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)

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