In recent years research and planning efforts to enhance the conditions and opportunities for active transportation modes have increased significantly; however, these efforts have primarily focused on pedestrians and bicyclists. Skateboarding and other alternative modes of mobility remain an untapped potential for healthy and sustainable travel. This research addresses numerous knowledge gaps in the literature on utilitarian skateboarding under the larger umbrella of active transportation. Analysis of online survey results and semi-structured interviews with skateboarders in Portland, OR provides insight into the motivations and barriers of traveling by skateboard and the demographics and perceptions of skateboard commuters. Like bicyclists and pedestrians, skateboarders value safe, comfortable, and aesthetically pleasing places to travel and are sensitive to surface conditions, distance, and slope. These similarities present a unique opportunity for cities to create facilities that accommodate diverse users. Disaggregating results by the respondents' gender, skill level, and frequency of transportation-oriented skateboarding highlights significant differences in levels of perceived safety and the practicality of utilitarian skateboarding. The findings have implications for the future of active transportation planning which support Elaine Stratford's vision of "generous geographies that allow for more, and playful, mobilities in the city."