Abstract This article offers a new reading of Lewis Carroll’s Alice’s Adventures in Wonderland and Through the Looking-Glass, proposing that Alice’s journey is an illustration of the process of learning to read. Using metrics, including mean length of utterance, lexical profiling, and the Gunning Fog Index, this study evaluates the linguistic progression of Alice’s utterances and their readability to trace parallels between her experiences and the stages of reading development: pictorial, phonological, and orthographic. Alice in Wonderland symbolizes a “pre-reading” phase, while Through the Looking-Glass represents her progression into reading fluency and meta-linguistic play showcasing how Carroll, who reportedly struggled with reading himself, strategically designed the complexity of the text to align with the cognitive development of the reader. By combining literary analysis with computational tools, the study reveals the paradox of reading in Carroll’s work: a simultaneous breaking and following of linguistic norms. It may also enhance understanding of Carroll’s literary innovation in how his narratives mirrored the cognitive development of the reader and situate his work as a precursor of modern readability frameworks.