This paper shows the effectiveness of advanced bone conduction earphones (BCE) for the people who enjoy outdoor activities with respect to entertainment degree and situational awareness (SA) degree. Experiments were conducted to determine the entertainment degree and the SA degree with objective and subjective perspectives by asking participants to walk on the indoor track and the treadmill in four different listening conditions; listening to music through advanced BCE, kernel type earphones, open type earphones, and no music. According to the results of the test on the indoor track, there was no difference in their walking pace between the conditions. Subjectively, the BCE had the same level of entertainment degree as conventional earphones, and higher SA degree than conventional earphones. Objectively, the SA degree was also higher with BCE than with the conventional earphones. These analyses show wearing advanced BCE can be an option to meet both the entertainment and safety purposes for the people who enjoy outdoor activities.