This chapter suggests that Edgar Allan Poe’s complex relationship with Boston informed his ambivalent stance on American Transcendentalism, a literary and aesthetic movement he frequently criticized. Although Poe publicly disparaged the “Frogpondians” and ridiculed their emphasis on didacticism and pseudo-philosophy, his work reveals a multifaceted engagement with the core tenets of transcendental thought. While Poe often distanced himself from his Bostonian roots, he never fully severed ties with the city or its intellectual culture. His earliest publication, Tamerlane and Other Poems, was attributed merely to “a Bostonian,” signaling Poe’s early and complicated identification with the literary capital of New England. This chapter argues that Poe tells two “tales” of Transcendentalism: one overt and one covert. The overt tale comprises Poe’s public critiques and literary satires of key figures like Emerson and Fuller. The covert tale, by contrast, surfaces in private letters and fiction that flirt with Transcendentalist themes such as intuition, spiritual unity, and ideal beauty. This chapter posits that Poe’s failure to identify as either an idealist or a materialist, as well as his idiosyncratic use of the notion of “unparticled matter,” helps him carve out a space beyond this binary to create his own, independent metaphysical vision.