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Hi

A man went down the dirt road. A mile later he cleared the trees and turned onto a gravel street.

What does "clear the trees" mean here?
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To get over or past something safely without touching it.

The plane rose high enough to clear the trees.
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So, could it mean that he was walking through the woods and finally got to the gravel path, or maybe something else?
I was thinking about it a little bit and about the definition you gave me, and it seems to me, he just went past the trees (probably he went past the woods) and then set his foot on the gravel path.

I can't think of anything else.
And you shouldn't because that is what he did indeed.

He went past the trees and finally set his foot on a gravel road leading to his beloved town.
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Thanks Fandorin!