Backpacker editor Zoe Gates sets off to discover if chatbots are the solution to our trip-planning woes. Preparing for wilderness excursions can be frustrating, even for seasoned adventurers. Tsunamis of online information—conflicting top ten lists, distracting ads, and trip reports of varying quality—can stand between you and getting out the door. Artificial intelligence tools claim to deliver detailed travel itineraries in response to just a single question, but can a robot really design a safe, worthwhile adventure? In an effort to simplify her weekend excursions, Zoe experiments with Outside’s in-development chatbot, Scout—and is totally at the whims of her computer.

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