Book Series · 10 Books

The Kissing Hand Books

In order from The Kissing Hand to Chester Raccoon and the Almost Perfect Sleepover.

Audrey Penn's Chester Raccoon stories give young children a comforting language for separation, family changes, friendship, bravery, grief, and other big feelings.

Reviewed by the Bookroo Editors Updated August 12, 2026

Chester Raccoon and the Acorn Full of Memories

Reading order

How to Read The Kissing Hand Books

The ten books are shown in publication order. Begin with The Kissing Hand to learn Mrs. Raccoon's reassuring family ritual; the later stories reuse that secure relationship while addressing different childhood transitions.

The full picture books explore a particular challenge, while A Bedtime Kiss, A Color Game, and A Kissing Hand for Chester Raccoon are shorter board books for younger children. They are companions, not required chapters in one continuous plot.

Sources: Tanglewood's Kissing Hand series page.

For parents

What Parents Should Know

The series is designed for talking through common worries. Topics include starting school, a new sibling, moving, bullying, a loved one's death, sleeping away from home, and trying something frightening.

The treatment is gentle and adult support is always present. Chester may feel jealous, sad, worried, or scared, but each book closes with reassurance and a practical way to feel connected or capable.

Where the story begins

First Book in the Series

Sale price

$1797

Book #1 · Picture Book · Ages 3–8 · 1993

The Kissing Hand

By Audrey Penn, Ruth Harper (Illustrator)

A young raccoon learns to cope with going to school for the first time.

30 pages· 457 words· Est. 4 min read-aloud

5.8/7 Bookroo

$18.99Save 5%

Hardcover

Summary: Chester Raccoon dreads his first day of school, but his mother has a special secret to share. With the Kissing Hand, Chester can carry her love wherever he goes. Will this magical gesture ease his fears and help him face the unknown? Discover how a simple touch can transform a daunting journey into a heartwarming adventure.

In reading order

The Kissing Hand Series

10 books · Published 1993–2017

#1 in Series

Sale price

$1797

The Kissing Hand

Picture Book · Ages 3–8 · 1993

A young raccoon learns to cope with going to school for the first time.

#2 in Series

Sale price

$958

A Pocket Full of Kisses

Picture Book · Ages 4–8 · 2004

Chester Raccoon struggles with jealousy as he learns to share his mother's love with a new sibling.

#3 in Series

Sale price

$1597

A Kiss Goodbye

Picture Book · Ages 3–8 · 2007

Chester must leave his beloved home. Can a new place ever feel the same?

#4 in Series

Sale price

$1597

Chester Raccoon and the Big Bad Bully

Picture Book · Ages 4–8 · 2008

Chester faces a school bully and learns the power of friendship to transform enemies into allies.

#5 in Series

Sale price

$1597

Chester Raccoon and the Acorn Full of Memories

Picture Book · Ages 4–8 · 2009

A young raccoon learns to cherish memories after losing a friend.

#6 in Series

Sale price

$858

A Bedtime Kiss for Chester Raccoon

Board Book · Ages 0–5 · 2011

A raccoon overcomes fear of shadows with a loving gesture.

#7 in Series

Sale price

$759

A Color Game for Chester Raccoon

Board Book · Ages 0–5 · 2012

Discover a playful game to keep children entertained anywhere.

#8 in Series

Sale price

$1597

Chester the Brave

Picture Book · Ages 4–8 · 2012

A young raccoon learns to conquer fear with a simple strategy.

#9 in Series

Sale price

$858

A Kissing Hand for Chester Raccoon

Board Book · Ages 0–3 · 2014

A mother's secret kiss helps a young raccoon face separation fears.

#10

Chester Raccoon and the Almost Perfect Sleepover

#10 in Series

Sale price

$1597

Chester Raccoon and the Almost Perfect Sleepover

Picture Book · Ages 4–8 · 2017

Chester's first sleepover brings fun, but can he overcome homesickness when night falls?

Good to know

Common Questions

How many books are in the Kissing Hand series?

There are 10 books in the Kissing Hand series. It began with The Kissing Hand in 1993, and the newest book, Chester Raccoon and the Almost Perfect Sleepover, was published in 2017.