In this essay, we examine poignant moments that arose while walking the approximately 80 km Hoerikwaggo Trail linking the Cape of Good Hope to the city of Cape Town, South Africa. Our walks, styled as walking seminars, started in 2013. Two local and global events have resonated strongly with the walking seminar project, and have lent a sense of urgency to the debates and experiences on the trail: the events of #RhodesMustFall in 2014, and those of #DayZero 2018. The narrative arc of this essay is plotted along moments described as in a diary: each day explores a set of ideas. As such, we think through the landscape's history as a breathing, material presence that both burdens the present and acts as a kind of birthright. Finally, we posit that walking the Hoerikwaggo Trail can be understood as one way of navigating what Ann Laura Stoler refers to as the "imperial debris" of the mountain.