6 Kids Books to Make the First Day of School Easier

I remember my first day of Kindergarten quite clearly. It was 1976 and my grandmother had made me the cutest ABC dress in the history of dresses. Oh, there was some drama – when my mother took me to get my haircut at the local beauty school and they had to cut most of it off because the girl cutting my hair was a bit too green. But, going to school was not a problem.
I was out the door as fast as my legs would take me, hit the classroom with a smile and…missed my mom and dad so badly after about 20 minutes that they had to come and get me.
The drama kicked in trying to get me out the door for day #2.
Starting school – whether preschool or that remarkable first day of Kindergarten – is such a huge moment in kids lives (ours too). There’s a lot that comes with the freedom of learning and making friends on their own.
Stories can often be a great way to plug kiddos into how things will play out, let them feel like they aren’t alone and give them some special connections to family that go anywhere with them.
We are not quite ready for school around here. But, I set out on a mission recently to collect some of the great stories parents and kiddos are digging these days as they set off into classrooms everywhere for the first time.
Always the critic, I read through more than a dozen of them the last couple of weeks and found six absolute gems that range from the sentimental to the hilarious – all available at the library, your local independent book seller or other locations (which I’ll mention as we go through them) right now.
Here they are, in no particular order:
1. Wemberly Worried by Kevin Henkes.

Wemberly is worry wart. She’s a little nervous when it comes to just about everything in her life and caution is key as far as she’s concerned. This sweet pea is particularly nervous about fitting in the first day of nursery school. The charming story never quite finds Wemberly unworried. But, all is good after friends help her find her way.
2. The Kissing Hand by Audrey Penn.

I am a big sucker for sweetness. So, when Chester Raccoon’s mom gives him a kiss on the hand to take with him everywhere, I am forced to tears. Penn’s classic about overcoming separation anxiety is my number one favourite ever. We read it all the time, using the kissing hand as a great tool for when the tiny person is upset about anyone she loves going away.
3. Miss Bindergarten Gets Ready for Kindergarten by Joseph Slate.

The whole Miss Bindergarten series is absolutely charming. But, this story is all about turning the blahs into something beautiful when Miss Bindergarten (who is particularly upbeat and funny) turns a dark classroom into a bright, cheerful learning centre. All of the kiddos are getting ready too. So, this is a perfect story for getting kids into the routine of school.
4. Don’t Eat The Teacher by Nick Ward.

Every time I read this story I think of our pal Kaden, who would think it one of the funniest ever. Sammy the shark, well, he has a bit of an issue with biting things when he gets all excited. This silly story is all about him trying to maneuver through the first day of school, with some biting-related bumps along the way. I love it.
5. How Do Dinosaurs Go To School by Jane Yolen, illustrated by Mark Teague.

Written by one of the great young adult sci-fi authors, this hilarious story about a crew of dinosaurs who are having a tough time figuring out how to fit in at school, is an absolute winner for the kiddo crowd that is in need of something funny instead of gushy. I find this a particularly good read for the boy crowd who doesn’t REALLY want anyone to know that they will be missing mom and dad, but need a little extra reassurance that school will be great. Pam over at Planet Kids in downtown Comox has this one in stock.
6. The Little Engine That Could by Watty Piper

If you lean more toward the classics, this one is the ultimate timeless back-to-school story. What better way to get nervous kiddos prepped for the big day than to give them such a positive mantra and lots of hope to help them make it over the hill. I love this story and the original illustrations. You can’t go wrong.
Category: ARTS & LITERACY, Rainy Day Book Club










I love the story Wemberly Worries. Pretty much anything by Kevin Henkes is a hit in our house!
He’s way up there for us too Shawna. Such lovable characters!:)
We love Sammy the Shark – we have “Don’t eat the babysitter” CHOMP
Thanks so much! This came at just the right time. We are in definite need of some great getting-ready-for- school stories.
Thank you for the suggestions Robin! We will go for a visit to Planet Kids this week to check out the dino book!