Injuries from inline skating have risen sharply in many cities around the world. To understand risk-taking behavior and safety practices associated with urban inline skating, 2,210 outdoor skaters were observed in Boston, Massachusetts. In this study estimated age, gender, use of helmets, wrist guards, elbow and kneepads were recorded. Skaters were coded as beginner, average, or advanced, and skating locations were classified as street, sidewalk, or bicycle path. The result shows that about 60% of skaters wore wrist guards, but only 5.7% wore helmets. Males wore less protective equipment than females, and were more likely to skate on streets. Beginners and advanced skaters wore more protective gear than average skaters. Surprisingly, street skaters wore less protective gear than skaters on sidewalks or paths. The conclusions of this study are that a renewed focus on the importance of wearing helmets is needed. Given the higher injury risks for males, clinicians and public health experts need to target male skaters in prevention efforts. In addition, average and advanced skaters need to be convinced that even though they have improved, it is still important to wear protective gear.