Rediscovering the Magic of Handwritten Letters Through Classic Children's Literature

As a former kindergarten teacher turned calligraphy artist and the founder of The Cursive Connection, I've always believed that handwriting is more than just a tool for communication—it's a window into the soul. Today, I want to share with you some of my favorite children's books that beautifully demonstrate the magic and importance of handwritten correspondence, and how these timeless stories can inspire your own cursive journey.

The Power of Letters in Children's Literature

There's something truly special about books that celebrate the art of letter writing. These stories don't just entertain; they teach children about the thoughtfulness, care, and personal touch that comes with putting pen to paper. In our digital age, where texts and emails dominate our communication, these books serve as gentle reminders of what we're losing when we abandon the written word.

Featured Books That Celebrate Letter Writing

The Jolly Postman Series

The Jolly Postman: The Jolly Postman This innovative interactive book by Janet and Allan Ahlberg revolutionized children's literature when it was first published in 1986. What makes this book so special? It actually contains real letters tucked into envelope pages that children can remove and read! The jolly postman delivers mail to beloved fairy tale characters like the Three Bears, Cinderella, and the Big Bad Wolf. Each letter is written in a different style and serves different purposes—from Goldilocks's apology letter to the Three Bears to a circular from a witch's catalog.

The Jolly Christmas Postman The beloved sequel continues the magic with Christmas-themed correspondence between fairy tale characters. This book won the Kate Greenaway Medal and shows how seasonal celebrations can inspire beautiful letter writing.

Other Notable Books

Dear Mr. Blueberry This charming story follows a young girl's correspondence with her teacher about whales. The back-and-forth letter format shows children how letter writing can be used for learning and asking questions.

Dear Peter Rabbit A delightful collection of letters between familiar storybook characters that encourages children to think creatively about the relationships between different fictional worlds.

Yours Truly, Goldilocks This book reimagines the classic fairy tale through the lens of correspondence, showing how letters can tell stories and resolve conflicts.

Letters from the North Pole Features actual pull-out letters from Santa Claus, making the magic of receiving mail tangible for young readers.

Why These Books Matter for Cursive Education

As someone who has dedicated her career to preserving the art of beautiful handwriting, I see these books as invaluable teaching tools. Here's why they're perfect companions to cursive education:

1. They Make Letter Writing Purposeful

Children learn best when they understand the "why" behind what they're learning. These books show that letters aren't just school exercises—they're real forms of communication that can express emotions, share news, ask questions, and build relationships.

2. They Demonstrate Different Letter Formats

From formal invitations to casual postcards, these books expose children to various types of written correspondence. This variety helps them understand that cursive isn't just for copying sentences—it's for real-life communication.

3. They Connect Reading and Writing

When children see characters they love engaged in letter writing, it creates a natural bridge between reading comprehension and writing skills. They begin to understand that the stories they love to read can inspire the letters they write.

4. They Preserve Traditional Communication

In a world where handwritten letters are becoming rare, these books serve as time capsules, showing children what personal, thoughtful communication looks like.

Incorporating These Books into Your Cursive Journey

Whether you're using The Cursive Connection curriculum or simply want to inspire a love of handwriting in your children, here are some ways to use these books:

For Homeschool Families:

  • Read these books aloud during your literature time

  • Use them as inspiration for writing practice—have children write their own letters to fairy tale characters

  • Create envelope pages in your child's writing notebook for storing their practice letters

  • Use the different letter formats as models for teaching various types of correspondence

For Teachers:

  • Include these books in your classroom library

  • Use them to launch letter-writing units

  • Create cross-curricular connections between literature and handwriting instruction

  • Have students analyze the different handwriting styles shown in the illustrations

For Parents:

  • Start a family letter-writing tradition inspired by these books

  • Encourage children to write letters to grandparents, friends, or even fictional characters

  • Use the books as bedtime stories that spark conversations about communication

  • Create special stationery for your children to encourage letter writing

The Simply Lettered Connection

At Simply Lettered Studio and through our online shop, we believe that words never lose their value. These cherished children's books prove that point beautifully. They show us that a handwritten message—whether it's a note from Goldilocks apologizing to the Three Bears or a child's first letter to Santa—carries weight and meaning that digital communication simply cannot match.

The tactile experience of opening an envelope, unfolding a letter, and seeing someone's handwriting creates a connection that transcends time. These books teach children (and remind adults) that taking the time to write by hand shows true thought, care, and importance.

Inspiring the Next Generation

As we work to preserve cursive writing through programs like The Cursive Connection, these books serve as powerful allies. They show children that handwriting isn't just an old-fashioned skill—it's a timeless way to connect with others, express creativity, and leave a lasting impression.

When children see the joy on the faces of fairy tale characters receiving mail, they begin to understand the magic they can create with their own pens. They learn that their handwriting has the power to make someone's day brighter, to preserve memories, and to create keepsakes that will be treasured for generations.