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6 Extraordinary Picture Books About Kids and Their Grandparents

Read these special stories about kids and their grandparents

By Olivia Gentile

(This article previously appeared on

This winter, I read all the picture books I could find about children and their grandparents.

Here are my favorites.

These books aren’t just stunningly written and illustrated. They also get the new American family.


The Hello, Goodbye Window

A little girl’s visits with her grandparents revolve around their roomy kitchen, where the three of them cook, eat, color and pretend to see dinosaurs out the window.

“Mommy and Daddy pick me up after work. I’m glad because I know we’re going home, but it makes me sad too because I have to leave Nanna and Poppy. You can be happy and sad at the same time, you know. It just happens that way sometimes.”

Nanna is black and Poppy is white, but the author doesn’t make a big deal of that. The big deal is the attention they both lavish on their granddaughter.

Written by Norton Juster; illustrated by Chris Raschka and Michael Di Capua.

Good for babies, preschoolers and grade-schoolers.


The Matchbox Diary

A century ago, when most Americans only lived into their 60s, great-grandparents were scarce.

Not anymore.

In this book, a kindergartener, who lives out West, visits her great-grandfather on the East Coast.

He shows her dozens of treasures that he stashed in matchboxes as a little boy, including an olive pit from his hometown in Italy, a hairpin he found when he and his family were on the boat to America and a ticket to a baseball game in Philadelphia.

“That’s my favorite box,” the man tells his great-granddaughter. “My first baseball game. I didn’t understand it, why the men were running. But I was in heaven not to be working and to sit by my father.”

The last page of the book shows the girl returning home in an airplane. In her lap is the “diary” she’s just started: an empty candy box that, so far, holds a Lego piece and a stewardess’s pin.

Written by Paul Fleischman; illustrated by Bagram Ibatoulline.

Good for preschoolers and grade-schoolers


Coming On Home Soon

These days, when parents deploy abroad or travel for business, children often stay with their grandparents. That’s why this poignant book, which takes place during World War II, will resonate with so many families.

“Mama’s hands are warm and soft.

When she put her Sunday dress into the satchel, I held my breath.

Tried hard not to cry.

Ada Ruth, she said. They’re hiring colored women in Chicago since all the men are off fighting in the war.

Mama folded another dress and put it in the bag.

I’m gonna head on up there.

Then she pulled me close up to her, pressed her face against mine.

Make some money I can send on home to you.”

Ada Ruth is left in the care of her grandmother, who’s stern and reserved compared to Mama. But over time, Ada Ruth and Grandma form a tender bond.

The last page of the book shows Mama trudging through the snow toward the house, just a few footsteps from a reunion with her daughter and her mother.

Written by Jaqueline Woodson; illustrated by E.B. Lewis.

Good for grade-schoolers.


Nana In the City

When a little boy from a small town spends the night at his grandmother’s apartment in New York City, he’s intimidated by the crowds, the noise and the homeless people.
“I love my nana, but I don’t love the city,” he narrates. “The city is filled with scary things.”

So Nana stays up late knitting a fancy red cape to make her grandson feel like a superhero, and the next day, he wears it out on the town.

Like many grandparents nowadays, Nana is urbane. She takes the boy to hear some street musicians and watch a break-dancer. She coaxes him to pet a pack of dogs being led by a dog-walker.

And when grandmother and grandson pass a food cart, she buys some hot pretzels and hands them to a homeless man.


“The city is busy, the city is loud and it is the absolute perfect place for a nana to live,” the boy concludes. “And for me to visit!”

Written and illustrated by Lauren Castillo.

Good for babies and preschoolers.


Lucky Pennies and Hot Chocolate

This story is told in the first person, and both the text and pictures will trick kids into thinking that the narrator is a boy who’s excited to see his grandfather.

“My favorite person in the world is coming for a visit,” the book begins. “I have a whole bunch of new knock-knock jokes for him.”

The narrator then describes all the fun things he and his “favorite person” will do together:

“I can’t wait to show him that huge hole they’ve dug down the street! I like to watch big machines moving the earth, doing their jobs.”

“I invented a new pancake recipe to try out. Super-scrumptious banana-raisin-marshmallow-surprise pancakes. I think he’ll like them.”

Only on the last page will kids realize that the narrator isn’t the boy — it’s his exuberant grandpa.

Age doesn’t define us, the author seems to be saying.

Love does.

Written by Carol Diggory Shields; illustrated by Hiroe Nakata.

Good for babies and preschoolers.



For millions of kids, summertime means visits with grandparents. They’ll relate to this autobiographical book, in which the author, who grew up in New Jersey, recalls his annual stays at his grandparents’ farm in Cottondale, Fla., in the 1940s and ‘50s.

Every year, when the author, his mother and his siblings arrived, “Bigmama and Bigpapa were waiting for us on the porch. There were hugs and kisses and ‘Oh my, how you’ve grown!’ and ‘How tall you are … is this you?”

“Then off with our shoes and socks. We wouldn’t need them much in the next few weeks.”

Later, at dinnertime: “Everybody sitting around the table that filled the room — Bigmama, Bigpapa, Uncle Slank, our cousins from down the road and all of us. We talked about what we did last year. We talked about what we were going to do this year. We talked so much we hardly had time to eat.”

“The night was jet black except for millions of stars. We could hardly sleep thinking about things to come.”

The last page shows a grown man lying in bed at sunset. An urban skyline is visible from the window.

“Some nights even now, I think that I might wake up in the morning and be at Bigmama’s with the whole summer ahead of me.”

Written and illustrated by Donald Crews.

Good for preschoolers and grade-schoolers.

(With thanks to the staff at Bank Street Book Store and to the librarians in my life, Andrea Dolloff and Carrie Silberman, for steering me toward these and other titles. I’d also like to thank my daughter, Madeline, for vetting dozens of books with me.)

Olivia Gentile is an author, journalist, and mother in New York City. She launched The Grandparent Effect to honor her grandparents, who thrived into her 30s and their 90s. She's also started a discussion about the extended American family on Facebook. Read More
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