Many Canadian manual wheelchair users face many challenges in winter months such as slippage on ice- or snow-covered ramps, snow windrows, and casters becoming stuck in deep or hard packed snow. These barriers impact wheelchair users’ ability to participate in the community. This study aimed to evaluate the validity and feasibility of a winter wheelchair obstacle course known as the Standardized Navigation Of Winter Mobility & Accessibility Network (SNOWMAN). The results demonstrated that the SNOWMAN course authentically represented real-world winter conditions, as confirmed by participant responses and qualitative feedback from four manual wheelchair users. The course was comprehensive, covering a range of winter obstacles typically encountered by wheelchair users. Construct validity was established by differentiating performance between manual wheelchairs and a motorized platform with snow tracks, showcasing varying completion times and device satisfaction levels. Feasibility was also assessed, with the administration protocol being mostly adhered to, safety measures implemented, and usability scores meeting acceptable thresholds. The SNOWMAN course showed promise for evaluating wheelchair adaptations and devices for winter conditions, as well as training users in winter mobility skills. Future research directions include comparing different wheeled mobility devices, exploring adaptations for usability in winter, and developing new technology tailored for challenging terrains and winter conditions. The SNOWMAN course could serve as a valuable tool for both research and clinical applications in enhancing winter mobility for wheelchair users.