bootleg trail n. a walking path or track worn into the ground by habitual human passage rather than by design. Editorial Note: During Prohibition, the network of people and places that illegally supplied Americans with alcohol was sometimes referred to as the “bootleg trail” by newspapers. It is possible, but not probable, that the path-related “bootleg trail” was derived from the idea that a bootlegger—someone who manufacturers or sells alcohol illegally—might have an operation hidden in the woods that is reached only by a circuitous path. More likely, however, “bootleg” in “bootleg trail” is used in a way more akin its most common meaning, ‘illegitimate, unconventional, unauthorized.’ Thanks to Eric Buck for his insight into hikers and hiking. (source: Double-Tongued Dictionary)
Further reading
In 1916, a small-town newspaper in Pennsylvania printed a fanciful item about a local gathering with a guest list that included, among others, Miss Ella Vader, Mr. Ray Zor, and other punny names. This is part of a complete episode. Transcript of...
A listener remembers her grandmother’s colorful comment when someone arrived late after getting lost: You went around your elbow to get to your thumb. Lots of similar sayings in English suggest roundabout routes or overcomplicated tasks, including...