Trail users that experience acceptable social and ecological conditions are more likely to act as trail stewards, exhibit proper trail etiquette, and use low-impact practices. However, the relationships between specific trail conditions and experiential elements of long-distance hiking are not well understood. Therefore, the purpose of this study was to identify how trail conditions influence particular elements of the long-distance hiking experience. The researchers used a mixed-methods approach involving semi-structured interviews (n = 17), quantitative questionnaires (n = 336), ecological measurements of trail conditions (n = 21–5 km sections), and modified Recreation Suitability Mapping (RSM) techniques to quantify the relationships between five trail conditions (trail incision, muddiness, rugosity, trail width, and gradient) and four experiential elements of long-distance hiking (level of challenge, perceived impact to musculoskeletal system, valuation of tread aesthetics, and ability to maintain an ideal hiking pace). Quantified values were weighted, analyzed, and mapped using SPSS 22.0 and ArcMap 10.2.2. Significant differences exist in the scores and distributions of ecological measures across all sections, indicating that trail conditions vary significantly across sampled trail sections. Although, long-distance hikers felt all four experiential elements were important, tread aesthetics was ranked by 50.2% of sampled hikers as the most important experiential element to the overall experience. The resulting information after applying the weights suggests what particular type of experience is likely for each trail section considering the presence of trail conditions.