Opportunity to play can make a positive contribution across the life course. While successive amount of academic literature has shown how play can increase levels of physical and mental health for children, its ability of sustaining the quality of life into the older age has been dominated by a piecemeal age and gender specific approach (Mahdjoubi and Spencer, 2015). Action in actual urban design practice is still in infancy. This project addressed the gap. An extensive amount of liteature review demonstrated the rich potential of the older people’s opportunity to play in urban public realm and ‘active aging’ (WHO,2007) and ‘healthy aging’ (WHO, 2012). In order to encourage and respond to the innate needs of playfulness for older people more effectively, this project challenged the conventional approach- es to environmental design by introducing a more dynamic and richer typology of urban environment in forms of trails that can potentially encompass multiple play- ful elements.