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I was surprised by how much I loved the last book in the series, Rilla of Ingleside. This book focuses not on Anne, but onto Anne's youngest daughter Rilla. It takes place during World War I and has a more serious tone than the early books. Maybe this is just me, but I know so little about WWI that I had to look up many of the references in this book - this could have been annoying, but I enjoyed getting the history lesson. (Per Wikipedia, Rilla of Ingleside is "the only Canadian novel written from a women's perspective about the First World War by a contemporary.")
There's something else that I realized for the first time on this go-round through these books: the chronological order is not the same as the published order. For example, Rilla of Ingleside was published sixth, but is the last/eighth book chronologically. Normally I am a firm believer in reading books in publication order (see Chronicles of Narnia, etc) but I liked reading these chronologically. It was like getting to watch kids grow up. There were some odd moments by reading them this way. For example, the love letters between Anne and her beau (my lame attempt to not spoil something that everyone in the world knows anyway) were published in the (mostly-epistolary) Anne of Windy Poplars. Chronologically, this book is fourth in the series, but it was the seventh book published. Those love letters are referenced in Anne's House of Dreams (book 5) in such a way, I think, to make them sound private, which was weird since I had just read them. But that is a pretty minor point. What do you think? Should you read these books in published or chronological order?
Find books by L.M. Montgomery on Project Gutenberg or Amazon.