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Books:
School Transitions

Books to help with starting school, saying goodbye, classroom worries, and feeling ready for what comes next.

Start Here

Simple, reassuring books that help children picture what school will look like: the classroom, the teachers, the routines, and the goodbye. A good first stop when you want to make the transition feel more familiar.
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LOLA GOES TO SCHOOL
 

A ssimple first-school story that shows the whole arc of the day: getting ready, saying goodbye, being in the classroom, and coming back together after school. A great place to start for preschoolers who like to know what to expect.
Ages: 2.5-5

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ROSIE GOES TO PRESCHOOL

Start Here

A gentle preschool preview that walks through the routines of the day in a clear, reassuring way. Especially helpful for children who do better when they can picture what is going to happen.

Ages: 2.5-5

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PRESCHOOL, HERE I COME!
 

 ParentFavorite

A bright, upbeat book that introduces the classroom, teachers, friends, and daily activities. Nice for building excitement without pretending that starting school is always easy.
Ages: 2.5-5

For Separation Worries

Books for children who are having a hard time with goodbye. These help name the feelings, offer reassurance, and give kids a concrete way to remember that their grown-up comes back.
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THE KISSING HAND

Start Here

A classic for separation anxiety. It gives children a small, memorable ritual they can carry with them when saying goodbye feels hard.
Ages: 3-6

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THE PIGEON HAS TO GO TO SCHOOL

 ParentFavorite

Funny and very relatable for kids who are nervous, resistant, or full of “what ifs.” Pigeon names the worries in a playful way, which can make anxious feelings easier to talk about.
Ages: 3-6

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BYE BYE TIME

A simple, comforting book about saying goodbye and knowing grown-ups come back. Better for younger toddlers starting daycare, preschool, or a new caregiver situation.
Ages: 1.5-4

For Big School Feelings

Books for the child who is nervous, resistant, unsure, or full of “what ifs.” These stories use humor and honesty to make worries feel less scary and easier to talk about.
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HOW DO DINOSAURS GO TO SCHOOL?

A playful way to talk about school behavior, routines, and expectations without sounding lecture-y. Good for kids who are worried, impulsive, or unsure how they’re “supposed” to act at school.Ages: 3-6

WE DON"T EAT OUR CLASSMATES

 ParentFavorite

A funny book about impulse control, friendship, and learning how to be part of a classroom community. It is less about first-day nerves and more about navigating other kids.
Ages: 3-6

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THE DAY YOU BEGIN

A beautiful book for children who feel different, shy, new, or unsure where they fit. Better for older preschoolers and elementary kids than very young toddlers.
Ages: 4-8

Classroom Community

Books that help children understand the social side of school: meeting new kids, learning classroom expectations, feeling included, and finding their place in a group.
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OUR CLASS IS A FAMILY

A reassuring book about the classroom as a safe, caring community. Good for children who worry about the teacher, new classmates, or whether school will feel comfortable.

.Ages: 3-7

KINDERGARTEN, HERE I COME!

A cheerful kindergarten-specific book that helps kids get excited about the transition. Best for children moving from preschool into kindergarten rather than starting preschool for the first time.

Ages: 4-6

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West Village, NY​

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