Starting school is a big milestone, bringing a mix of excitement, curiosity, and sometimes a few butterflies. Reading together is a wonderful way to help young children understand what to expect, build confidence, and spark positive conversations about this new adventure. From making friends and meeting teachers to learning classroom routines, these heartwarming picture books help make the transition to school feel a little less overwhelming—and a lot more exciting.
A great way to prepare is to start reading these stories together over the summer in the weeks before school begins. Revisiting a favourite book several times helps children become familiar with the idea of school, encourages them to ask questions, and gives them a chance to talk about how they’re feeling. It’s a simple but powerful way to build confidence and ease first-day worries.
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The Kissing Hand
by Audrey Penn (Author), Ruth Harper (Illustrator)
Probably the classic first-day-of-school book. Chester Raccoon worries about leaving home until his mother shares a family tradition that reassures him she’ll always be with him. Gentle, reassuring, and perfect for children who are anxious about separating from their parents.
Available in Hardcover & Paperback formats
Helps with: Separation anxiety and reassurance.
The Pigeon HAS to Go to School!
by Mo Willems (Author/Illustrator)
Hilarious and highly relatable. The Pigeon comes up with every excuse imaginable to avoid school before discovering it might actually be fun. Great for easing worries with humour.
Available in Hardcover & Paperback formats
Best for: Easing worries with humour.
The King of Kindergarten
by Mo Willems (Author/Illustrator)
Instead of focusing on fear, this celebrates starting school as an exciting adventure. It encourages confidence, curiosity, and pride—especially wonderful for children entering JK or SK.
Available in Hardcover & Paperback formats
Best for: Building excitement and confidence
The Invisible String
by Patrice Karst (Author), Joanne Lew-Vriethoff (Illustrator)
When children worry about being apart from the people they love, this comforting story introduces the idea of an invisible string that connects our hearts no matter how far apart we are. Gentle and reassuring, it’s a wonderful book to read before the first day of school, helping children feel secure, loved, and confident as they begin a new adventure.
Available in Hardcover & Paperback formats
Helps with: Easing separation anxiety and reassuring children they’re always connected to loved ones.
First Day Jitters
by Julie Danneberg (Author), Judy Love (Illustrator)
A fun twist on first-day nerves with a memorable ending that reminds children everyone feels a little nervous about something new. (Even adults!)
Available in Hardcover & Paperback formats
Helps with: Understanding that everyone gets nervous.
Miss Bindergarten Gets Ready for Kindergarten
by Joseph Slate (Author), Ashley Wolff (Illustrator)
A reassuring look at classroom routines and all the preparations that happen before the first day. Kids get a sneak peek at what school is really like.
Available in Hardcover & Paperback formats
Best for: Learning what to expect at school.
Llama Llama Misses Mama
By Anna Dewdney (Author)
A reassuring look at classroom routines and all the preparations that happen before the first day. Kids get a sneak peek at what school is really like.
Available in Hardcover & Boardbook formats
Best for: Coping with saying goodbye.
Reading tip: Start reading these books a week or two before school begins. Encourage your child to ask questions, talk about how the characters feel, and share what they’re most excited—or nervous—about. Familiar stories can help make a brand-new experience feel much more comfortable.
