Books about Adjusting to Preschool for Ages 3–5 and Caregivers

By Skokie Staff Youth Services

Enjoy reading these special books together to help your child navigate the excitement and anxiety that can come with the transition to preschool.

Note: Originally developed for D69 TOPS Preschool Parent Group.

  • Heroes Wear Masks: Elmo's Super Adventure

    2020 by Sesame Workshop (COR)

    Elmo wants everyone at school to be healthy, so he wears his mask, washes his hands, and sits far apart from others during circle time.

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  • Mae's First Day of School

    2018 by Berube, Kate

    Mae’s anxiety about the first day of school has her hiding in a tree and refusing to come down. Over time, she realizes she’s not the only one who’s worried about school.

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  • Dad's First Day

    2015 by Wohnoutka, Mike

    Oliver and Dad have spent a fun summer together, but when it comes time for the first day of school, Dad discovers that he is not ready and does everything he can to postpone the big day.

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  • I Love You All Day Long

    2003 by Rusackas, Francesca

    When a little pig worries about being apart from his mother while at school, she reassures him that she’ll be loving him in every situation he endures throughout the day.

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  • Fantastic You

    2019 by Dufayet, Danielle

    Develop and nurture a loving appreciation of oneself by engaging in positive self-talk and self-compassion.

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  • Be Brave Little One

    2017 by Richmond, Marianne

    This short story with big ideas encourages children to be brave in many situations, beginning with deciding what courage means to oneself.

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  • Small

    2017 by Perry, Gina

    A little girl feels overwhelmed by the big city and everything in it, until her imagination allows her to feel big enough to accomplish anything.

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  • Someone Bigger

    2004 by Emmett, Jonathan

    Sam's dad says he is too small to fly their new kite, but when Dad, community helpers, and zoo animals get pulled into the sky, only Sam can save them.

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  • The Boy with the Big, Big Feelings

    2019 by Lee, Britney Winn

    A sensitive boy tries to hide his feelings until he meets a friend who also experiences big emotions. They learn that emotions can be big and scary, but everyone has them.

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  • Ruby Finds a Worry

    2019 by Percival, Tom

    A young girl's sense of adventure and exploration vanishes when she discovers a Worry that grows and grows until she learns how to get rid of it.

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  • Breathe with Me: Using Breath to Feel Strong, Calm, and Happy

    2018 by Gates, Mariam

    This breathing practice book teaches children breath awareness and how to use breathing in unpleasant situations to help them keep calm, relaxed, and focused. This title is also available as a downloadable video on Hoopla.

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  • Too Big or too Small?

    2017 by Leblanc, Catherine

    What's a little bear to do when he doesn't seem to be the right size for anything?

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  • You Can Do It! A Little Book about the big Power of Perseverance

    2019 by Manning, Craig

    Elmo and his friends learn to be patient and keep trying when learning new skills such as writing one’s name, riding a bike, or catching a ball.

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  • I Can Do It! A First Look at Not Giving Up

    2010 by Thomas, Pat

    This book introduces young readers to the importance of learning to do new things, even when they are very difficult, and advises them to not be afraid of failure or making mistakes.

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  • A Perfectly Messed-Up Story

    2014 by McDonnell, Patrick

    Louie becomes angry when the story in which he appears is ruined by messes from jelly, peanut butter, and other things that do not belong in books. A good reminder for overreactors that even if things are messy, they can still be just fine.

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  • Little Gorilla

    1976 by Bornstein, Ruth

    Little Gorilla's family and friends try to help him overcome his special growing pains.

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  • Bear's Big Day

    2016 by Yoon, Salina

    Bear has a tough first day at preschool without his special friend Floppy, but learns with the support of a kind and creative teacher that "being big doesn't mean you have to do everything by yourself."

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  • Ming Goes to School

    2016 by Sullivan, Deirdre

    In this gentle story, Ming learns that there is lots of fun to be had at preschool and that she can conquer her fear of the big red slide by giving herself time.

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