In this chapter we explore the pedagogical effects of collective movement on bicycles grounded in our direct experiences, personal reflections, group discussions and the notes we took during a trans-European, self-organized educational activity called Cycling Alternatives in 2013 and 2014. We thereby engage with non-representational and post-foundational anarchist thinking and geography field trip didactics while arguing that we were practicing machinic field trips that operated as collective unlearning experiences. Thus we were gauging dominant scripts in-between us and encouraging each other to embrace the potentials of collective action. We thereby quasi-naturally experimented with anarchist principles, like consensus decision making, and were moving towards emerging socialities. In short, our cycling machine ‘taught’ us anarchy without teaching it, a pedagogy that did not know how to teach. Not least, we hope our experiences inspire others to embrace radical pedagogies within the disciplining matrix of geography and beyond.