I read The Canterbury Tales in the original Middle English about a year ago. I read an Everyman's Library edition that had helpful notes in the margin as well as footnotes for longer passages that needed explaining. One I got used to it, though, I seldom needed the notes. Having studied German helped a lot because the words that veered furthest from modern English were often recognizable as German. But I think this would be a monumental undertaking for someone who is not a native speaker of English to begin with.
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