This chapter aims to shed light on the discourse of skiing and Swedishness in three winter picturebooks and one illustrated book. The argument is that these books both reflect and create skiing as a national sport. A geographical setting can produce connotations to a specific climate and landscape, but for a nation-state to become a meaningful place—an “imagined community”—it will have to be associated with certain culturally coded ways of being and acting in response to the physical world. In a Swedish context, skiing provides the “Swedishness” of the place/nation. The main examples under scrutiny are Elsa Beskow’s Olle skidfärd (Olle’s Ski Trip) from 1907, a winter fantasy with strong nationalist connotations; further, Bertil Almqvist’s Barna Hedenhös Vinterresa (The Winter Journey of the Hedenhös Children) (1958), which rewrites the nationalist agenda as a story of technical and social progress; and finally Tove Jansson’s two related texts, Moominland Midwinter (1957) and the comic strip “Moomin’s Winter Follies,” in which Jansson subverts some of the prevalent skiing and winter sports stereotypes, are examined. While these narratives (and many others) are about skiing, layers of meaning are added over time (like snow), none of which vanish completely. In the three iterations we see in the chapter, skiing is associated with nationalist winter fantasy, utopian progress, and comic subversion.