Running offers a convenient and affordable method of keeping fit and maintaining good cardiovascular health. In this paper, we describe the experiences of a group of runners whose practices are rarely profiled: individuals who identify as legally-blind, some of whom run competitively, while others run for purposes of leisure. We specifically focus on planning strategies undertaken, experiences running both with and without sighted guides, the impact of situational and environmental factors, and the ways in which technology is utilized. The study has revealed a set of insights which if capitalized upon could offer considerable promise to support independent running. These include examining ways to reduce levels of uncertainty faced by runners, supporting autonomy, providing greater levels of environmental awareness, and aiding socialization when running. Findings from the work offer promise to interface designers to improve inclusiveness when developing technologies to support runners.