benjamin, this paper asserts and argues for a tension between the apparently straightforward narrative surface of the narrator’s aesthetic immersion and his possessive preoccupation with a matter of ownership. Reading this way, the narrator’s hesitancy seems inscribed with Frost’s political conservatism concerning the working-class impulse for bettering their given conditions of life.