The Best Classic Chapter Books to Read Aloud to the Littlest Listeners

Your children love picture books! Great job Mom!

You’ve started them on the path to a lifelong love of reading! Now for that tricky transition to chapter books. You’re longing to share The Hobbit, Narnia, and Anne of Green Gables with your five year old (or your three or four year old if he or she has a long attention span), but WAIT!

First chapter books are an important and memorable experience for your preschooler or kindergartener!

And believe me, the transition to chapter books will be much smoother if you begin with one of these delightful books written just for children listening to their first chapter books. These classic first chapter books have charming illustrations scattered throughout and short chapters the perfect length for a limited attention span.

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Milly-Molly-Mandy is a sweet little girl enjoying family and small town life in a multi-generational home. Nostalgic and innocent stories with lots and lots of illustrations!

Jenny is a fashion-loving little black cat who longs for some friends. In Jenny and the Cat Club, she meets a memorable group of beautiful and ragged felines. A book about making friends, finding your own talents, and appreciating others’ differences. There are several more books about Jenny’s adventures available!

Raggedy Ann‘s cheerful nature and simple adventures have delighted children for over 100 years! Always a hit with 4-5 year old girls!

Twig‘s impoverished family lives in a tenement house. But one memorable day, a tomato soup can, a dandelion, and her imagination bring the best kind of magic into her life. After that day, Twig sees her life and neighbors through new eyes.

This is a transformation through imagination story in the tradition of Nesbit and MacDonald, so I personally liked it. But if you are very sensitive to the use of “magic” in stories, you may want to avoid this one.

Of course every child needs to listen to The Complete Tales of Winnie-The-Pooh! This beautiful hardcover edition includes lots of full color illustrations to make this beloved first chapter book even more enjoyable.

The Thornton Burgess 26-Book Set brings you to the world of the little forest animals. Most chapters are only 2-4 pages. Not as many pictures as some of the other books on this list, but still held the attention of my 4 year old.

Happy Little Family focuses on Bonnie, the youngest in an Appalachian family. At 4 years old, Bonnie feels quite grown up and ready to participate in all the family fun. All 4 years old can relate to her little joys and disappointments.

Continue reading Bonnie’s adventures in Schoolhouse in the Woods. Bonnie starts school, learns to read, and makes friends.

If you’re looking for more stories for 4-6 year old listeners, I highly recommend diving deep into fairy tales and folk tales! Check out my list of Good Fairy Tales, Fables, and Tall Tales for Catholic Kids.

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