In this paper I offered to reread Orlando: A Biography and its lesbian, queer, and trans receptions by addressing the epistemological issue of anachronism. Exploring how both Woolf’s novel and its critical and mainstream receptions have been informed by the ever-shifting paradigms of gender and sexuality for decades now, I retraced the multiple and at times conflicting interpretations the text has generated in order to question the so-called limits of anachronism and to highlight the generative tension between historicity, contemporaneity, and anachronism. Articulating feminist, queer, and reception studies, I ultimately endeavoured to lay the ground for a heuristics of anachronistic reading which aims at enabling readers to navigate their way from their very own “Present Time” to Woolf’s and Orlando’s, and back again.