This paper describes a novel method combining speculative design with walking workshops to reveal the ethical and social challenges of connected technology in public spaces for policymaking. In the digitally hyper-connected society, digital technologies such as sensors, the Internet of Things (IoT), and Artificial intelligence (AI) enable people, and ordinary objects, to be connected in almost every place. This project tested different methods such as a walking method called walkshop and digital recreation of the physical environment to allow policymakers to explore a future con-nected place. We introduce a comparative analysis to show the opportuni-ties and challenges of both physical and digital methods. The findings show the value of physical and virtual walkshops to engage communities and place managers on building a connected place in a participatory manner.