Drawing on extensive empirical evidence gathered at British music festivals and from ethnographic research with British tourists on the Balearic island of Ibiza, this chapter aims to provide an in-depth appreciation of the nature, extent and situated meaning of poly-drug use within bounded spectacular events. For many young people, music festivals and holidays represent a window of freedom, experimentation, transgression and transformation. As many of the usual rules and restrictions of everyday life are temporarily suspended, these spectacular events can be characterised by dramatic changes in usual patterns of consumption and leisure. We argue that the framing of some festivals as transformative, by festival production and festival-goers, can be likened to the fairy-tale narrative of a journey ‘into the woods’, where protagonists are plunged into strange new worlds before returning home with heroic stories to share (Yorke, 2013, p. xi). The chapter, structured around this journey metaphor, focuses on the relationship between poly-drug consumption and three inter-related dimensions of the event, as identified by Getz (2008, p. 414): motivation and expectations; the lived experience of ‘being there’; and reflections on meaning and influences on future behaviour. The chapter concludes with implications for policy, practice and research. We argue that if young people are to emerge from the ‘woods’ unscathed, there is an urgent need to understand this temporal transgression and embed innovative harm reduction strategies within music festivals, tourist resorts and other spectacular spaces that can distort patterns of drug and alcohol use.