Little Bookshelf: Books To Start The School Year


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One of my favorite pictures is of my oldest son standing in front of the school on the first day of kindergarten. With his giant backpack straps over both shoulders, a funky dinosaur shirt on, and a fresh haircut, he is smiling so big his cheeks are pinchable. Since then, we take a picture every year on the first day of school. Every school year marks a rite of passage. A fresh start. A time to turn all the anticipation into energy for learning.

When Jordan started kindergarten, we also started another tradition – books to start the school year. The night before the first day of kindergarten, we read The Kissing Hand by Audrey Penn with illustrations by Ruth E. Harper and Nancy M. Leak. It’s about a small raccoon who is scared to be away from his mother, but the raccoon mama kisses her little one’s paw and reminds him she is always with him. My husband and I each wrote a letter to Jordan on the inside cover of The Kissing Hand, and we read them to him the night before kindergarten started. When we shared it with him, he said, “That’s really nice.” We’ll be giving it to Danny now that he’s going to kindergarten this year.

Books to start the school year

Books to Start the School Year

Now my husband and I choose a book to give to each of our sons each year to capture the moment in time. Inside the front cover, we write our letters sharing how proud of them we are and our hopes for them that school year. We’ve chosen books that share a special message appropriate to their grade level and maturity but also might help them be brave, develop empathy and believe in their dreams. Books are magical, and talking about the characters and their experiences helps us have discussions with our own kids about how we act and treat others.

First Day Book Tradition – Kindergarten through 5th Grade

Here are the books we have chosen for kindergarten through fifth grade:

books about nocturnal animals, first day of school books

First Day of Kindergarten:

The Kissing Hand by Audrey Penn with illustrations by Ruth E. Harper and Nancy M. Leak

A small raccoon who is scared to be away from his mother finds comfort in the kisses his mama plants on his paw, a reminder she is always with him.

first day of school books

First Grade

The Story of Ferdinand by Munro Leaf with illustrations by Robert Lawson

Ferdinand is big and strong, but he would rather sit by himself on his favorite hill and smell flowers than fighting the other bulls.

books to start school

Second Grade

Extra Yarn by Mac Barnett with illustrations by Jon Klassen

When Annabelle finds a magical box of yarn, she knits sweaters for everyone and everything and finds that her generosity is invaluable.

books to start school

Third Grade

The One and Only Ivan by Katherine Applegate

Ivan, the gorilla, is resigned to his shopping mall life until a baby elephant comes to live with him and he becomes determined to help her find a better fate.

books to start the school year

Fourth Grade

The Strange Case of Origami Yoda by Tom Angleberger

Tommy and his friends debate whether the origami Yoda Dwight wears on his finger is real as they survive sixth grade.

Fifth Grade

Wonder by RJ Palacio

Up until now, Auggie hasn’t been able to attend school for medical reasons, but now he’s facing fifth grade for the first time and finding friends who accept him for who he is despite his physical differences.

We have a special shelf for these books, and I hope they’ll be stories they return to throughout their lives and maybe even share with their own kids and grandkids someday. But most importantly, I know this tradition comforts me as much as it helps my kids transition from summer to the school year.

If you want to support local businesses, here are some independent bookstores in and around Lake county that you can visit. 

Find more book suggestions on our Bookshelf!


Jen Vincent is a Technology Integration Specialist for Mundelein School District 75 who loves to stay busy and go on adventures with her two monsters, Jordan and Danny, and her sports-loving husband, Chad. As a writer, blogger and educator, she strives to model and inspire others to live a growth mindset in everything she does — be it staying in a yurt on a yoga retreat, writing a novel, or ordering a drink at Starbucks. While she loves a good Kombucha and a fresh salad, she can tell you where to get the best vegan chocolate cake and non-meat “bacon” burger in Chicagoland. Jen blogs can be found on Twitter at @mentortexts as well as

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Little Bookshelf: Books To Start The School Year

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