This paper presents a new, regional-scale application of low-stress bicycle connectivity analysis. While prior network-based analyses have focused on the overall improvement in connectivity that could be achieved by implementing a package of projects from a comprehensive bike plan, the purpose of this project was to wholly evaluate potential improvements in connectivity through individual improvements at the street segment level. Using scripts and database tools, levels of traffic stress were assigned to the road network. Incorporating numerous computational optimization measures, shortest paths were calculated between millions of origin and destination pairs to identify the road segments that could most benefit low-stress connectivity. The resulting ranked list of links providing the greatest connectivity benefit allows planners to more efficiently prioritize locations for further investigation and analysis.