You probably remember the guppies. Or maybe it’s the paper route. If you grew up anywhere near a public library in the last seventy years, Beverly Cleary’s Klickitat Street is basically burned into your DNA. But if you’re trying to introduce a kid to these classics today—or just indulging in a massive hit of nostalgia—getting the Henry Huggins books in order is actually a bit more nuanced than just grabbing whatever has a dog on the cover.
Beverly Cleary changed everything in 1950. Seriously. Before Henry showed up, most children’s books were about polite little English kids or moralistic lessons that felt like eating dry toast. Then came Henry. He was just a kid. He got into trouble not because he was "bad," but because he was a boy living in the real world where things like jars of fish and stray dogs exist.
The Chronological Journey of Henry and Ribsy
If you want the pure, unfiltered experience of watching Henry grow from a third-grader into a slightly more mature (but still disaster-prone) local legend, you have to follow the publication dates. Cleary wrote these in a very specific sequence that mirrors Henry’s aging process.
Henry Huggins (1950)
This is where it starts. It’s the origin story. Henry is bored. He feels like nothing ever happens to him. Then he finds a skinny, hungry dog at a drugstore and tries to bring him home on a bus. It's chaotic. It’s messy. It’s the moment we meet Ribsy. If you don't start here, you miss the foundational bond that makes the rest of the series work.
Henry and Beezus (1952)
By the second book, Henry is obsessed with getting a bicycle. This is also where Beatrice "Beezus" Quimby becomes a major player. Honestly, Beezus is the MVP of the series because she’s the only one who really understands Henry’s logic. This book introduces the infamous bubble gum incident and the red bicycle that feels like a million dollars to a kid in the fifties.
Henry and Ribsy (1954)
Henry’s dad makes a deal: if Henry can keep Ribsy out of trouble for a full year, he can go salmon fishing. Spoilers: Ribsy makes this very difficult. This is peak Cleary humor. It’s also where we see the neighborhood dynamics really solidify.
Henry and the Paper Route (1957)
Henry is finally old enough (he thinks) for a job. He wants a paper route. But he’s ten, and there’s competition. This book captures that specific childhood desperation for independence and "manhood" that feels universal, even if kids today are delivering virtual goods instead of physical newspapers.
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Henry and the Clubhouse (1962)
This one gets a little more "boy-centric," as Henry and his friends build a private space. But of course, Ramona Quimby—who was slowly becoming a breakout star in her own right—decides she isn't having any of that "no girls allowed" nonsense. It's a great look at the friction between the older kids and the annoying younger siblings.
Ribsy (1964)
The final book in the primary Henry arc actually shifts the perspective. It’s essentially a "homeward bound" story. Ribsy gets lost in a shopping center parking lot and has to find his way back to Klickitat Street. It’s surprisingly emotional and serves as a perfect capstone to the series.
Why the Order Actually Matters for Modern Readers
You might think you can just jump in anywhere. You can, technically. Cleary was a master of the episodic chapter. But reading the Henry Huggins books in order allows you to see the subtle shift in the American landscape.
Think about it.
The first book was published just five years after World War II ended. By the time Ribsy came out in '64, the world was a vastly different place. Yet, Henry stays remarkably consistent. He’s the anchor. He represents a childhood that is safe but never boring.
If you skip around, you might miss the way Ramona Quimby evolves. In the early Henry books, she’s just a "pest." She’s a background noise machine in bunny ears. But as the series progresses, you can see Cleary falling in love with Ramona’s character, eventually leading to the massive spin-off series that (let’s be honest) eventually overshadowed Henry himself. But Henry was the pioneer. Without his guppy-breeding mishaps, we never get Ramona’s tricycle adventures.
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The "Secret" Seventh Book?
Wait. There’s a bit of a trick here. While there are six books focused on Henry, he pops up constantly in the Ramona books. If you’re a completionist, you can’t just stop at Ribsy.
Beezus and Ramona (1955) is technically a Ramona book, but Henry is a massive part of it. It fits right between Henry and Ribsy and Henry and the Paper Route. If you want the full Klickitat Street cinematic universe, you have to weave that one in. It gives you the perspective of the girls, which makes Henry’s "boyishness" in his own books even funnier.
Factual Nuances: Portland and the Real Klickitat Street
One thing people often get wrong is thinking Klickitat Street is a fictional creation like Harry Potter’s Privet Drive. It’s not. It’s a real place in Northeast Portland, Oregon.
Beverly Cleary grew up there. She went to the local schools. When she wrote about the Grant Park neighborhood, she was drawing from her own backyard. Today, if you visit Portland, there are actually bronze statues of Henry, Ribsy, and Ramona in the Beverly Cleary Sculpture Garden for Children.
Seeing the physical reality of the setting adds a layer of weight to the books. These weren't fantasies. They were observations. When Henry is struggling with the rain or trying to navigate the hills of Portland on a bike, that was the lived reality of kids in the Pacific Northwest.
The Timelessness of a Kid and His Dog
Why do we still care about the Henry Huggins books in order in 2026?
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It’s because Henry’s problems are internal. Sure, the tech has changed. A kid today might not be as obsessed with breeding guppies to make a few cents, but they definitely know what it feels like to want something (like a bike or a console) so badly it hurts. They know what it’s like to have a pet that is your best friend but also a total disaster.
Cleary didn't talk down to kids. She didn't use big, flowery metaphors. She used small, precise details. The sound of a dog's collar jingling. The smell of wet wool. The specific frustration of having your younger sister's friend ruin your stuff.
How to Get Started with the Series Today
If you’re handing these to a young reader, don’t make it a chore. Don’t force the order if they happen to pick up Henry and the Paper Route first. But, if you have the choice, start with the 1950 original.
Actionable Steps for the Ultimate Reading Experience
- Find the Louis Darling Illustrations: While the newer covers by illustrators like Tracy Dockray are great, there is something magical about the original Louis Darling sketches. They capture the 1950s aesthetic perfectly and help ground the story in its era.
- Read Aloud: These books were designed for the "middle grade" set, but they are legendary read-alouds. The humor in Henry and Ribsy regarding the salmon fishing trip is genuinely funny for adults too.
- Map the Neighborhood: If you’re reading with a kid, look up Klickitat Street on Google Maps. It’s a fun exercise to see the real turns and corners Henry would have taken on his paper route.
- The Audiobook Route: If you have a reluctant reader, look for the versions narrated by Neil Patrick Harris. He captures Henry’s earnestness and the frantic energy of the Quimby household in a way that breathes new life into the text.
The Henry Huggins series remains the gold standard for realistic children's fiction. It’s about the small victories. It’s about a world where a lost dog is the biggest tragedy and a new bicycle is the greatest triumph. By following the Henry Huggins books in order, you get to experience the slow, steady growth of a character who feels less like a literary figure and more like a kid you used to know from down the block.
Start with the bus ride in 1950. Watch the paper route unfold. End with Ribsy finding his way home. It’s a journey that hasn't lost an ounce of its charm in seventy-five years.