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Man, I really needed this when I was studying OE. I was trying to do the Alice in Wonderland book and an Oxford textbook but it was really a lot of work compared to other language learning (even compared to Latin). This would have made it a lot more fun.
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The link above mentions Ørberg who did something similar for Latin (Lingua Latina Per Se Illustrata, ebook and audiobook), which I've read through with good success. It's known as the immersive Ørberg method after him.
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The Ørberg method is great, I wish more languages had media utilizing it.
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co-sign this. Oswald the Bear is an amazing book and taught me how to read Old English remarkably quickly.

The first chapter is like a book for toddlers in Old English (with questions and loads of repeated vocab), and each chapter gets a bit harder. Half way in its like a Young Adults Novel level of difficulty. But each step up is relatively small.

The actual story is great too. Æthelstān Mūs is my spirit animal.

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