First Day of School Books
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First Day of School Books for Preschool and Kindergarten

The first day of school can both exciting and scary for little ones, and let’s be honest, for us parents too. Transitioning to preschool or kindergarten can be a big change and this list of books will help make that change a little easier for everyone.

My oldest, Mikey is 3 and a half and will be starting preschool this fall.  He can’t stop talking about how excited he is to go on the big yellow bus, and I’m just sitting over here crying wondering why they have to grow up so fast.  At the moment it seems Mikey is more prepared for school than I am, but as it gets closer that may change, so I am armed with a supply of books to help introduce him to the idea of school.

First Day of School Books

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The Night Before Preschool
The Night Before Preschool by Natasha Wing
Little Billy is anxious about his first day of school and has some trouble sleeping. The next night he has trouble sleeping again because he made so many friends at school he can’t wait to go back the next day to see them.

Llama Llama Misses Mama

Llama Llama Misses Mama by Anna Dewdney
Llama’s Mama makes sure he is ready for his first day of school.  She makes sure he meets his new teacher, friends, and checks out the classroom, but when it comes time for Mama to leave he starts to wonder if she’ll come back. Of course, she does, but until then his new friends make sure Llama knows just how much fun school is!


Maisy Goes to Preschool

Maisy Goes to Preschool by Lucy Cousins
This book filled with colorful illustrations walks you through all the fun that Maisy has at Preschool.  Her day is filled with friends, story time, snack, and even some fun outside on the playground.  This book is a great way to show your little how much fun they will have every day at preschool.

Pete the Cat Rocking in my School Shoes

Pete the Cat: Rocking in My School Shoes by Eric Litwin
I don’t know about your kids, but mine love a good book they can sing along to.  This Pete the Cat book provides that and so much more.  Pete discovers the library, lunchroom, playground and more at his school, all while keeping his cool and rocking in his new school shoes.  If you are looking for great deals on some new school clothes for your little be sure to check out my post Back to School Deals at Gymboree.

The Night Before Kindergarten

Night Before Kindergarten by Natasha Wing
It’s the night before kindergarten and the children are dreaming of school supplies and what the first day of school will bring.  Once they get to school they find out how much fun it is and their parents are the ones who are crying and having a hard time saying goodbye, something I’m sure most of us can relate to.

Wemberly Worried

Wemberly Worried by Kevin Henkes
Wemberly is a worrier.  She worries about big things, and she worries about little things, basically, she worries about EVERYTHING, and the first day of school is no different. When Wemberly worries she likes to rub the ears of her stuffed bunny, Petal. The first day of school she meets a new friend, named Jewel, and her stuffed animal.  They quickly become inseparable and learn there really isn’t much to worry about when it comes to all the fun you’ll have at school.

The Kissing Hand  by Audrey Penn
New situations, like school, can be scary for both parents and children alike. The Kissing Hand provides a comforting message that no matter where you are, your mother’s love is always with you.  The secret of the kissing hand let’s your child know that the love and reassurance they need to conquer new things is never further away than the palm of their hand.

If You Take a Mouse to School by Laura Numeroff
If You Give a Mouse a Cookie has been a favorite in our house for a long time, so I knew If You Take a Mouse to School would be a hit and I wasn’t wrong.  Taking a mouse to school may seem like a good idea but you’ll quickly find that there is plenty of mischief to be had.  From asking to share your lunch box and backpack to practicing math and writing on the chalkboard, this little mouse knows how to have a good time.

David Goes to School by David Shannon
David’s teacher certainly has her hands full with high energy David in her class.  From chasing him down hallways to chewing gum in class, his crazy antics certainly keep her on her toes and will have even the most behaved reader laughing along.

How Do Dinosaurs Go To School? by Jane Yolen
This book is full of fun colorful illustrations and playful read-along verses. These dinosaurs are full of rambunctious childhood antics and will keep your child intrigued and delighted to keep turning the pages. This book gives great insight as to what is expected from your children and how to behave in school.


First Day Jitters by Julie Danneberg
This book starts off with Sarah Jane not wanting to get out of bed for her first day at a new school.  After some convincing from her father, she arrives at school and meets the principal, despite her fears and hesitations. This best part of this book is the surprise at the end where you find out that Ms. Sarah Jane is actually the teacher and not a student

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  1. I love these suggestions! I am thinking about sending my daughter to daycare a few days a week, and I think reading these books will definitely help her understand that I will come back for her! I’m nervous!

    1. I think it can definitely be more nerve wracking for us than our children sometimes. I hope these books help ease the transition for both of you.

  2. Great list! We love Pete the Cat and David in my kindergarten class!

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