Back-to-School Books Filled with Lessons and Fun

By Jessica Schwartz | August 25, 2023

The beginning of the new school year brings with it excitement and sometimes trepidation. One of the best ways to ease anxiety is spending time with your child while being open and honest about their feelings. Reading together is a great family activity, and books can help illustrate that your child’s feelings are normal. To help, we’ve compiled a list of books that show characters experiencing some of the same fears and anxiety your child might be feeling as the new school year approaches. In these colorful stories, the characters explore the first 100 days of a new grade, play hide-and-seek with an anxious octopus, and celebrate Lunar New Year with a group of friends.

How to Get Your Octopus to School by Becky Scharnhorst

A wiggly, wily octopus would rather stay home and play, but fun awaits this adorable Cephalopod if you can just get him to school! First, you’ll have to find him and sooth his jittery nerves. In this adorable book with colorful illustrations, children can relate to this adorable creature and identify with his anxieties around starting the school year. In addition, this book will prime kids for learning with fun science facts about octopuses.

The Day You Begin by Jaqueline Woodson

Walking into a room and immediately feeling different can be scary. Lyra experiences this on her first day of school but, as she shares her own story, she realizes that she and her classmates really aren’t so different after all. This beautiful book from National Book Award Winner, Jaqueline Woodson, will fill the entire family with joy. More importantly, it teaches kids that finding the courage to share their story will help them build relationships with their peers and diminish the feeling of being alone.

A New School for Charlie by Courtney Dicmas

The adorable dog, Charlie, is excited for school. But when he walks in, he finds something he never expected – the school is full of cats. Charlie, like many in similar situations, starts to feel self-conscious. This story will help children learn how to navigate differences, especially those they haven’t experienced before.

All Are Welcome by Alexandra Penfold

In this school all are welcome. While the students may look different, celebrate different holidays, and eat different foods, they share one important trait – humanity. This is a book about acceptance and celebrating diversity. And, because it follows a groups of kids through their school day, it is a great back-to-school pick.

Harry versus the First 100 Days of School by Emily Jenkins

The transition from grade to grade can be a big challenge for any kid, but the transition from kindergarten to first grade can feel like a giant step for such small feet. In this adorable book, Harry learns a lot of lessons in his first 100 days as a first grader. His lessons run from overcoming first-day nerves to what a silent “e” is, to learning that that class guinea pig isn’t as scary as he thought. Harry can help kids navigate those first scary few months of school and remind them to reflect on all that they have learned and experienced.