Initiated during COVID, this research utilizes material autoethnographic methods to study the video games Gris, Journey, and Season: Letter to the Future. This thesis contributes to 1) the debates in pilgrimage and cyberpilgrimage around the validity of a pilgrimage not physically taken, 2) the potential of a relationship between games and pilgrimage and what that reveals about both mediums, and 3) offering tools to game designers looking to replicate the emotional experiences felt in each of the games played, asking: what do video games as a medium afford pilgrimage, what does pilgrimage offer journeying games, and what can we learn about digital journeying through their comparison? Is playing a video game the same as doing a terrestrial pilgrimage? This work concludes that playing a video game is not the same as doing a terrestrial pilgrimage, but that it has specific affordances and constraints which make it affective due to the way it attends to the body, senses, material, locality, and everyday. It is a counter-argument to the idea that both play and cyberpilgrimage are disembodied. Games afford a unique kind of experience and transformation for undertaking pilgrimage, and pilgrimages afford a unique kind of play. As such, to ask at what pilgrimage and games can afford each other is not to assert dominance (or homogeneity) between terrestrial and cyber- pilgrimage, but rather to ask at large: What are the varieties of meaning derived from different forms of pilgrimage and what brings them about?