Five is such a great age for reading books! They are young enough to enjoy great short and sweet toddler books (perhaps even being able to read them for themselves!), but they also have attention spans big enough to sit through more complex books.
In some ways this love of a wide range of books makes putting together this year’s list more challenging. We read a lot of books, and five-year-old, notoriously picky, Lily seemed to enjoy nearly all of them, so it’s tougher to pick out favorites. When my kids were tiny, the books that made the lists–2 Year Olds and 3 Year Olds and 4 Year Olds–were the ones we maxed out the library renewals on and read daily (or multiple times a day) for two months at a stretch. But by kindergarten, both kids were willing to try a lot of new books.
For this list, throughout the year, I tried to note if Lily asked me to read a book more than once and made sure to write those down. I think these 40 books will be a big hit with your kids, but also longer book lists might be helpful as well. Some big lists I like are in books like Honey for a Child’s Heart, The Read-Aloud Family, and The Read-Aloud Handbook (7th Edition). For a giant list of resources I talk about more than 20 places to find great books in this post.
Many 5-year-olds are pretty adventurous when it comes to books they will let you read to them if you just begin, while they might remain much pickier for books they choose themselves. The exception to this I found was if there was a lot of text, say more than 400 words spread over two pages with only one picture, Lily was definitely suspicious that the book would not be one she liked, and at times it was hard to get her to give that type of book a chance.
Unless, that is, it was a princess fairytale. Lily loves fairytales. We have so many favorite fairytale stand-alone and illustrated collections that I’m going to make a separate post for those. Also by the end of the year, Lily was starting to read some very fun level 2 and 3 readers (she especially LOVED James Marshall’s Fox books), but I’m working on a separate post for those as well. If you are developing a new habit of reading aloud to your child, or your child seems to find these books too long, then try the books for 3 Year Olds and 4 Year Olds, they are shorter, but 5 year olds love them just as much as the younger kids!
And, just like in years past, the vast majority of our picture book reading happens at the kitchen table while my children very slowly eat their vegetables, which are made more palatable by the seasoning of a great book.
40 books that Lily Loved at Age 5
Ira Says Goodbye by Bernard Waber (also Ira Sleeps Over). Bernard Waber, author of the beloved Lyle Lyle Crocodile books, captures the heights and depths of despair of early elementary school friendship with his Ira books. This is one of the books that most thoroughly captures attention during library read aloud time of my kindergarten through second graders.
The Best-Loved Doll by Rebecca Caudill and illustrated by Elliott Gilbert joining the ranks of well-loved toy books like The Velveteen Rabbit, Toy Story, and Dogger (a favorite British children’s picture book by the wonderful Shirley Hughes).This book is about a beloved doll who looks well-loved and not at all fancy coming to a party with beautiful dolls. It was inspired by a real life party attended by the author’s daughter. There is something about capturing the experience of a child with a beloved stuffy that is so universal.
Miss Rumphius by Barbara Cooney is the life story of Miss Rumphius, her travels, and her lupine flower legacy. It’s hard to think of a more beautiful picture book where the images, the language, and the message all come together to make the world a little more beautiful. It’s tempting to try and read this to younger kids, but it wasn’t until five that my kids were ready to sit through the whole thing.
Will I Have a Friend? by Miriam Cohen and illustrated by Lillian Hoban (first grade series) a beautiful and simple book about starting school and wondering if the child will have a friend. The pictures might reveal that the book is from the 1960s, but the sentiments are just as true today as they were when my parents were starting school.
Anatole by Eve Titus illustrated by Paul Galdone. I love everything about this tiny mouse who is horrified to discover people don’t like mice, and then becomes bound and determined to make an honest living (as a cheese taster). J’adore all the French details and phrases thrown in for good measure. This is a book that Evan’s mother used to read to him when he was five, and it’s just as great today.
The World of Pooh by A.A. Milne illustrated by Ernest H. Shepherd. This is classic Pooh, and by five, most kids are ready for some of the long, quirky, lovely stories of Edward Bear coming down the stairs bump, bump, bump. If your child doesn’t fall in love with Pooh immediately (and I will say that the first few pages where the narrator is talking more to Christopher Robin may be a little off putting, so you can skip to page 5 or) read some Disney Pooh to get them used to the characters and try again. I just have a hard time imagining childhood without a little classic Pooh.
Dinosaur Dinner (With a Slice of Alligator Pie) by Dennis Lee and illustrated by Debbie Tilley. These are fun poems that kids love to hear and parents enjoy reading. They are not “classic” poems about nature, but they use rich language and good poetic structure, and they are of course selected by the indomitable Jack Prelutsky, the king of kid poetry.
Feel the Fog by April Pulley Sayre. This is a beautiful book. It has great photographs. It has beautiful language. It’s about nature. It has science and poetry all mixed up in a wonderful experience. I wish there were a thousand more books just like this.
Now One Foot, Now the Other by Tomie dePaola. Get ready for a tear jerker. This sweet book by the amazing Tomie DePaola is about a grandfather who teaches his grandson to walk, and then a few years later when the grandfather has a stroke, the grandson teaches his Grandfather to walk (and hope) again.
Imaginary Fred by Eoin Colfer and illustrated by Oliver Jeffers. A lovely book about imaginary friends and real ones. This is another one that captured everyone’s attention during library read aloud time. A wonderful, recently published book. 
by Grace Lin. A great traditional tale of why the moon gets smaller and bigger throughout the month. I especially appreciated the starry night illustrations and the rhythm of the book. 
Frederick’s Fables : A Treasury of 16 Favorite Leo Lionni Stories by Leo Lionni. Everyone loves Leo Lionni with his beautiful illustration style and his animal stories. Here’s a great collection of some of the most beloved stories. 
Veronica by Roger Duvoisin (Also Jasmine and Petunia). Veronica is a hippopotamus who wants to be famous, but is unprepared for what a famous urban life will entail.
The Quickest Kid in Clarksville by Pat Zietlow Miller and illustrated by Frank Morrison from the author of one of Lily’s all time favorite books, Sophie’s Squash (and one of our favorite Thanksgiving books Sharing the Bread) comes this tale of Alta and a girl with new, shiny shoes and their hometown heroine Olympic gold medalist Wilma Rudolph. It’s full of rich language and girls running fast: a great combo.
A Baby Sister for Frances by Russell Hoban and illustrated by Lillian Hoban (also A Birthday for Frances) when Frances’ little sister arrives, Frances is feeling a little left out and “runs away” hiding in various spots around the house and over hearing her kind parents discuss how much they miss Frances and all her big girl abilities. A favorite Frances book alongside Bread and Jam for Frances.
Now We are Six by A.A. Milne and illustrated by Ernest H. Shepard (also When We Were Very Young) While it took a few minutes for my children to get over the sad fact that Winnie the Pooh is not really in any of these A.A. Milne poems and rhymes, they appreciated them as poems that Winnie the Pooh would approve of: whimsical, funny, universal and extremely specific, and with phrases that are just fun to roll around in your mouth. 
My Breakfast with Jesus by Tina Cho. A sweet book about how children around the world start their days–breakfast, getting ready for school, and praying to start the day in half a dozen countries. 
Our Animal Friends at Maple Hill Farm by Alice and Martin Provensen. If you need a longer book that will keep a kindergartener engaged for a while, our kids loved the quirky descriptions of the various farm animals at the Maple Hill Farm. Along with The Year At Maple Hill Farm these books help city kids understand the rhythms and members of a farming community.
Matisse’s Garden by Samantha Friedman and illustrated by Cristina Amodeo. A beautiful book both in terms of paper cut out illustrations (in the style of Matisse) and language, describing Matisse creating a wall of color and life beginning with a single paper bird.
What Do You Say Dear? A Book of Manners for All Occasions by Sesyle Joslin and illustrated by Maurice Sendak. Proper manners: please, excuse me, pardon me, have never been quite so funny and fun in the outlandish situations Maruice Sendak brings to life. A delight of a book. 
Miracle Man: The Story of Jesus by John Hendrix. If I didn’t know that this book came out in 2017, I would think it was trying to capture the feeling of the show The Chosen. It’s narrative and beautiful and makes the moments of Jesus’ ministry and passion week come alive. This would be a really great read around Easter, but it’s lovely any time of the year.
Mystery on the Docks by Thacher Hurd. Thacher Hurd books have been a big hit this year with their rich language, their fast-paced stories that have a touch of humor, a bit of danger, and a satisfying ending.
Knuffle Bunny Free by Mo Williams. I will say that Lily loves everything Mo Williams creates, and most of it I find exceedingly silly and honestly not my favorite thing to read aloud. (But I think he’s brilliant and writes books that make kids fall in love with reading!) So usually I let Lily read all things Elephant and Piggie or Dont’ Let the Pigeon herself. But I adore the Knuffle Bunny books. Perhaps because I do love books about lost and found beloved stuffed animals (like Shirley Hughes’ Dogger or The Best-Loved Doll by Rebecca Caudill from earlier in this list), but I do not mind reading Knuffle Bunny books over and over, and this third installment is particularly great. (Plus Evan has cousins in Holland, so that’s a fun connection.)
Imogene’s Antlers by David Small. This book has so much charm following the strange day of Imogene when she woke up with antlers upon her head and everyone had an opinion and a reaction to them. I love David Small’s art and this is one of his most charming books. 
Read-Aloud Rhymes for the Very Young selected by Jack Prelutksy and illustrated by Marc Brown. When Jack Prelutsy picks the rhymes you know they are going to be silly and funny and sneak in quality poetry forms and rich language into your kids’ hearts and brains without them even knowing it. And when Marc Brown, creator of the Arthur books, illustrates it–well, what could be better?
Is a Blue Whale the Biggest Thing There Is? by Robert E. Wells. These science were such a great find this year. Robert E. Wells now joins the ranks of our favorite science picture book authors like Gail Gibbons, Joanna Cole, David A. Alder and Jason Chin. Full of great illustrations, fun facts, and generally helping us to understand just how big things can get! Or how small in the also wonderful And What is Smaller than a Pygmy Shrew?)
100 Mighty Dragons All Named Broccoli by David LaRochelle and illustrated by Lian Cho. This is an extremely silly, wonderful book that has kids subtracting from 100 with very humorously named dragons. I found as a read aloud that the kids were so eager to try and do the math in their heads before I turned the pages, but even if they couldn’t get the right answer, they still thought this book was tons of fun. I also read it to first and second graders, and they loved it as well. 
by Laura Geringer and illustrated by Arnold Lobel. This is such a sweet book about two quirky hat loving people who come together, perfectly illustrated by the amazing Arnold Lobel. It’s been charming people since it was on Reading Rainbow in the mid 1980s.
The Cat, the Dog, Little Red, The Exploding Eggs, the Wolf, and Grandma by Diane and Christyan Fox. A funny retelling of, or more the cat attempts to retell, Little Red Riding Hood but dog keeps interrupting with such pressing questions as, if Little Red has a cape, what are her super powers? This was a much requested book at our house for the weeks it was checked out from the library. 
How to Apologize by David LaRochelle and illustrated by Mike Wohnoutka. I keep hoping that books that directly teach emotional regulation and social skills will be enjoyable (and more important instructive!) but they often have not been. So I was so pleasantly surprised by how many times Lily requested How to Apologize. The illustrations are funny and the text is sensitive and thoughtful. I wish this author-illustrator team would do some more!
Wordy Birdy by Tammi Sauer and illustrated by Dave Mottram. This book has a lot of words and the pacing of it makes you want to read it aloud fast, but even if you trip over a few words here or there, the spirit of this too talkative bird who is heading straight for trouble as your child and wordy birdy’s friends try to warn her, is delightful. A favorite at library read aloud time. 
Snatchabook by Helen Docherty and illustrated by Thomas Docherty. The beginning of the story was one of my very favorites: it has beautiful language and an ode to books! I thought the ending fell a little flat, but Lily loved the whole thing. The Storybook Knight by the same team was very similar and also greatly enjoyed.
Humphrey The Lost Whale: A True Story. by Wendy Tokua and Richard Hall illustrated by Hanako Wakiyama. A true story, with photographs at the end, of a whale that swam too far up a river in the San Francisco Bay. This was a big hit for read aloud library time this year from 5k through 3rd grade.
by Mara Bergman and illustrations by Nick Maland. This is a simple story, and likely if we had discovered it earlier it would have made it on to one of Lily’s favorite books lists at age 3 or 4. But still at 5, the tension of the alligator coming towards the kids and getting closer and closer and then the kids turning the tables and frightening the alligator made it a much requested book during Lily’s kindergarten year. A great one if you need something quick and snappy! 😉
Salt in His Shoes: Michael Jordan in Pursuit of a Dream by Deloris and Roslyn Jordan and illustrated by Kadir Nelson. Michael Jordan’s mom and sister team up to tell the story of the young basketball star’s longing to be taller. Lily hasn’t the slightest idea who Michael Jordan is, but just wanted this book to be read over and over. It reminded me a little of her devotion to another book about longing to be taller: Wait for Me! Said Maggie McGee by Jean Van Leeuwen and Jacqueline Rogers.
Simon and the Better Bone by Corey R. Tabor in the spirit of Kitten’s First Full Moon, this retelling of Aesop’s fable “The Dog and His Reflection,” had my kids laughing and giggling at the silly dog all the way through. The layout of this book is clever, and the ending is warm and fun.
There Might be Lobsters by Carolyn Crimi and illustrated by Laurel Molk. Sukie the small dog has many concerns about her day at the beach, not the least of which is lobsters. She prefers not to do much, but faces her fears when someone she loves needs her. An endearing and humorous book that would be a good jumping off place for talking about when we do something new.
Everything You Need to Build a Tree House by Carter Higgins and illustrated by Emily Hughes. This beautifully illustrated book will make you wistful for all things tree houses. Many different types of trees, eco environment, and cultures are scattered throughout the book. 
McDuff Goes to School by Rosemary Wells and illustrated by Susan Jeffers. McDuff has long been a favorite around here, and of the later additions to the McDuff canon our favorite is this one in which McDuff attends obedience school with his French neighbor. It does have a scattering of French words, which is fun for this French minor, and there is a pronunciation guide in the back as well.
Where the Sidewalk Ends by Shell Silverstein. Really this has been a favorite in our house for several years, although this year Lily really seemed to appreciate much of the humor in these classic zany poems. Some of our favorites are “Hector the Collector,” “Sick”, and “Pancake?”
Other lists of Good Books for Five Year Olds from around the web:
Fordham Institute, K-12ReadingList.com, Read Brightly, MadeleineLindley.com, Mensaforkids.org, AMightyGirl.com, FiveBooks.com, and Five in a Row
Printed books that have great lists: Honey for a Child’s Heart, The Read-Aloud Family, and The Read-Aloud Handbook (7th Edition), Books Children Love: A Guide to the Best Children’s Literature, Lessons for a Lifetime, Wild Things and Castles in the Sky: A Guide to Choosing the Best Books for Children and Give Your Child the World.
Also don’t forget to check out my books lists for 2 Year Olds, 3 Year Olds, and 4 Year Olds. Those are the ages when my kids started liking to hear those books, but nearly all of them are quality enough that kids will enjoy hearing them in kindergarten as well. (The difference likely being that your kindergartener won’t need to hear them 50 times before you return the book to the library like a younger child might.)
What are your favorite picture books to read to kindergarteners?