For many, a long-distance hike on the 2,650+ mile Pacific Crest Trail (PCT) is the adventure of a lifetime. The federally designated National Scenic Trail passes through 48 Wilderness Areas in California, Washington, and Oregon on its way from Mexico to Canada. The trail experience on the PCT has been changing rapidly over the last 20 years due to two main factors: a four-fold increase in hikers attempting the whole trail each season; and hikers’ rapid adoption of digital technology like smartphones, GPS, and satellite messengers. Through a literature review and accompanying hiker survey, this study aimed to determine how these two factors have combined to alter the trail experience. Despite increased traffic on the trail, hikers appear to still be able to find ample solitude and a feeling of escape from society, and they reported being more likely to form lasting friendships as part of a “trail family”. However, increased traffic has altered many of the sensitive natural landscapes along the trail, contributed to the retirement of some iconic “trail angels” and led to increased conflict between subcultures within the community. Digital technology usage, particularly the use of smartphones and GPS-capable mapping apps, seems to be linked to decreased feelings of solitude, self-sufficiency, and escape. However, digital devices have helped democratize long-distance hiking by simplifying the logistics of long-distance hikes. Users of the devices also did not report reduced feelings of freedom or challenge from their hikes. Moreover, device users still felt that they were disconnecting with technology when hiking on the trail. Acknowledging both positive and negative effects of the changing trail experience, hikers can make more informed decisions about how to mitigate the negative impacts and maximize the positive impacts on the aspects of the trail experience they care the most about.