Festival experiences and environments are often marketed as magical, an appeal that marks expanding Winter Cities initiatives to rebrand forbiddingly cold climates as attractions for tourists, residents and investors. Edmonton, Canada’s Flying Canoe Volant festival, named for a French-Canadian myth about a bewitched journey, offers ‘magic’ and ‘mystery’ over three February nights in a central urban ravine that attracts up to 40,000 participants each year in temperatures far below zero. A key quality of magic is transformation, and the ravine itself is part of a prior regeneration of early industrial zones that removed most traces of human habitation including by the city’s minority founding groups: francophones, Metis and Indigenous Peoples. These groups, in turn, are the focus and drivers of the festival on the edge of a recently heritage-branded ‘French Quarter’. This chapter considers themes of transformation in contexts of urban heritage, tourism and regeneration centred around a liminal urban space, cultural landscape or terrain vague. A central question is how green space as relatively undeveloped parkland cutting a deep groove through adjoining streets can contribute to goals of sustainable regeneration. As festival space, it fosters unpredictable, collaborative voices and community relations that endure beyond the event, with the important dimension of revisiting and recrafting certain entrenched historical narratives.