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Starting school is a big milestone for children, and it can be both scary and exciting! Grandparents can help with the transition by sharing books about going to school. Seeing a relatable character going through the same things helps your grandchild process those feelings!

The following picture books are the best we found for grandchildren starting a new school. Some of them address their fears, some give behind-the-scenes peeks, some share what the day will look like from the child’s point of view. From funny to touching, there’s a back-to-school story for every grandchild here.

Pirates Don't Go to Kindergarten!

by Lisa Robinson, illustrated by Eda Kaban

One of the hardest things for a child to adjust to is leaving a familiar teacher behind. This rollicking pirate tale addresses the feelings of a young girl who wants to stay with her preschool class. The empathy of teachers and kids alike help her adjust to her new classroom. The serious subject is lightened by cheerful illustrations and playful text. A delightful book to share with your grandchild.

Maisy Goes to Preschool: A Maisy First Experiences Book

by Lucy Cousins

Lucy Cousins’ colorful illustrations have been delighting small children for decades, and Maisy Goes to Preschool is no different. Children about to start preschool will get a peek into what lies ahead as they accompany Maisy on her school day. It’s the perfect choice for your young grandchild!

The Invisible String

by Patrice Karst, illustrated by Joanne Lew-Vriethoff

Long-distance grandparents love The Invisible String because it’s a great way to illustrate how their love for their grandchild connects them even when they are apart. It’s an equally good tale for children about to start school, who may be anxious about being away from their parents. If you haven’t added this classic to your grandchild’s library, the start of the school year is a perfect time.

The King of Kindergarten

by Derrick Barnes, illustrated by Vanessa Brantley-Newton

Bright illustrations and vibrant words make this story about conquering kindergarten a joy to read. Your grandchild will learn all about going to school as the main character talks about his kindergarten kingdom. It’s full of fun royal references and imagination, and just the thing for a child who loves to pretend. Check it out here.

The Queen of Kindergarten

by Derrick Barnes, illustrated by Vanessa Brantley-Newton

You’d be forgiven if you suspected The Queen of Kindergarten is a carbon copy of The King of Kindergarten with just a gender change. However, you’d be wrong. Author Derrick Barnes creates an entirely new tale, while still helping young readers understand what to expect when they start school. If you have a young queen in your family, they’ll love this book.

Barnaby Never Forgets

by Pierre Collet-Derby

The lively artwork is just part of the allure of this silly, lighthearted look at going back to school.  Barnaby the bunny is very relatable to any child who’s ever forgotten something, and children love hearing this adorable story on repeat. The illustrations are full of extra details to delight the reader. This might be the picture book your grandchild needs to celebrate the start of school.

The Day You Begin

by Jacqueline Woodson, illustrated by Rafael López

The Day You Begin introduces the idea that everyone feels out of place sometimes. The art and language make it a pleasure to read aloud.  Featuring diverse characters and cultures, it’s a perfect book for children who may worry about fitting in. If your grandchild is moving to a new school, this book is an ideal choice.

How to Get Your Teacher Ready

by Jean Reagan

Jean Reagan does it again! A comical and sweet look at all the ways a teacher might need help getting ready for the first day of school. Children will love the role-reversal and hilarious pictures, and it’s a fun book to read to them. Like her “How to Babysit” stories, How to Get Your Teacher Ready empowers kids about a situation that may seem scary.

How to Get Your Octopus to School

by Becky Scharnhorst, Illustrated by Jaclyn Sinquett

This brand-new picture book features an adorable octopus who is a little nervous about the first day of school. The sweet story is accompanied by illustrations that allow children to search and find the octopus. As a bonus, the book ends with informative facts about octopuses. If you have a nervous first-day-of-schooler, they’ll love this book.

The Kissing Hand

by Audrey Penn, Illustrated by Ruth E. Harper and Nancy M. Leak

If your grandchild is a bit nervous about starting school, get them this charming story of a young raccoon. This classic tale is just as relevant today as when it was first published thirty years ago. The gentle illustrations and love-filled story helps children see that school is a lot like home, but with even more to explore. Plus a “kissing hand” is a great ritual for when you have to part from your grand!

Miss Bindergarten Gets Ready for Kindergarten

by Joseph Slate, illustrated by Ashley Wolff

A long-time favorite, Miss Bindergarten gets ready for her students while they are getting ready for her. Told in rhyming text, the story and pictures show all the things that both teacher and students have to do to get ready for the first day of school. There’s a student for every letter of the alphabet, adding a little extra room for learning to this tale. It’s fun to read out loud, and your grands will love listening to it.

The Pigeon HAS to Go to School

By Mo Willems

The much beloved Pigeon stars in this hilarious tale about starting school. Pigeon’s feisty objections make children laugh, and they don’t even realize their own objections to starting school are being overcome along with Pigeon’s. You can’t go wrong when you get this book about first-day jitters for your grandchild.