ABSTRACT This article is an ethnographic account of searches for play space in Newcastle, Australia, specifically for skateboarding. Street skateboarding is predicated on unstructured play at ‘found’ spots in the urban landscape assembled from surfaces, objects, and obstacles. Without access to established skateparks during COVID-19 lockdowns, the search for play space became an exciting part of lockdown life, and street trees were surprising guideposts for locating unpredictable surfaces and angles. Through these observations, this article explores the potential of street trees in generating play space through skateboarding, making three arguments. First, street trees are overlooked as potential play space compared to trees living in parks, reserves, and playgrounds. Crucially, street trees generate play space by assembling and re-assembling the urban landscape in unpredictable ways. Second, skateboarders and trees are unexpected allies in unstructured play and the disruption of urban order. Third, street trees produce skate spots by modifying the built environment, challenging ideas of mutually exclusive realms of nature vs. city, grey vs. green, play vs. passivity, and use vs. misuse. These examples may not fit idealised notions of human-tree relations, but they open new possibilities for thinking about these relations and where we seek and find play space.