The Tokaido highway, connecting Edo with Kyoto, was the most vital thoroughfare in Japan. Its cultural presence in pre- to early modern Japanese society led to the publication of woodblock print series, such as the widely known landscape prints by Hiroshige, that took this famous road as their theme. The prints of Utagawa Kunisada, the most sought-after woodblock print designer of his day, represent a different treatment of the Tokaido, in which popular kabuki actors in specific roles are paired with Tokaido post stations. This study discusses the phenomenon of serialization in Japanese prints outlining its marketing mechanisms and concepts. It then proceeds to unravel Kunisada’s pairings of post-stations and kabuki roles, which served as puzzles for his audience to decipher. Finally, this study analyses Kunisada’s methods when he invented and developed these patterns. Kunisada’s Tokaido is a valuable visual source for the print collector, illustrating over 700 prints and it has been selected for an Honorable Mention at the 2014 IFPDA (International Fine Print Dealers Association) Book Award.