Why the Anne Shirley series books are still messing with our heads a century later

Red hair. Temper. A penchant for getting drunk on raspberry cordial—accidentally, of course.

If you grew up with the Anne Shirley series books, you know exactly what I’m talking about. Lucy Maud Montgomery didn't just write a story about an orphan in Prince Edward Island. She basically created the blueprint for every "quirky" female protagonist that followed for the next hundred years. But honestly, if you haven't revisited the series since you were ten, you're missing the weirdest, most beautiful, and occasionally most frustrating parts of the saga.

It’s not just about a girl with a big imagination. It’s about grief, the brutal reality of aging, and how a tiny island in Canada became the center of the literary universe.

The real order of the Anne Shirley series books (it’s not what you think)

Most people stop after Anne of Green Gables. They think, "Okay, she got the house, she kept her hair, she stayed with Marilla. The end."

Nope. Not even close.

Montgomery actually wrote these books out of order. She published the first one in 1908, and it was a massive, overnight success. We’re talking Mark Twain sending her fan mail kind of success. But because she was tied into a pretty restrictive contract with her publisher, L.C. Page, she ended up writing some of the later books much later in her life. For instance, Anne of Windy Poplars (which covers her years as a principal) and Anne of Ingleside were written decades after the original books, filling in gaps that readers were screaming for.

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If you want to read them chronologically by Anne's life, here is how they actually fall:

1. Anne of Green Gables (The childhood years)
2. Anne of Avonlea (The "I'm a teacher now but still making mistakes" years)
3. Anne of the Island (College in Kingsport—this is where the romance gets real)
4. Anne of Windy Poplars (Letters to Gilbert while she’s a principal)
5. Anne's House of Dreams (The early marriage years, and honestly, the darkest book)
6. Anne of Ingleside (Anne as a mother)
7. Rainbow Valley (Mostly about her kids)
8. Rilla of Ingleside (The WWI book)

There is also The Blythes Are Quoted, which was Montgomery’s final work. It’s gritty. It’s experimental. It was actually delivered to her publisher on the day she died in 1942. It wasn't published in its full, unedited form until 2009 because the original editors thought it was too dark and cynical for the "Anne" brand.

The Gilbert Blythe factor

Let’s talk about Gilbert. Everyone has a crush on Gilbert Blythe. It’s a universal law. But in the Anne Shirley series books, his pursuit of Anne is a masterclass in the "slow burn." He waits years. He survives her hitting him over the head with a slate. He gives up a teaching post so she can stay close to home.

The brilliance of their relationship isn't that he's perfect. It's that he treats her as an intellectual equal in a time when that wasn't exactly the norm. When they finally get together in Anne of the Island, it isn't some fairy tale ending. It’s the start of a partnership that survives some pretty heavy-duty trauma.

Why Anne's House of Dreams is the secret MVP

If you only read the first three books, you’re getting the "PG" version of Anne. Anne's House of Dreams is where Montgomery starts taking the gloves off.

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Anne moves to Four Winds Harbor. She’s a bride. She’s happy. Then, she loses her first child, Joyce.

It’s heartbreaking. It’s also one of the few times in early 20th-century literature where the physical and emotional toll of neonatal loss is described with such raw honesty. Montgomery herself lost a son, Hugh, at birth, and you can feel that real-world grief bleeding onto the page. This book introduces characters like Miss Cornelia, who hates men, and Captain Jim, who tells stories of the sea. It moves the series away from "schoolgirl antics" and into the realm of a serious adult novel.

Honestly? It's the best one.

The Prince Edward Island effect

You can't talk about the Anne Shirley series books without talking about the setting. Cavendish, PEI (the real-life inspiration for Avonlea) is basically a pilgrimage site now.

Montgomery described the red mud and the blooming orchards so vividly that people still travel from Japan, Poland, and the UK just to see if the light really hits the water that way. Spoiler: it does. But there’s a nuance here. Montgomery used the landscape as a reflection of Anne’s internal state. When Anne is stifled, the landscape feels small. When she’s growing, the horizon expands.

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It’s a literary technique called "pathetic fallacy," but Montgomery makes it feel less like a trope and more like a character. The trees aren't just trees; they’re "The Snow Queen" or "The Haunted Woods."

The "Anne" variations and misconceptions

People get confused because there are so many adaptations. You’ve got the 1985 Megan Follows miniseries (the gold standard for most), the 1934 film, and the more recent Anne with an E on Netflix.

A lot of purists hated Anne with an E because it added "darkness" that wasn't explicitly in the text. But if you read the later Anne Shirley series books, that darkness was always there. Montgomery struggled with depression. Her journals are full of it. The books were her way of fighting back against a world that she often found cold and unforgiving. She chose to write about "kindred spirits" because she was desperately looking for them in her own life.

Getting started (or restarted) with the series

If you’re looking to dive back in, don't just buy the cheapest ebook version you find. A lot of the public domain versions are missing chapters or have terrible formatting that ruins Montgomery's specific cadence.

Look for the Oxford University Press editions or the Penguin Classics. They usually have the best notes on the Scottish and Canadian idioms Montgomery used. You’ll also want to look for the "unrestored" versions of Anne of Windy Poplars, as some editions cut out the more eccentric side-plots.

Actionable Next Steps:

• Read chronologically, not by publication date. Start with Green Gables and go straight through to Rilla of Ingleside. Skipping the "middle" books like Windy Poplars makes the transition from college student to mother feel jarring.
• Track the "Kindred Spirits." Pay attention to which characters Anne labels as such. It’s Montgomery’s way of Categorizing empathy and emotional intelligence.
• Research the author's life. Understanding Lucy Maud Montgomery’s legal battles with her publishers and her difficult marriage to a minister adds a layer of "reading between the lines" that makes the books much more complex.
• Visit the L.M. Montgomery Institute website. They host academic papers and historical context that explain the real-world events (like the suffrage movement and the transition to the automobile) that happen in the background of the later books.

The Anne Shirley series books aren't just for kids. They’re a record of a woman trying to maintain her imagination in a world that keeps trying to turn her into a "sensible" adult. That’s a struggle that hasn't aged a day.