Pittsburgh’s entertainment district is expanding its infrastructure offerings to promote bicycling and walking to reduce the impacts of traffic. Improving the connectivity and quality of Pittsburgh’s existing pathways is promoting commuting, dining, shopping, and other bicycling activity while reducing single occupancy vehicle trips. Stakeholder charrettes and urban analyses for this project enabled the balancing of the various transportation needs of the Penn Avenue corridor. Landis Evans + Partners, formerly Sprinkle Consulting, part of the HDR team, developed options for bike facilities, all of which included use and cost analyses with recommendations for the most effective opportunities. Bike facilities on Railroad Street (parallel to Penn Avenue) proved to be the best option to enhance traffic operations and safety, to maintain street parking for customers and employees, and to incorporate the regional network of bike routes.