To mitigate the adverse impacts of COVID-19 on the restaurant industry, the City of Guelph, ON created the Dining District (DD) in its downtown. This pilot project closed an intersection to allow restaurants to extend their patios onto the streets, while adhering to social distancing guidelines. The goal of this research is to develop an adaptive and flexible design strategy, as guidance for an improved DD. The methods include a comparison of other municipalities, semi-structured interviews with key informants, and an analysis of street design guidelines. Results were utilized to create a design guidance that outlines design requirements and management strategies for flexible outdoor dining spaces. This research contributes to flexible design knowledge in response to the current pandemic, and to improved downtown streetscapes into the future.