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Trying to remember a book. I read it as a tween in the late 80s. Here’s what I got so far:

  1. A boy has to go on some kind of quest in another dimension (kind of like Narnia in that it was right there, but in a different universe that he got to by some normal way).
  2. He is on the quest for someone else (don’t know who).
  3. He is walking along some road and he can’t leave the road for any reason - if he does he’ll never return
  4. At one point he is assigned a task by people (or creatures) he meets on the way: he must climb a tree and get a fruit for someone, but no matter what he must not eat the fruit and he must not look down or .... something really bad.

That’s what I got. I read it in the late 80s, but it could’ve come out any time post World War II I’d guess.

  • You're describing Orpheus' trip into the underworld – Valorum Dec 22 '18 at 23:46
  • Not sure about the tree bit, the rest is fairly common tropes, but look at Song of Earth and Power, by Greg Bear. I've seen it come up a bit. It's individual novels were first put out in the 80s. – Radhil Dec 23 '18 at 2:12
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Alright - I solved it. I was right on most points. It was The Castle In The Attic by Elizabeth Winthrop.

Some clues that triggered it for me were: (From the Wiki article)

Spoilers below:

Sir Simon is tempted by the apparition of his old horse Moonlight, leaves the path and disappears, after having warned William that doing just that will cause one to get lost forever.

And

William manages to make it through the forest on his own and encounters an old man at an apple tree. After getting a specific apple for him, the old man reverts into a young man and reveals he was under a spell.

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