Trends dating from the 1970s show that males are significantly less likely than females to attend college and to remain in higher education once enrolled. Although this gender imbalance is undisputed, there is little agreement about the causes of the disparity and even less solid research to guide policy. Educators nowadays still wonder why young men underachieve educationally in comparison with women. In this article, the author suggests how it is better to question why college-age men succeed at difficult achievement tasks. One difficult task that the author finds more men are apt to succeed in is hiking the Appalachian Trail. Here, the author examines the features of this experience and explores the factors that motivate men to succeed in this challenge. The author believes that learning the factors that motivate college-age men to undertake hiking in the Appalachian Trail and the conditions that lead to their success hold strong implications for the design of higher education settings that will attract and retain greater numbers of male students than current settings. (Contains 19 notes.)