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Favorite Childhood Books You Should Totally Read Again

At its core, this is a story about a beautiful friendship between two fifth grade kids who seemed so real that my ten-year-old self could hardly believe Jess and Leslie existed only on the page. I found myself wishing I had my own magical kingdom in the woods I could escape to, and I bawled my eyes out at the end. A moving, multi-layered story about the beauty of childhood and the searing pain of loss.
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The prolific Cleary wrote simple (and funny) stories that kids love to read. Her characters ring true because Cleary based them on her real-life friends and actual neighbors on Klickitat Street in Portland, a street just a few blocks away from her childhood home. Ramona is her best-loved character: I read every book about her, many times. Ramona the Pest is a wonderful place to start: 5-year-old Ramona heads off to kindergarten, where she learns that kindergarten—and life—are full of misunderstandings.
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I probably wasn't old enough to appreciate this instant classic when I first read it as a child, but that didn't stop me. (Thank goodness.) 10-year-old Milo comes home from school one day to find a tollbooth sitting in his bedroom. Since he doesn’t have anything better to do, he pays the toll and drives through–and embarks on a strange journey into a fanciful world where he encounters all sorts of strange characters. A satisfying and delightfully nerdy book that will engage both kids and adults, albeit on different levels.
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A story of a boy and his dogs, and about so much more: love and yearning, struggle and poverty, and hunting—which means it's necessarily about death. My fifth grade teacher made a class of thirty students cry, excepting none, when she read the final chapters aloud. Of note: Rawls spent twenty years writing this novel, then burned it out of embarrassment. Lucky for us, his wife encouraged him to write it again, and he dashed off the whole thing (sans punctuation) in three weeks. Originally published as an adult novel, it still didn't sell until teachers and students got ahold of it.
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The first of many, many mysteries I would come to read in this highly addictive series published under the pseudonym of Carolyn Keene. This is one of the all-time bestselling children's books in English: it's sold nearly 3 million copies. The writing may not hold up on an adult's re-read, but I love the Nancy Drew series anyway: she's smart, she's brave, and she's the one rescuing her boyfriend, instead of the other way around.
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If you come to Montgomery's later, darker series expecting to find a second Anne, you're bound to be disappointed. Luckily, my grade school self had no such preconceived notions. These were the first books that I finished under the covers with a flashlight at 2:00 a.m. because I had to know where Emily's hopes, dreams, and disappointments led her.
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