This article (visual essay) provides a glimpse of a field trip ventured by design students as part of a larger study of developing a localised version of design education for sustainability, focusing on the wants and needs of non-urban populations in vast Russian hinterlands. The central goal is to introduce would-be designers to the concepts of locally appropriate technology and sustainable/circular living by real-life examples and, eventually, teach them to recognise the sustainable potential of place-based technologies and practices of their making, using and maintaining. The primary data came from the trip to Pozhva, a village in Permskiy Krai, Russia, that gained popularity among DIY activists and users of off-road vehicles in Russia in the early 2000s because of its unique, community-centred manufacture of lightweight ATVs on low-pressure tires, nicknamed “jeeps”. This article presents the students’ journey in a comic strip portraying a composite character of technologies and their user-designers as experts in local conditions and (subconsciously) agents of circularity. The article closes with a discussion on the expedition’s discoveries and learning outcomes, correlating them with broader implications for design education.