Smart cities carry the burden of utilizing technologies to support city life during and beyond the Covid-19 pandemic. More than ever, true smartness needs to address the broader health implications of the shared urban space. Especially highly populated cities tend to suffer more from the consequences of Covid-19 than rural areas. Without a doubt, the pandemic has revealed particular weaknesses of the existing urban environment, in urban space and population demographics, so evident of unprepared city infrastructure systems. The traditional design of public space has created inequalities, and such space design serves the needs of a commercialized urban context and enables public gatherings or private/commercial access. The sudden behavioral shift needed in cities means that smart solutions are also needed for the health and well-being of city populations. This paper examines the impact in the urban environments for London, Manchester, Newcastle, and Liverpool. This paper maps the implications of physical distancing due to Covid-19 using cases studies in three main areas: i) roads, ii) parks, and iii) retail. A matrix of urban, social, and health consequences is suggested, which will shape urban policy. It will focus on terms of access and use of urban space during the pandemic and beyond. The expected outcome of this research is to map some of the metropolitan area to demonstrate restrictions, changes in sharing behavior, and gamification opportunities of urban space. The expected outcomes will provide evidence-based scenarios for gamification technologies (for example, wayfinding, location, and character-based) of the challenged urban space in roads, parks, and retail to support change in future policy. The paper will discuss the implications of behavior change and consider so-called “gamification” practices in the urban space, using examples of social distancing, movement tracing, and techniques that add to a truly smart city. Overall, the aim is to demonstrate the spatial constraints of Covid-19; social distancing as the main challenge and to explore how the design of urban form and smart systems will provide for a healthy and resilient urban environment. This research addresses good urban health and a playful approach to the new way of urban living.