This review will contain spoilers!
In many sentences:
I knew Olive Kitteridge was a pulitzer prize winner, so I was not surprised that I enjoyed reading the book. I was, however, immediately surprised that the first chapter didn't really focus on Olive. Nor did the second or third. It was such a clever technique - to reveal aspects of the main character, Olive, without actually focusing the story upon her. I have definitely not ever read anything that revealed information about a star character in this way. Needless to say, the most striking and enjoyable aspect of Olive Kitteridge was the structure of the book.
Of course, the structure only worked because the rest of the book was so well written. If Strout weren't able to create a town that felt alive, with realistic characters to populate it, no amount of creative structuring would have helped. The combination of all these elements, however, resulted in a very enjoyable reading experience.
In addition to the structure, I also found the character of Olive to be refreshing. It is not often that a book will present a main protagonist who is as deeply flawed as Olive. She was angry, spiteful, and she even confesses to having hit her own child. In spite of all this, though, I could not help but sympathize for her. It was also interesting to see how this sympathy for Olive was enhanced by the short stories that did not focus on her exclusively. Through them we learned about her as a teacher and a friend, and in a way that felt more honest than if we just saw how people acted and spoke about her when she was actually around.
I was also impressed with Strout's ability to talk about growing old, and losing a loved one. I don't know anything about her as a person, but if she hasn't actually experienced this first hand, then it is extremely impressive that she was able to present it so viscerally. Granted, I haven't experienced these things first hand either, but it made me feel like I had, so that is worthy of praise.
It's not difficult, or surprising, to recommend a pulitzer prize winning novel. So, not unexpectedly, I do. Particularly if you want to read a unique, clever title that presents characters in a refreshing manner.