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Dorothy and her party first encountered Wish Way when they had become lost, searching Oz for the Scarecrow, who had become emperor of the Silver Islands. After the party got into some trouble and confusion with all their wishes, Dorothy wished them all to where the Scarecrow was. (The Royal Book of Oz)
Dorothy again found the road on her way back to the Emerald City from a visit to one of the kingdoms of Oz. She accidentally wished herself to America, where she then accidentally wished a Hollywood movie dummy to life, and then wished herself and the dummy back to Oz. (The Lost King of Oz)