This article draws upon the work of Timothy Morton and Slavoj Žižek in order to critically examine how mountain bike trail builders orientated themselves within nature relations. Beginning with a discussion of the key ontological differences between Morton’s object-oriented ontology and Žižek’s blend of Hegelian-Lacanianism, we explore how Morton’s dark ecology and Žižek’s account of the radical contingency of nature, can offer parallel paths to achieving an ecological awareness that neither idealises nor mythologises nature, but instead, acknowledges its strange and contingent form. Empirically, we support this theoretical approach in interviews with twenty mountain bike trail builders. These interviews depicted an approach to trail building that was ambivalently formed in/with the contingency of nature. In doing so, the trail builders acted with a sense of temporal awareness that accepted the radical openness of nature, presenting a ‘symbolic framework’ that was amiable to nature’s ambivalent, strange and contingent form. In conclusion, we argue that we should not lose sight of the ambivalences and strange surprises that emanate from our collective and unpredictable attempts to symbolize nature and that such knowledge can coincide with Morton’s ‘dark ecology’ – an ecological awareness that remains radically open to our ecological existence.