The transition away from car-centrism to multi-modality in U.S cities and the integration of emerging trends and technologies such as smart cities, vehicle autonomy, and a shared economy, are all increasing the complexities and require new methods for city planning. Thus, Digital Twins (DTs), Virtual Reality (VR) and Augmented Reality (AR) arise as low-cost effective tools to ideate, simulate and test street designs that allow Design Researchers and Industrial Designers to use them during co-design workshops with expert stakeholders (Barricelli et al., 2019; Pidel et al, 2020) in which qualitative insights are gathered on specific areas of the current infrastructure. These insights can be framed in future brainstorming / co-design sessions and translated into tangible design recommendations for the city. This paper provides a brief synopsis of the shifting paradigm in cities, and the use of new technologies in the field of design research to simulate scenarios and inform stakeholder decision making. We then expose a case study of our co-design workshop where we present a DT concept of a chosen intersection in Cincinnati to city government stakeholders and attain their qualitative feedback on the vision for the area.