For many years, running-related injuries have been studied on surfaces that are flat, smooth and predictable but there are few studies that have reported on injuries in trail running. Therefore, the purpose of this paper was to report on the prevalence of injuries incurred during trail running, the anatomical location most affected by injury, the type of trails and terrains on which injuries most occurred and the type of footwear associated with trail running injuries. A large sample (n = 1016) responded to an online retrospective questionnaire on trail running injuries, the types of trails and terrains on which they ran and the footwear that they used. The sample was determined to represent a range of ages and geographical regions in the United States. We found that 359 respondents reported a trail running injury with 872 injury occurrences with injuries having different frequencies of occurrence. The most commonly reported injury was a rolled or sprained ankle. A significant association was found between runners that sustained a given injury and their preferred trail and terrain types. A large majority (75%) of trail runners wore running footwear specifically designed for trail running. These results suggest that injuries in trail running are different than observed in road running where traumatic injuries to the ankle are more prevalent in trail running and where chronic injuries to the knee prevail in road running. We also noted that trail running injuries were only marginally the result of the type of trails and terrains on which runners most often ran. We did not find any association between the use of footwear specifically designed for trail running and injury risk.