A few months back, at the start of summer, I argued in favor of reading to your children, even after they’ve moved beyond the early grades and are reading on their own (or craving screen time). This column elicited a plethora of heartwarming and intriguing responses. Given my preference to spend the summer engrossed in actual books rather than education news and impenetrable research reports, I feel inclined to delve into those interactions a bit further. If that interests you, continue reading. If not, no worries—I’ll catch you next week.

One common question arose: What constitutes a good family read? There were entertaining anecdotes about repeated disappointments and cherished books that proved less captivating than parents remembered. I found these experiences relatable.

There are books that I once adored but haven’t withstood the test of time. Whether it’s due to changes in me, my children, or the era, the magic of these stories has faded. I recall being captivated by Daniel Pinkwater’s Lizard Music and Susan Cooper’s Dark Is Rising series as a child, but when we read them together as a family, the enchantment was lacking.

We’ve encountered books that we struggled to finish, like Jules Verne’s Journey to the Center of the Earth, which read like a tedious lecture on Icelandic volcanic formations. On the other hand, there are delightful books, such as A. A. Milne’s Winnie the Pooh tales, that the boys enjoyed in their younger years but have now outgrown.

All of this prompted me to ponder which family reads are likely to resonate. For what it’s worth, I’ve identified four principles that seem effective for us.

Firstly, I appreciate books that stimulate questions and discussions with their complexity. It’s a positive sign if I sense that my role as the reader is essential, where they would struggle without my guidance in rephrasing and addressing queries. While I’m not seeking Tolstoy, I do seek material that nudges them beyond their comfort zone.

Secondly, I find it beneficial if a book is slightly overwritten, provided the plot is clear and the characters are compelling. I’m willing to simplify and modernize as needed—trimming excessive scene descriptions, adjusting language, and the like. This exposes them to engaging narratives they may not otherwise pick up.

Thirdly, a touch of intrigue, oddity, or misbehavior enhances our reading experiences. These elements spark lively conversations, elicit amusing reflections at breakfast or bedtime, and sustain their curiosity about what comes next.

Lastly, I prefer having a personal connection to the book. Approaching it with prior fondness makes our shared reading experience more meaningful. I relish introducing them to nostalgic favorites that I believe they’ll appreciate and wouldn’t stumble upon independently.

Recently, several correspondents inquired about recommendations beyond the familiar classics like the Narnia series, James and the Giant Peach, The Phantom Tollbooth, or Harry Potter

Here are five vintage books I wholeheartedly endorse. In keeping with the theme of “Old School,” all of them are at least four decades old. And so it goes.

The Wonderful Story of Henry Sugar. Roald Dahl’s novella tells the tale of a privileged idler who stumbles upon a transformative book and evolves into a mystical Robin Hood. It’s a peculiar narrative laden with British slang, enigmatic abilities, gambling, and a backdrop rooted in early 20th-century India. While I translated much of the language and pruned certain sections, the children were intrigued and bombarded me with questions about blackjack, orphanages, meditation, and more.

The Westing Game. Ellen Raskin’s ingenious, briskly paced, intricate narrative revolves around a diverse group of potential heirs vying for a fortune by deciphering the rules of a cryptic game. Replete with memorable characters, puzzling riddles, and spanning fewer than 200 pages, this book benefits greatly from adult guidance in unraveling the clues, characters, and overall mystery.

The Great Brain. These tales, over half a century old, are situated in 1890s Utah. One might doubt their enduring appeal, but they hold up remarkably well. Narrated by a younger sibling about his scheming, silver-tongued middle brother with a penchant for money and a generous spirit, these stories feel surprisingly relevant. Set in a time when indoor plumbing was a novelty and a penny held real value, this frontier world demands substantial context. The series eventually spawned seven sequels, several of which are equally captivating.

Around the World in Eighty Days. In the late 19th century, stoic Englishman Phileas Fogg recognizes the technological advancements in transportation that could theoretically allow a circumnavigation in 80 days. Wagering half his fortune on accomplishing this feat, Fogg embarks on a journey fraught with humor, twists, camaraderie, and betrayal. I found greater enjoyment reading it aloud with my children than when I read it solo as a kid, primarily because certain travel descriptions were verbose and tedious. The premise is intriguing, but benefits significantly from a reader who can trim the excess and elucidate the peculiarities.

Shoeless Joe. W. P. Kinsella’s unconventional novel is the most unexpected inclusion on this list. I had reservations about the children’s reception, given its verbosity—with copious adjectives and strained similes. However, the narrative proved remarkably engrossing once the excess was pruned. Despite occasional misplaced allusions to sensuality, easily edited out in this otherwise age-appropriate tale, it offers a captivating blend of history spanning the 1919 Black Sox scandal and J. D. Salinger’s lore, interwoven with a poignant story of parenthood, yearning, and baseball. Moreover, this book birthed the iconic Field of Dreams. Quite the bonus.

If you have insights, observations, or additional titles to recommend, don’t hesitate to share. This ongoing dialogue never fails to pique my interest.

Frederick Hess is an executive editor of Education Next and the author of the blog “Old School with Rick Hess.”