In all honesty, this is a term that I was unfamiliar with until earlier today… and no, it has nothing to do with drugs. A legend trip (or ostension) is a journey made, most usually by a small group of adolescents, to a site of alleged legendary significance. Basically, it’s a journey to a place of legend.
So what constitutes a “place of legend”? This is a location in which some tragic or horrific event (supposedly) occurred where the possibility of a supernatural event or haunting is reputed to occur. The thrill behind the legend being that it places you in a position where you might see or hear something unique, and through visiting that place of legend you become witness to that event and your story is added to the legend. In adolescent circles you might then gain some notoriety among friends… of course, that’s not always the case but it is the idea behind the journey—It’s a rite of passage among adolescents.
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The Witching Hour 