10 Heartwarming Books from Your School Days You Should Revisit with Your Grandkids

By: Abbie Crank

Most bookworms can remember the moment they fell in love with reading. Maybe your mother encouraged your love of reading. Or maybe a teacher brought stories and characters alive in a way that made you want to read every book you could get your hands on. Certain books are a literary rite of passage—required reading for bookworms everywhere. If you were an avid reader in your school days, we guarantee you’ve probably read a few of the books on our list. Here are 10 heartwarming ones worth revisiting with your grandkids today.

Anne of Green Gables by Lucy Maud Montgomery 

In 1905, Lucy Maud Montgomery probably would’ve laughed if someone said Anne of Green Gables would be a beloved book in the future, especially since every single publisher she approached had rejected it. For two long years, it sat untouched in a hat box until the author gathered the strength to send it out again. This time, it was accepted, selling 19,000 copies in its first five months. Set in the 19th century, this book tells the story of Anne Shirley, a redheaded orphan sent to live with the middle-aged Cuthbert siblings. Spirited and imaginative, she quickly falls in love with the island of Green Gables and its residents. This is truly one of the most delightful coming-of-age stories ever written with a protagonist that Mark Twain described as “the dearest, most lovable child since the immortal Alice [In Wonderland.]” If you haven’t read it since your school days, do yourself a favor and get your hands on a copy. You won’t regret spending a second with the charming Anne with an E. 

Beezus and Ramona by Beverly Cleary

Technically, Ramona Quimby wasn’t supposed to exist. While writing 1950’s Henry Huggins, Beverly Cleary realized that all her characters were only children and remedied the situation by giving Henry’s friend Beezus a younger sister. She christened her Ramona after overhearing a neighbor call to someone with the same. Little did Cleary know that Ramona Quimby would become the most iconic and memorable character she’d ever written. Ramona’s wild imagination and penchant for chaos perturb Beezus, who struggles to love—let alone, like—her mischievous sister. Adult readers can still enjoy the story and perhaps even recall memories of when they were still a precocious four-year-old. Cleary certainly drew on her own childhood experiences when writing Ramona, admitting in 1995 that she was “very much like Ramona when I lived on the farm and was wild and free.” 

Betsy-Tacy by Maud Hart Lovelace

“It was difficult, later, to think of a time when Betsy and Tacy had not been friends.” This simple line sets the tone for this charming, semi-autobiographical book, part of a ten-book series. Written by Maud Hart Lovelace, Betsy-Tacy takes place in Deep Valley, a fictionalized version of her hometown, Mankato, Minnesota. The first book details how Betsy (based on Maud) meets Tacy, modeled after her bashful, ginger-haired best friend, Frances “Bick” Kenney. Fans of the series know this book is brimming with charm, friendship, and lovable characters. Betsy and Tacy play paper dolls, transform a piano box into a playhouse, and pretend to fly away on a cloud at a picnic. Toward the end, readers meet a character who becomes especially important in the next book. Whether you devoured the series in grade school or have never heard of it until this very moment, it’s not too late to give Betsy-Tacy a chance. In fact, Meg Ryan’s character in the beloved 1998 romcom You’ve Got Mail even recommends the series to a young reader!

Charlotte’s Web by E.B. White

If you read Charlotte’s Web in your school days, then I don’t need to tell you to get some Kleenex ready. After a little girl named Fern saves Wilbur from certain death, the piglet feels indebted to his pint-sized savior. After Wilbur is sold to Fern’s Uncle Homer a month later, he longs for companionship. Enter Charlotte, a barn spider who becomes Wilbur’s second hero. To save him from slaughter, she weaves messages into her web, deeming him “some pig” among other things. The inspiration for Charlotte’s Web came from one of White’s tragic real-life experiences. He desperately tried to save a sickly pig, only for it to pass away in the end. “He had evidently become precious to me,” the heartbroken author later wrote in his essay, Death of a Pig. “That he represented a distant nourishment in a hungry time, but that he had suffered in a suffering world.”

The Lion, the Witch, and the Wardrobe by C.S. Lewis

C.S. Lewis faced numerous challenges while writing The Lion, the Witch, and the Wardrobe in the early 1940s. In fact, he scrapped the first version of the story altogether. “It was, by the unanimous verdict of my friends, so bad that I destroyed it,” he later admitted in a letter. However, Lewis chugged on, writing and refining the story for an entire decade. He floundered a little until “Aslan came bounding into it” and “pulled the whole story together.” The premise of the book is simple. The four Pevensive siblings are whisked away to the English countryside, far from war-ravaged London. Once there, the youngest sister Lucy finds a magical wardrobe that transports her to Narnia, a land straight from a fairy tale. Interestingly, Lucy Pevensive was based on another Lucy—Lucy Barfield, the adopted daughter of his author friend. Lewis even references her in the dedication for The Lion, the Witch, and the Wardrobe, writing: “Some day, you will be old enough to start reading fairytales again. You can then take it down from some upper shelf, dust it, and tell me what you think of it.”

Little House in the Big Woods by Laura Ingalls Wilder

Most of us who’ve seen the TV show probably share an attitude long held by bookworms everywhere: The books are better. Indeed, the first installment in Laura Ingall Wilder’s beloved Little House series is a timeless classic. Based on Wilder’s early childhood memories, Little House in the Big Woods details the lives of Laura, her sisters Mary and Carrie, and her Ma and Pa in their little cabin on the edge of the Wisconsin woods. Pioneer life was difficult, and Wilder doesn’t shy away from the sometimes harsh realities her family sometimes faced. However, their lives were also beautiful, filled with music, trips into town, and an unforgettable Christmas celebration with homemade toys and sweets. This cozy story is the very definition of heartwarming—a must-read for any bookworm, old and young.

The Little Prince by Antoine de Saint-Exupéry

Did you know that The Little Prince is one of the most translated books in history? Originally written in Antoine de Saint-Exupéry’s native French, this novella touches on universal themes of loneliness, loss, and friendship. While Saint-Exupéry lovingly handcrafted the illustrations, the manuscript itself wasn’t in pristine condition when he gave it to his friend Silvia Hamilton. “I’d like to give you something splendid, but this is all I have,” he said before tossing a rumpled bag onto the table and dashing off to France. Inside was the manuscript, marred by scribbles, coffee stains, and cigarette burns. However, a few imperfections couldn’t taint the beauty of this classic tale. The Little Prince has since sold over 200 million copies, becoming one of the best-selling books of all time.

Little Women by Louisa May Alcott 

Louise May Alcott never intended for Little Women to be a smash success. In fact, she never intended to write it at all. Alcott was happily writing Gothic pulp fiction under the pseudonym A.M. Barnard when Thomas Niles, her editor at Roberts Brothers, requested she write a book for girls. Still a tomboy at heart, Alcott struggled to find motivation for the project. “Marmee, Anna, and May all approve my plan. So I plod away, though I don’t enjoy this sort of thing. Never liked girls or knew many, except my sisters; but our queer plays and experiences may prove interesting, though I doubt it,” the author wrote in her journal. Regardless of her feelings, Alcott wrote 402 pages in less than six weeks. It became an instant bestseller, cementing Alcott as one of the most prominent and celebrated authors of the 19th century. Little Women remains popular today and reportedly still sells 1,000 copies a month.

The Secret Garden by Frances Hodgson Burnett

The Secret Garden isn’t the only beloved children’s book Burnett wrote. She’s also the author of A Little Princess, among other celebrated works. However, none were quite so captivating as The Secret Garden. This story features an orphan named Mary Lennox, a Gothic mansion, and a mysterious walled garden. The book’s setting may have been based on Maytham Hall in Kent, England, where Burnett and her husband lived from 1898 to 1907. Burnett did, in fact, uncover an overgrown garden behind an ivy-covered door, just like Mary Lennox. The author quickly threw herself into a full-scale restoration project, establishing an outdoor study and a beautiful rose garden. While little is known about Burnett’s creative process as she wrote The Secret Garden, a letter to her publisher reveals that she considered the book “one of [her] best finds.” This bookworm couldn’t agree more!

Winnie-the-Pooh by A.A. Milne 

The fictional Christopher Robin wouldn’t exist without the real-life Christopher Robin, son of author A.A. Milne. The author’s son invented voices and personalities for his cherished stuffed animals, one of which was a teddy bear he received on his first birthday. Originally named Edward, the bear’s name was changed to Winnie in honor of a Canadian black bear the family often visited at the London Zoo. The second part of the bear’s name, Pooh, might have come from a friend’s pet swan. Set in the idyllic Hundred Acre Wood, these stories follow the adventures of Christopher Robin and his merry band of animal friends. Who can forget when Eeyore loses his tail? Or when Pooh accidentally gets stuck in Rabbit’s door during a visit? Winnie-the-Pooh is a beloved classic for a reason. Sadly, Milne’s later years were marked by unhappiness. Christopher Robin resented his father, and the two rarely saw each other before Milne passed away in 1956. And while he later grew to detest the Winnie-the-Pooh books, they granted the jaded author one of his deepest desires: permanence as a writer.

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