I have been reading chapter books to Preston lately. He really loves them, but it has been difficult to find good ones to read that I know he’ll understand (and I won’t get bored reading). I did a Google search and found this article by Melissa Wiley which I’ve copied and pasted below:
Chapter book suggestions for a four-year-old — Here in the Bonny Glen.
All right, suggestions for a four-year-old who is ready to listen to chapter books:
• My Father’s Dragon series by Ruth Stiles Gannett. Our family’s favorite choice for that first “book with chapters” read-aloud. Scott is working his way through the trilogy with Rilla right now.
• My Naughty Little Sister by Dorothy Edwards.
• Milly-Molly-Mandy by Joyce Lankester Brisley, and its sequel, More Milly-Molly-Mandy. LikeNaughty Little Sister, these are episodic books; each chapter is its own little story. Milly-Molly-Mandy’s busy daily adventures—very much rooted in simple domestic village life, running errands for her family, staying alone for the first time, deciding what to spend her hard-earned pennies on—have enchanted all four of my girls around age four or five.
• Winnie-the-Pooh (does that go without saying?)
• the first two Betsy-Tacy books can be perfect for a five-year-old, but I have found my girls really clicked with Betsy at a slightly older age—perhaps seven or eight.
• Kipling’s Just-So Stories. I began reading these to Rilla at age four and she adores them—the belly laughs are irresistible. I rather suspect, however, that she believes “O Best Beloved” is referring to her specifically and is likely to be disgruntled when she realizes I read those words to her big sisters before her, in their day.
• Ramona the Pest by Beverly Cleary.
• The Boxcar Children by Gertrude Chandler Warner (the very first one, which has a special kind of sweetness and earnestness to it—this was a head-over-heels-in-love book for Jane at age 4).
• Old Mother West Wind and other Thornton Burgess animal stories—now, for us these were hit or miss. I had come kids adore them, and others who found them dull.
• Mr. Popper’s Penguins by Richard Atwater. In our house, this is a read-aloud reserved exclusively for the daddy.
• Pippi Longstocking, of course!
• The Borrowers by Mary Norton, and The Littles by John Peterson. When it comes to tiny people living hidden in human houses, I’m a Borrowers girl all the way. Then again, the Littles have tails.
• Tumtum and Nutmeg by Emily Bearn. Small animals behaving like people: almost as much fun as tiny hidden people. And what’s that other very young mouse-people series I’m forgetting? Hedge something. Brambly Hedge! That’s it.
• I don’t find Johnny Gruelle’s Raggedy Ann Stories very easy to read aloud—he tends toward the insipid—but I remember how magical I found those books as a very young child. Sodapop fountains!
• The Cricket in Times Square. The kind of middle-grade story that always seems to hold our current four-year-old spellbound when Dad is reading it to the older kids.
• The Stories Julian Tells by Ann Cameron. There’s a sequel, too—More Stories Julian Tells. I love these books! Need to pull them out for Rilla and Wonderboy.
This list could go on for a really long time. I know there are many great books I’m omitting, but these are the ones that come most immediately to mind. HOWEVER, it is almost guaranteed that as soon as I publish this post, I will kick myself for forgetting some particular favorite. Like actually just this minute I have remembered Doctor Boox. I adore Doctor Boox. I must go and find our copy of Doctor Boox immediately. Immediately!
I have a whole nother batch of suggestions for a six- or seven-year-old. For a four-year-old, I’ve seen the most connection and delight with very simple, homey kinds of books. That’s why I haven’t included authors like C.S. Lewis, Roald Dahl, Kate di Camillo, E. Nesbit, Edward Eager, E. B. White, Dorothy Canfield Fisher, and Frances Hodgson Burnett—I save those for a few years down the road. (Having said that, James and the Giant Peach might be a great fit for a four-year-old. Humongous bugs! What could be better?)
For a four-year-old, I would also reiterate my enthusiastic recommendation of Jim Weiss and Jay O’Callahan story tapes.
And folk and fairy tales by the dozens.
And I’ll add this thought—although Rilla (who turned five in April) has indeed enjoyed several of the chapter books I’ve mentioned above, and her My Father’s Dragon time with Daddy is her favorite part of the day, she would rather read picture books with me than a “Long Book” at this point. Almost every day she goes around the house collecting a stack of picture books for “quiet reading time.” (By that she means being alone with me—it isn’t actually all that quiet.) 
I haven’t added to the Rillabook list in the sidebar for weeks because lately all her choices are books we’ve read and read and read again. I find this to be very common at the emergent reader stage—as opposed to, say, a ten-year-old who seems to want new new new more more more at a rate nearly impossible to keep up with.
(I think these cycles of rereading beloved favorites and hungering for exciting new frontiers continue all through life. In my early teens, I was a binge rereader—both of my childhood favorites and of newer passions like the Pern books or—dare I admit it—the unflinchingly formulaic Silhouette First Love romances of the ’80s, for which I actually had a subscription. It makes sense that in times of great change or stress, formula fiction and the deeply familiar offer special comfort and appeal. This is probably the same psychological need that makes me crave nothing but Agatha Christie when I’m sick.) ….
Now if you’ll excuse me, I need to go introduce my children to Doctor Boox.
