The Best Books and a Workbook to Prepare for Kindergarten

Isn’t it so much fun to fill your classroom (or home) bookshelf with back to school books? I always loved setting up my classroom for the first day. There is an excitement in the air as you pick out the right book to read in the days leading up to kindergarten. Whether you’re a kindergarten teacher preparing a new class or a parent getting your little one ready for their first day of school, this milestone is both an exciting time and a big deal.

New friends. New routines. New school supplies. 

For young children, it’s a whole new world full of lots of exciting firsts, and yes, a few first-day jitters too.

Thankfully, picture books (and one sparkly unicorn-themed workbook) can make all the difference. Reading about relatable main characters facing new situations helps kids process big emotions, build social-emotional skills, and approach their new adventure with confidence and joy.

Let’s explore the best books for preparing for kindergarten, perfect for read-aloud time at home or in your classroom library.

The “First-Day Jitters” Everyone Feels

If you’ve ever seen a little one cling to a family member’s leg on the first day of kindergarten, you know how real those feelings can be. Even confident kids may worry about new friends, new teachers, and being away from home for the first time.

Parents often experience a version of this too. It’s that surprising mix of excitement and nervousness as they wave goodbye. Teachers, meanwhile, spend weeks setting up their kindergarten class to make that first day warm and welcoming. These are common fears, but the good news is that stories offer effective ways to calm them. Books normalize those worries, show coping strategies, and turn those big emotions into curiosity about what’s ahead.

Stories That Build Confidence and Connection

Research in early childhood education shows that reading children’s books about new experiences helps little learners understand abstract concepts like change, courage, and friendship. If the main character in a book is experiencing new things or navigating a new friendship, it gives children a little help when they are encountering the same thing. Through colorful illustrations and simple, comforting language, these great reads offer kids a preview of school life. They will discover stories from meeting new friends to tackling simple tasks like finding their cubby or unpacking school supplies. (I personally remember my daughter, Aniston, being so excited about finding out where her cubby would be!

Here’s your ultimate list of books (plus one workbook!) to make the kindergarten transition smoother for everyone.

Top Books for Preparing for Kindergarten

1. The Kissing Hand by Audrey Penn

A heartwarming story about Chester the raccoon, who feels nervous about his first day of school. His mom gives him a special “kissing hand” to remind him she’s always with him. For many years, this was the book we used to get them used to those longer school days and not seeing their families as often as they might like. I like to wear a simple costume when I read this endearing story. We’ve also followed raccoon prints around the school to get used to the layout. While we were out of the room I had my assistant place cookies on each child’s desk. They were in the shape of a hand with a little heart cut out of the middle and it made for such a great moment at the end of the scavenger hunt!
Perfect for: soothing separation anxiety and showing children it’s okay to miss home while loving their new school

2. First Day Jitters by Julie Danneberg

Sarah Jane isn’t sure she wants to go to school… until we find out she’s actually the teacher! This humorous twist makes it a hit with both young readers and kindergarten teachers. I will warn you that even though this one is a really great read, not all of my students laughed at the end when it’s revealed she is the teacher. They seemed a little confused so this one might go over some of their heads if they are too young for it. We’ve paired this with Jitter Juice. It was a simple recipe of sherbet mixed with a fizzy drink like Sprite. We drink it after spending a little time talking about how the Jitter Juice will help us get rid of any first day jitters we have!
Perfect for: showing that everyone gets first-day-of-school jitters sometimes

3. Miss Bindergarten Gets Ready for Kindergarten by Joseph Slate

Follow Miss Bindergarten as she preps her classroom, with 26 young students (one for each letter of the alphabet) arriving one by one. This book is full of fun little surprises. We like to look for Miss Bindergarten’s pet bird in each page spread. There are several really great books in this series about a field trip and the last day of kindergarten. 
Perfect for: previewing a typical day in class and making kids feel part of something exciting and organized

4. Wemberly Worried by Kevin Henkes

This young girl worries about everything especially starting school. But once she meets a kindred spirit, things don’t seem so scary. Kevin Hanks is such a great author. You’ll love this one!
Perfect for: teaching social skills and managing big emotions

5. Chrysanthemum by Kevin Henkes

A beautiful story about loving your name and learning to be proud of who you are. This is one that we usually read before graphing the amount of letters in each of our names on the board.
Perfect for: helping children celebrate individuality and practice kindness toward others.

6. The King of Kindergarten by Derrick Barnes

This young boy is ready to take on his new chapter with enthusiasm and confidence.
Perfect for: pumping up self-esteem and making school sound like the greatest adventure ever

7. The Queen of Kindergarten by Derrick Barnes

A companion story featuring a young girl who models kindness, leadership, and courage on her first day of kindergarten.
Perfect for: empowering children to shine as helpers and leaders in their kindergarten class

8. The Night Before Kindergarten by Natasha Wing

This rhyming story is a playful nod to The Night Before Christmas that helps kids imagine packing backpacks and saying goodbye.
Perfect for: preparing children for simple things like drop-off routines and bedtime anticipation

9. Kindergarten Rocks! by Katie Davis

Dexter swears he’s not scared because his older brother told him how fun school will be. (Spoiler: Dexter’s stuffed dog isn’t so sure.)
Perfect for: easing fears with humor and relatability

10. The Name Jar by Yangsook Choi

When a young student moves to a new country, she wonders if she should pick an easier name. Her classmates help her see how special her real name is.
Perfect for: fostering inclusion and understanding diverse cultures in the school season

11. Our Class Is a Family by Shannon Olsen

A warm reminder that school is more than just lessons… it’s a community! I’ve known Shannon for so many years. She is a wonderful friend and writer!
Perfect for: both parents and teachers who want to build a caring classroom culture

12. A Letter From Your Teacher: On the First Day of School by Shannon Olsen

This book’s heartfelt tone helps children see that their teacher already believes in them. Shannon nailed it again with this title!
Perfect for: starting the school year with encouragement and connection

13. The Pigeon HAS to Go to School! by Mo Willems

Pigeon lists every reason not to go… until he realizes how fun school might be. If you’ve never read books by Mo Willems to your children, get ready for a delight! They absolutely love these funny and quirky stories!
Perfect for: turning stubbornness into excitement and introducing humor to the first-day jitters conversation.

14. Clifford Goes to Kindergarten by Norman Bridwell

Clifford’s big step into school life is full of friendship, fun, and, of course, a little chaos.
Perfect for: reminding kids that learning is fun especially with friends (and furry ones).

15. What Should Danny Do? School Day by Ganit and Adir Levy

An interactive story where kids make choices for Danny and see the results play out. I’ve met Ganit and Amir and they are lovely supporters of teachers. We have all of the books in the series because my children asked to read them again and again to see how the book changes depending on the choice they made. (Remember those choose your own adventure chapter books from when we were younger? This is similar, but beautifully illustrated and SEL focused.)
Perfect for: teaching decision-making, social-emotional skills, and important lessons through play

Bonus: Kindergarten Activity Book: Unicorns! by Hilary Statum

This isn’t just another workbook. It’s colorful, interesting, and perfect to use during the summer leading up to the first day of kindergarten. It was an honor for me to write this book. I spent a lot of time thinking of fun scenarios with my sister Heidi to add to this book. 

It’s packed with fun practice pages that build letter sounds, fine motor skills, and academic readiness, Kindergarten Activity Book: Unicorns! gives kids a great way to learn through play.

The vibrant illustrations and simple tasks make it ideal for young readers who love a little sparkle while practicing for success.
Perfect for: combining learning and fun in the weeks before school starts and a perfect way for parents and teachers to prepare children for classroom routines.

Find it here: Kindergarten Activity Book: Unicorns! by Hilary Statum

Tips for Teachers + Parents

Here are a few effective ways to use these books and activities together:

For Teachers:

• Create a “First Week Read-Aloud Basket” and rotate one title each morning.
• Use Our Class Is a Family or A Letter From Your Teacher to build classroom community.
• Encourage families to read The Kissing Hand at home before the first day of kindergarten.

For Parents:

• Read one story each night in the month before school starts.
• Use my workbook to review letter sounds and fine motor practice alongside storytime.
• Ask your child to draw their favorite character or act out a typical day they imagine.

My Picks

I would be remiss if I didn’t mention a few other favorites. I love Llama Llama Back to School and Llama Llama Loves His Teacher. Anna Dewdney has always been a favorite author of mine. I also have a sweet spot for Little Critter’s First Day of School written by Mercer Mayer. I’ve been reading that classic series to my students and children at home for years and years. Mae’s First Day of School by Kate Berube also deserves a mention for helping students focus on the positives rather than being scared. Who doesn’t love Curious George titles? Curious George’s First Day of School by Margret and H.A. Rey is a must for every teacher and parent preparing young kids for the kindergarten transition. Time for School Little Blue Truck by Alice Schertle is an adorable read-aloud too. We are big fans of that entire series. Finally, you’ll definitely want to add David Shannon’s David books to your school libraries. David Goes to School and No, David are kid favorites!

Your child (or your students!) only start kindergarten once. Let’s make it as magical as possible with this fun titles.

Grab a few of these best book recommendations, add the Unicorn Activity Book, and enjoy reading your way into the new school year.

Happy Teaching and Parenting this week, friends!