Finding information by successively following hyperlinks on web pages is a typical task performed on the web. A number of web users search for specific information and several studies have concluded that following the “information scent” is the fundamental process involved in the behavior. The aim of this study was to investigate the relationship between the strength of the “information scent” and user behavior by applying a usability inspection method developed for web usability studies. Three typical usability problems of navigation, (a) a page with a weak scent correct link problem, (b) a page with an unfamiliar correct link problem, and (c) a page with a competing links nested under competing headings problem, were compared with a problem-free page. In this study, we applied the Cognitive Walkthrough for the Web method to simulate a website, and analyze user behavior along with usability problems. Participants were asked to find an article on a simulated encyclopedia website. The success rate, total clicks, total time, fixation count and gaze time were analyzed. The results showed that the critical issues caused by usability problems appear on the target-link page. The results of this study confirm the effect of “information scent” and provide a scientific insight into web navigation.