Shoulder rumble strips (SRS) are a proven safety countermeasure that reduce motor vehicle lane departures; however, they may be seen as an impediment to bicycle travel as they decrease comfort for bicyclists and can impact one’s control while bicycling. Existing literature provides recommendations for the placement of regular gaps in SRS, but the testing was limited to low and moderate bicycle speeds. Roads with SRS along long, steep grades present a unique set of risks for cyclists due to the capacity for higher bicycle speeds. This study evaluates how variations in SRS gap lengths and shoulder widths affect a bicyclist’s ability to maneuver through these gaps when riding at higher than average bicycling speeds. The findings suggest that as gap length increases, bicyclist comfort is maintained while downhill speed also increases, with subjects reporting fewer instances of discomfort as the gap size increased. The likelihood of a bicyclist hitting a rumble strip while crossing a gap decreased modestly as the gap size increased. Shoulder width did not appear to significantly influence a bicyclist’s capability of maneuvering across different gap lengths and had only a minor effect on bicyclist speeds.