As cycling gains popularity as a mode of transportation, the frequency of accidents involving cyclists also rises. This has become a major concern for traffic safety, sustainability, and city planning. Identifying the risk factors that contribute to bicycle road accidents remains a significant challenge. This study aims to figure out which risk factors make some road segments more dangerous for cyclists than others. (2) Methods: This study introduces the use of a bicycle simulator to test different road segments involving thirty-nine participants. The impact of demographics and some risk factors related to infrastructure were analyzed in terms of their influence on the perceived level of risk through pre- and post-surveys. (3) Results: The findings showed that the bicycle facility type affects the perceived level of risk. Shared-use roads were ranked as riskiest, while separated bike lanes were least risky. Bicycle roads with no separated safety barriers had higher risks. Heavy traffic jams increased danger among cyclists. Women gave higher risk ratings than men. The perceived levels of risk were then compared with the previously developed risk index and they correlated well. (4) Conclusions: This confirms that the risk index can reliably evaluate the degree of risk of each road segment.