The first wave of the COVID-19 pandemic that affected many cities around the world during the spring and summer 2020 was often met with regulations requiring people to lockdown, to quarantine or to respect social distancing. Urban spaces often became off-limits and depopulated, filled with borders isolating people confined at home. Nevertheless, in these trying times new forms of urban gamification surfaced, allowing citizens to engage their surroundings playfully, to connect with others and to escape these dire situations. In this paper, we propose an overview of the many playful activities that emerged in the cities hit by the pandemic, organised according to the urban borders they engage (windows, balconies, rooftops). We then focus on how several borders can be engaged by the same play practice, through a gamified application called Window Expeditions, which aims at participatory data generation, while addressing some of the issues related to isolation and reduced mobility of its users. In the conclusions, we discuss the potential role of urban gamification during the pandemic and, in particular, its ability to comfort, connect, increase curiosity and encourage exploration.