First day of preschool books, and a story of their own

The best first day of preschool books are the ones that answer your child's real worry. If the worry is missing you, read Audrey Penn's The Kissing Hand, Anna Dewdney's Llama Llama Misses Mama or Martin Waddell's Owl Babies. If the worry is "what even happens there?", read Lucy Cousins' Maisy Goes to Preschool or Daniel Goes to School by Becky Friedman. Start a few weeks ahead, keep the build-up low-key, and think about adding a short homemade book that shows your own child walking into their own classroom.

Books about starting preschool, by worry

All of these are real titles available at most libraries. I have grouped them by the worry they handle, because a child scared of goodbyes needs a different book than a child who is curious about snack time.

For "I will miss you"

• The Kissing Hand by Audrey Penn. Chester Raccoon's mother kisses his palm so he can carry her love to school. Many families copy the ritual at drop-off.
• Llama Llama Misses Mama by Anna Dewdney. Little Llama is sad on his first day, joins in slowly, and Mama comes back. Very good for a child who cries at drop-off.
• Owl Babies by Martin Waddell. Three baby owls wait for their mother in the night. She comes back. That is the whole book, and it is exactly the right message for a two-year-old.
• The Invisible String by Patrice Karst. An invisible string of love connects people who are apart. Better for 4 and up.

For "what happens at preschool?"

• Maisy Goes to Preschool by Lucy Cousins. Maisy's ordinary day at preschool, from arriving to going home. Calm and concrete.
• Daniel Goes to School by Becky Friedman. Daniel Tiger's first day, built around the idea that grown-ups come back.
• Pete the Cat: Rocking in My School Shoes by Eric Litwin. Upbeat and sing-song, good for a child who needs school to sound fun.

For the worrier

• Wemberly Worried by Kevin Henkes. Wemberly worries about everything, especially school, and finds a friend who worries too. Funny for 4 and 5 year olds.

One tip from reading these at bedtime: let your child pick which one comes back. The one they ask for over and over is probably the one that names their worry.

What the sources say about getting ready

ZERO TO THREE's guide Preschool Prep: Helping Toddlers Prepare for Preschool recommends reading books about preschool over the summer and talking about how the characters feel. It also warns against making the milestone too big a deal, because a child can end up more worried than excited. Its other suggestions are practical and free:

• Play school at home. Take turns being parent, child and teacher. Act out taking off your coat, circle time, snack and saying goodbye.
• Practice self-help skills as a game: unzipping a coat, hanging it on a hook, opening the lunch box.
• Visit the school and play on its playground a few times before the first day.
• Listen to worries instead of rushing to reassure, and expect some regression, like potty accidents, during the transition.
• Start the school bedtime about two weeks before the first day.
• Pack a comfort object. A stuffed animal, blanket, family photo or favorite book can help if your child feels lonely during the day.

How to say goodbye

The American Academy of Pediatrics' guide to soothing separation anxiety boils drop-off down to a few habits:

1. A quick goodbye ritual. A special wave, triple kisses at the cubby, a kiss in the palm. Keep it short, because a long goodbye stretches the worry too.
2. The same routine every day, at the same time where possible.
3. Full attention, then go. Be warm and present while you say goodbye, then leave even if there are tears.
4. Keep your promise about coming back, and do not pop back in to check.
5. Say when, in kid time. "I'll be back after nap time and before afternoon snack," not "at 3."
6. Practice being apart beforehand, with a grandparent or a friend for an hour.

ZERO TO THREE adds that staying 15 to 30 minutes on the very first morning, if the school allows it, can help your child settle in before you leave.

Make a preschool book starring your child

Here is my favorite tip from the ZERO TO THREE guide: if your child is worried about missing you, make a book of family photos to keep in their cubby and look at when they feel lonely. You can go one step further and make a book about the preschool day itself, with your child in every picture. When I made the first coloring storybook for my own kids, what struck me was how much a page showing them doing things they knew held their attention.

A simple version, about 8 pages, one short sentence each:

1. Getting ready. Your child with their backpack by the door.
2. The drive or walk. A photo of the route or the car seat.
3. My school. The outside of the building (take it on a visit).
4. My teacher. Ask the school for a photo, or use their website.
5. Hanging up my coat. Take this one on a visit day if you can.
6. Playing. The playground or a corner of the classroom.
7. Our goodbye. Whatever your ritual is: the wave, the hand kiss.
8. Pick-up. "Mommy comes back after snack." Use your real pick-up time, in kid time.

Print it, staple it, and read it with the library books. If you want to make it into a coloring book, here is how to turn a photo into a coloring page for free, and the full method is in making a coloring book from photos.

If you would rather have one made, photo book services will print your pictures and text, and custom illustrated books will draw your child into a story. Colorkin is one of those: a 12-page coloring storybook drawn from your photos with AI illustration tools, then checked and finished by a person, so your child can color their own first day. The stapled version works just as well for the actual goal, which is a child who has already seen the day before it happens.

If preschool is landing in the same season as a move or a new sibling, see moving books for kids and new baby books for siblings. The rest of our guides for transitions are under big moments.

Questions parents ask