Ten Favorite Milestones Picture Books

From losing teeth to losing confidence, there are countless milestone experiences that children face. Reading books can help build emotional resilience as kids better understand such experiences and learn how to handle the potentially difficult milestones they will face. Check out some of our favorite books that tackle childhood milestones!


Here Comes the Tooth Fairy Cat by Deborah Underwood, illustrated by Claudia Rueda

When Cat loses a tooth, the tooth fairy brings him a coin. But he wants to meet the tooth fairy! When he tries to trick her into coming again, she leaves him a note—and a tooth-collecting challenge! Will Cat and his new partner Mouse collect all the teeth—without getting eaten? This fun story is a great way to celebrate losing teeth!


Maple by Lori Nichols 

Just before Maple was born, her parents planted a maple tree. As she grows, the tree grows—but the older she gets, the more she needs a real friend. When her parents plant another tree, Maple learns that she’ll be a big sister—and that sisterhood, combined with special trees, is just what she needs. This story is perfect for big siblings!


On the First Day of Kindergarten by Tish Rabe, illustrated by Laura Hughes

 From riding the bus to sliding down the slide, painting a picture, and going on a field trip, there are so many things to love about kindergarten! This cumulative story is perfect for kids who can’t wait—as well as those who are nervous!—to start going to school. 


Waiting for Baby by Rachel Fuller

Waiting for a baby is exciting—and full of questions! In this book, a little boy asks all kinds of questions as his mother sorts through baby clothes, visits the doctor, and prepares for the new arrival! A perfect read-aloud for expectant parents, this book allows readers to answer new baby questions in a fun and engaging way.


Charlotte and the Rock by Stephen W. Martin, illustrated by Samantha Cotterill

All Charlotte wants is a pet, but her parents’ gift of a pet rock is not what she had in mind. But despite the challenges of caring for a pet rock, Charlotte and her rock eventually become friends. Then, to Charlotte’s surprise, the rock cracks—revealing a surprising new pet! Complete with Charlotte’s rules for caring for a pet rock (which can be applied to any pet!), this story is a fun read-aloud—great for any child with a new pet!


Hello, New House by Jane Smith

In this simple picture book, a young girl leaves her old house in the city for a new house in the country! While many things are new—including some scary new sounds!—there are still so many things that are the same. This sweet book reminds readers that no matter where we live, the most important things will always remain the same. 


The Day You Begin by Jacqueline Woodson, illustrated by Rafael López

This lyrical picture book addresses every child who feels left out at some point or other. Perhaps it’s because they didn’t go on trips like everyone else, maybe their lunch is different, or it could be that the games kids play at recess aren’t games the child plays well. In warm, poetic ways, this story addresses the beauty and insecurity that coexists in those moments, while offering hope for connection. This book is perfect for any child (and adult) who feels alone sometimes—which means all of us! 


Your Baby’s First Word Will Be Dada by Jimmy Fallon, illustrated by Miguel Ordóñez

Calling all dads! This book is a hilarious way to train your child to say Dada! As animal parents each take turns saying Dada, their babies don’t seem to listen… until everyone says Dada together at the end! The fun illustrations and simple repetition is sure to have your child saying Dada way more than Mom would like!


Bike On, Bear! by Cynthea Liu, illustrated by Kristyna Litten

Bear can do just about anything—except ride a bike! No matter how hard he tries, it never seems to work. But when a new community park opens that doesn’t allow training wheels, Bear is willing to do anything to hang with his friends. He heads to the library to learn all he can about bike riding. But will it be enough? This fun story is great for kids who are struggling to try new things—because sometimes all we need is a little extra push (pun intended)!


When You Can Swim by Jack Wong

Imagine all the adventures that swimming can bring! When you can swim, you can jump off bridges into the canal, see another world in the ocean, enjoy twilight swims in a pond and feel waterfalls down your back! With lyrical language and gorgeous illustrations, any child who is nervous about swimming will be ready to jump right in!


I hope you enjoyed these Ten Favorite Milestone Picture Books!

For more great ideas, feel free to check out 10 Favorite Identity Picture Books or 10 Favorite Mindfulness Picture Books!

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