At the request of the Montgomery County Department of Parks, eight county recreation trails were visualized via 360° photos and video, to help develop a state-of-the-art bike stress index tailored toward mountain bike trails. Using the Google Street View platform to publish photos online as well as several GIS open-source datasets and analytic tools, approximately 60 miles of trail were successfully visualized, and four mountain biking trails were stress-indexed. With the images and stress analysis methodology in hand, the department has the opportunity to lead the nation in visualizing recreation trails by integrating the data products into their online trail web-map. The project deliverables also provide a resource for trail planners and managers who strive to convey variable trail conditions to new and local trail users from anywhere in the world.