This dissertation research project explored physically disabled skateboarders’ and wheelchair motocross (WCMX) riders’ experiences within the skateboarding (sub)culture. Using (digital) qualitative methods, this project examined 30 physically disabled riders’ experiences within three different “skate spaces” 1) the skateboarding (sub)culture, 2) the digital space of Instagram, and 3) material spaces (skateparks and the streets). Situating this work in Critical Disability Studies, findings illustrated how participation in adaptive skateboarding and WCMX may offer disabled individuals a range of health benefits including enhanced physical and mental health and a myriad of social benefits including improved self-confidence and independence, expanded social networks, and greater sense of community and belonging. Findings also highlighted how participation in adaptive skateboarding and WCMX may allow disabled riders the opportunity to challenge ableist ideas and assumptions about disability. Despite these benefits, however, findings also illuminated how larger social, cultural, political, economic, and structural forces may influence disabled riders’ participation in different sporting milieus. This study contributes to literature on action sports, disability sport, and the sociology of sport and highlight both the benefits and challenges of participation in adaptive action sports for physically disabled people.