We present a statistical learning approach for finding recreational trails in aerial images. While the problem of recognizing relatively straight and well defined roadways in digital images has been well studied in the literature, the more difficult problem of extracting trails has received no attention. However, trails and rough roads are less likely to be adequately mapped, and change more rapidly over time. Automated tools for finding trails will be useful to cartographers, recreational users and governments. In addition, the methods developed here are applicable to the more general problem of finding linear structure. Our approach combines local estimates for image pixel trail probabilities with the global constraint that such pixels must link together to form a path. For the local part, we present results using three classification techniques. To construct a global solution (a trail) from these probabilities, we propose a global cost function that includes both global probability and path length. We show that the addition of a length term significantly improves trail finding ability. However, computing the optimal trail becomes intractable as known dynamic programming methods do not apply. Thus we describe a new splitting heuristic based on Dijkstra's algorithm. We then further improve upon the results with a trail sampling scheme. We test our approach on 500 challenging images along the 2500 mile continental divide mountain bike trail, where assumptions prevalent in the road literature are violated.