
Some of my favorite stories are from middle grade books with intergenerational friendships and relationships. While I already have a list of books about grandparent relationships, the books on today’s list highlight friendships between tweens and older characters (middle-aged and up). In these heartwarming stories, the friendship with an older individual changes the perspectives and lives of both parties in remarkable ways. If you’re up for reading books deserving of a hug, these are your picks.
Best Middle Grade Books with Intergenerational Friendships
Here are 15 best middle grade books with intergenerational friendships:
These Unlucky Stars
Ever since her mother left a few years ago, Annie has felt like the odd one out in her family. Her dad and brother are practical and organized–they just don’t understand the way she thinks, in lines and color. Everywhere she turns, she feels like an outsider, even at school, so she’s been reluctant to get close to anyone.
When a “Ding-Dong-Ditch” attempt goes wrong, Annie finds herself stuck making amends with Gloria, the eccentric elderly lady she disturbed. As she begins to connect with Gloria and her weird little dog, it becomes clear that Gloria won’t be able to live on her own for much longer. But it’s this brief and important friendship that gives Annie the confidence to let people in, and see how rich life can be when you decide to make your own luck and chart your own path to happiness.
Macy McMillian and the Rainbow Goddess
Sixth grade is coming to an end, and so is life as Macy McMillan knows it. Already a “For Sale” sign mars the front lawn of her beloved house. Soon her mother will upend their perfect little family, adding a stepfather and six-year-old twin stepsisters. To add insult to injury, what is Macy’s final sixth grade assignment? A genealogy project. Well, she’ll put it off – just like those wedding centerpieces she’s supposed to be making.
Just when Macy’s mother ought to be understanding, she sends Macy next door to help eighty six-year-old Iris Gillan, who is also getting ready to move – in her case into an assisted living facility. Iris can’t pack a single box on her own and, worse, she doesn’t know sign language. How is Macy supposed to understand her? But Iris has stories to tell, and she isn’t going to let Macy’s deafness stop her. Soon, through notes and books and cookies, a friendship grows. And this friendship, odd and unexpected, may be just what Macy needs to face the changes in her life.
Mr. Marsworth
When eleven-year-old Reenie Kelly’s mother passes away, she and her brothers are shipped off to live with their grandmother. Adjusting to life in her parents’ Midwestern hometown isn’t easy, but once Reenie takes up a paper route with her older brother Dare, she has something she can look forward to. As they introduce themselves to every home on their route, Reenie’s stumped by just one—the house belonging to Mr. Marsworth, the town recluse. When he doesn’t answer his doorbell, Reenie begins to leave him letters. Slowly, the two become pen pals, striking up the most unlikely of friendships.
Through their letters, Reenie tells of her older brother Billy, who might enlist to fight in the Vietnam War. Reenie is desperate to stop him, and when Mr. Marsworth hears this, he knows he can’t stand idly by. As a staunch pacifist, Mr. Marsworth offers to help Reenie. Together, they concoct a plan to keep Billy home, though Reenie doesn’t know Mr. Marsworth’s dedication to her cause goes far beyond his antiwar beliefs.
In this heartwarming piece of historical fiction, critically acclaimed author Sheila O’Connor delivers a tale of devotion, sacrifice, and family.
Walking with Miss Millie
Alice is angry at having to move to Rainbow, Georgia—a too small, too hot, dried-up place she’s sure will never feel like home. Then she gets put in charge of walking her elderly neighbor’s dog. But Clarence won’t budge without Miss Millie, so Alice and Miss Millie walk him together.
Strolling with Clarence and Miss Millie quickly becomes the highlight of Alice’s day and opens her eyes to all sorts of new things to marvel over. During their walks, they meet a mix of people, and Alice sees that although there are some bullies and phonies, there are plenty of kind folks, too. Miss Millie shares her family’s story with Alice, showing her the painful impact segregation has had on their town. And with Miss Millie, Alice is finally able to express her own heartache over why her family had to move there in the first place.
Tamara Bundy’s beautifully written debut celebrates the wonder and power of friendship: how it can be found when we least expect it and make any place a home.
Simon B Rhymin
Eleven-year-old Simon Barnes dreams of becoming a world-famous rapper that everyone calls Notorious D.O.G. But for now, he’s just a Chicago fifth grader who’s small for his age and afraid to use his voice.
Simon prefers to lay low at school and at home, even though he’s constantly spitting rhymes in his head. But when his new teacher assigns the class an oral presentation on something that affects their community, Simon must face his fears.
With some help from an unexpected ally and his neighborhood crew, will Simon gain the confidence to rap his way to an A and prove that one kid can make a difference in his ‘hood?
Dwayne Reed is a Chicago teacher, whose viral back-to-school music video “Welcome to the 4th Grade” took the internet by storm. His debut novel, Simon B. Rhymin’ , inspires young readers everywhere to use their voice to create change within their communities.
The Vanderbeekers of 141st Street
The Vanderbeekers have always lived in the brownstone on 141st Street. It’s practically another member of the family. So when their reclusive, curmudgeonly landlord decides not to renew their lease, the five siblings have eleven days to do whatever it takes to stay in their beloved home and convince the dreaded Beiderman just how wonderful they are. And all is fair in love and war when it comes to keeping their home.
All You Knead Is Love
Twelve-year-old Alba doesn’t want to live with her estranged grandmother in Barcelona. But her mother needs her to be far, far away from their home in New York City. Because this is the year that her mother is going to leave Alba’s abusive father. Hopefully. If she’s strong enough to finally, finally do it. Alba is surprised to find that she loves Barcelona, forming a close relationship with her grandmother, meeting a supportive father figure, and making new friends. Most of all, she discovers a passion and talent for bread baking. When her beloved bakery is threatened with closure, Alba is determined to find a way to save it–and at the same time, she may just come up with a plan to make their family whole again. From the author of How to Make Friends with the Sea comes a heartfelt story of finding one’s chosen family, healing, and baking.
Beverly, Right Here
Beverly put her foot down on the gas. They went faster still.
This was what Beverly wanted — what she always wanted. To get away. To get away as fast as she could. To stay away.
Beverly Tapinski has run away from home plenty of times, but that was when she was just a kid. By now, she figures, it’s not running away. It’s leaving. Determined to make it on her own, Beverly finds a job and a place to live and tries to forget about her dog, Buddy, now buried underneath the orange trees back home; her friend Raymie, whom she left without a word; and her mom, Rhonda, who has never cared about anyone but herself. Beverly doesn’t want to depend on anyone, and she definitely doesn’t want anyone to depend on her. But despite her best efforts, she can’t help forming connections with the people around her — and gradually, she learns to see herself through their eyes.
The Lonely Heart of Maybelle Lane
Eleven-year-old Maybelle Lane collects sounds. She records the Louisiana crickets chirping, Momma strumming her guitar, their broken trailer door squeaking. But the crown jewel of her collection is a sound she didn’t collect herself: an old recording of her daddy’s warm-sunshine laugh, saved on an old phone’s voicemail. It’s the only thing she has of his, and the only thing she knows about him.
Until the day she hears that laugh–his laugh–pouring out of the car radio. Going against Momma’s wishes, Maybelle starts listening to her radio DJ daddy’s new show, drinking in every word like a plant leaning toward the sun. When he announces he’ll be the judge of a singing contest in Nashville, she signs up. What better way to meet than to stand before him and sing with all her heart?
But the road to Nashville is bumpy. Her starch-stiff neighbor Mrs. Boggs offers to drive her in her RV. And a bully of a boy from the trailer park hitches a ride, too. These are not the people May would have chosen to help her, but it turns out they’re searching for things as well. And the journey will mold them into the best kind of family–the kind you choose for yourself.
Out of Place
Twelve-year-old Cove Bernstein’s year has gone from bad to worse. First, her best friend, Nina, moved from Martha’s Vineyard to New York City. Then, without Nina around, Cove became the target of a bullying campaign at school. Escape seems impossible.
But opportunities can appear when you least expect them. Cove’s visit to a secondhand clothing store leads her to a surprising chance to visit Nina, but only if she can win a coveted place in a kids-only design competition. Cove doesn’t know how to sew, but her friend at the retirement home, Anna, has promised to teach her. And things start really looking up when a new kid at school, Jack, begins appearing everywhere Cove goes.
Then Cove makes a big mistake. One that could ruin every good thing that has happened to her this year. One that she doesn’t know how to undo.
Wonderland

Mavis Jeeter is fearless and bold, but she has never lived in one place long enough to have a real best friend. Her flighty mother has uprooted them again to another new home and taken a job as a housekeeper for the Tully family. Mavis wants this home to be permanent—which means finding herself a best friend.
Rose Tully is a worrier who feels like she doesn’t quite fit in with the other girls in her neighborhood. Her closest friend is Mr. Duffy, but he hasn’t been himself since his dog died. Rose may have to break a few of her mother’s many rules to help Mr. Duffy—and find someone who really understands her.
Henry has run away from home, but he craves kindness and comfort—and doesn’t know where to look for them.
When Mavis and Rose hatch a scheme to find Mr. Duffy a new dog, their lives and Henry’s intersect—and they all come to find friendship in places they never expected.
The Reckless Club
On the last day of middle school, five kids who couldn’t be more different commit separate pranks, each sure they won’t be caught and they can’t get in trouble. They’re wrong. As punishment, they each have to volunteer one beautiful summer day-the last one before school-at Northbrook Retirement and Assisted Living Home, where they’ll push creamed carrots into toothless mouths, perform the world’s most pathetic skit in front of residents who won’t remember it anyway, hold gnarled hands of peach fuzzed old ladies who relentlessly push hard candies, and somehow forge a bond with each other that has nothing to do with what they’ve done and everything to do with who they’re becoming. All the action takes place in the course of this one day, with each chapter one hour of that day, as the five kids reveal what they’ve done, why they did it, and what they’re going to do now.
The Unforgettable Guinevere St. Clair
Guinevere St. Clair is going to be a lawyer. She was the fastest girl in New York City. She knows everything there is to know about the brain. And now that she’s living in Crow, Iowa, she wants to ride into her first day of school on a cow named Willowdale Princess Deon Dawn.
But Gwyn isn’t in Crow, Iowa, just for royal cows. Her family has moved there, where her parents grew up, in the hopes of jogging her mother Vienna’s memory. Vienna can no longer remember anything past the age of thirteen, not even that she has two young daughters. Gwyn’s father is obsessed with finding out everything he can to help his wife, but Gwyn’s focused on problems that seem a little more within her reach. Like proving that the very strange Gaysie Cutter who lives next door is behind the disappearance of her only friend, Wilbur Truesdale.
Gwyn is sure she can crack the case, but when she does she finds that not all of her investigations lead her to the places she would have expected. In fact they might just lead her to learn about the mother she’s been doing her best to forget…
Honeybees and Frenemies
It’s the summer before eighth grade and Flor is stuck at home and working at her family’s mattress store, while her best friend goes off to band camp (probably to make new friends). It becomes even worse when she’s asked to compete in the local honey pageant. This means Flor has to spend the summer practicing her talent (recorder) and volunteering (helping a recluse bee-keeper) with Candice, her former friend who’s still bitter about losing the pageant crown to Flor when they were in second grade. And she can’t say no.
Then there’s the possibility that Flor and her family are leaving to move in with her mom’s family in New Jersey. And with how much her mom and dad have been fighting lately, is it possible that her dad may not join them? Flor can’t let that happen. She has a lot of work to do.
The Heart and Mind of Frances Pauley
Eleven-year-old Frances is an observer of both nature and people, just like her idol, the anthropologist Margaret Mead. She spends most of her time up on the rocks behind her house in her “rock world,” as Alvin, her kindhearted and well-read school bus driver, calls it. It’s the one place where Frances can truly be herself, and where she doesn’t have to think about her older sister, Christinia, who is growing up and changing in ways that Frances can’t understand.
But when the unimaginable happens, Frances slowly discovers that perhaps the world outside her rugged, hidden paradise isn’t so bad after all, and that maybe–just maybe–she can find connection and camaraderie with the people who have surrounded her all along.
Original, accessible, and deeply affecting, April Stevens’s middle-grade debut about an unforgettable girl and an unlikely friendship will steal your heart.
There they are: 15 of the best middle grade books with intergenerational friendships! How many of these have you read? Which ones would you recommend — and which ones did I miss?
Many thanks to today’s sponsor, The Magical Imperfect by Chris Baron, a special verse novel set in 1989 about unlikely friendships, body image, and intergenerational relationships. The Magical Imperfect is out June 15. Thank you for supporting the authors and brands who keep Reading Middle Grade going.
Pin This Post – Best Middle Grade Books with Intergenerational Friendships

This is a great list. Thanks.
My pleasure, Rosi 🙂