The best road trip novels with women in the driver’s seat

Deborah K. Shepherd Author Of So Happy Together
By Deborah K. Shepherd

Who am I?

In the ‘60s, everyone was reading—or claiming to have read—Jack Kerouac’s On the Road. I faked reading it, to appear cool. The idea of a road trip, though—characters running away, running toward, or often both—and the self-discovery that ensues—was so intriguing, I made it the heart of the novel I first drafted decades ago. I wrote about a middle-aged woman who flees her life to find a lost love and her lost youth, then put the manuscript away. For 30 years. When I retired from my social work career, I pulled it from the closet, revised it, and became an author at 74. 


I wrote...

So Happy Together

By Deborah K. Shepherd,

Book cover of So Happy Together

What is my book about?

Set in the sex, drugs, and rock ‘n roll ‘60s, when drama students Caro Mills and Peter MacKinley were kooky, colorful, and inseparable, and in the suburban ‘80s, when Caro’s creative spark has been quenched to serve the needs of her husband, Jack, and their children, So Happy Together explores the conundrum of love and sexual attraction, creativity, and family responsibilities, and what happens when they are out of sync. It’s a road trip story of missed opportunities, the possibility of second chances, and what we leave behind, carry forward, and settle for when we choose. It sits in that raw, messy, confounding, beautiful place where love resides.

The books I picked & why

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Rules of the Road

By Joan Bauer,

Book cover of Rules of the Road

Why this book?

A YA novel must be every bit as well-writtenwith thoroughly developed characters and an absorbing plotas an adult novel, and maybe more so, given an adolescent’s interest is often pulled to TikTok, Instagram, and Snapchat, not to books. Sixteen-year-old Jenna Boller’s only had her license for six months when Madeline Gladstone, president of the shoe store chain where Jenna works, taps her to be her driver for the summer. They set out on a cross-country road trip to check on the stores, but both learn unexpected lessons about each other and about themselves in the process. I love the cross-generational relationship that develops, and that gawky, self-conscious, and insecure Jenna comes into her own in a most surprising way: Like Dorothy with the ruby slippers, Jenna finds she’s had the power all along.

Rules of the Road

By Joan Bauer,

Why should I read it?

1 author picked Rules of the Road as one of their favorite books, and they share why you should read it.

What is this book about?

Meet Jenna Boller, star employee at Gladstone's Shoe Store in Chicago. Standing a gawky 5'11'' at 16 years old, Jenna is the kind of girl most likely to stand out in the crowd for all the wrong reasons. But that doesn't stop Madeline Gladstone, the president of Gladstone's Shoes 176 outlets in 37 states, from hiring Jenna to drive her cross country in a last ditch effort to stop Elden Gladstone from taking over his mother's company and turning a quality business into a shop-and-schlock empire. Now Jenna Boller shoe salesperson is about to become a shoe-store spy as she…


The Pull of the Moon

By Elizabeth Berg,

Book cover of The Pull of the Moon

Why this book?

When I presented the second draft of the manuscript of my book to my developmental editor, I really thought it was done.

“Nope, not a novel yet. Where’s your inciting incident?”
“What’s an inciting incident?” She explained.
I retorted: “Well, I read this book about a woman who’s just going through menopause, so she goes on a solo road trip. No inciting incident there.”
“What, and you don’t think menopause is an inciting incident?”

And then I re-read Elizabeth Berg’s beautiful story of a long-term marriage; what’s left when child-rearing is done; and what you discover from strangers when you contemplate the second half of your life. Nobody does transitions in women’s lives like Elizabeth Berg; this ended up being my favorite of all her books I’ve read.

The Pull of the Moon

By Elizabeth Berg,

Why should I read it?

1 author picked The Pull of the Moon as one of their favorite books, and they share why you should read it.

What is this book about?

“This is not a novel about a woman leaving home but rather about a human being finding her way back.”—Chicago Tribune

In the middle of her life, Nan decides to leave her husband at home and begin an impromptu trek across the country, carrying with her a turquoise leather journal she intends to fill. The Pull of the Moon is a novel about a woman coming to terms with issues of importance to all women. In her journal, Nan addresses the thorniness—and the allure—of marriage, the sweet ties to children, and the gifts and lessons that come from random encounters…


Anywhere But Here

By Mona Simpson,

Book cover of Anywhere But Here

Why this book?

When this astonishing debut novel about a complicated mother-daughter relationship came out, I wondered if the author had met my mother. Because Adele August believes there’s nothing for her in her small Wisconsin town, she sets off for Los Angeles with her twelve-year-old daughter and a dream—Ann will be a child star; Adele will make a wealthy marriage; they’ll live the lives they were meant to. Simpson’s writing is gorgeous: “My mother and I should have both been girls who stayed out on the porch a little longer than the rest… who strained to hear the long-distance trucks on the highway... girls who looked at the sky and wanted to go away… but who finally sighed, and calling the dog with a mixture of reluctance and relief, shut the door and went home.” Reality can’t live up to Adele’s delusions; mother-child roles are often reversed; but love underlies this tangled mess. And that’s the miracle.

Anywhere But Here

By Mona Simpson,

Why should I read it?

2 authors picked Anywhere But Here as one of their favorite books, and they share why you should read it.

What is this book about?

A national bestseller—adapted into a movie starring Natalie Portman and Susan Sarandon—Anywhere But Here is the heart-rending tale of a mother and daughter. A moving, often comic portrait of wise child Ann August and her mother, Adele, a larger-than-life American dreamer, the novel follows the two women as they travel through the landscape of their often conflicting ambitions. A brilliant exploration of the perennial urge to keep moving, even at the risk of profound disorientation, Anywhere But Here is a story about the things we do for love, and a powerful study of familial bonds.


Boop and Eve's Road Trip

By Mary Helen Sheriff,

Book cover of Boop and Eve's Road Trip

Why this book?

The author had me at the first line: “Boop loved her daughter to the moon and back, but Justine had a way of sucking the joy out of a room faster than a vampire bat.” This road trip story about three generations of women (Boop, her daughter, Justine—who’s not in the car, but her presence isand Justine’s daughter, Eve) set against a background of family secrets, has a decidedly Southern tone. One imagines a narrator relating the story from a rocker on the front porch, a glass of sweet tea in her hand. Although there are lighthearted moments, this is a serious story, about familial expectations, mental illness, family secrets, estrangement, and three women trying to find their way back to themselves and to each other. Travelling with this unforgettable grandmother/granddaughter duo is a gift. 

Boop and Eve's Road Trip

By Mary Helen Sheriff,

Why should I read it?

1 author picked Boop and Eve's Road Trip as one of their favorite books, and they share why you should read it.

What is this book about?

Eve Prince is done-with college, with her mom, with guys, and with her dream of fashion design. But when her best friend goes MIA, Eve must gather together the broken threads of her life in order to search for her.

When Eve's grandmother, Boop, a retiree dripping with Southern charm, finds out about the trip, she-desperate to see her sister, and also hoping to alleviate Eve's growing depression-hijacks her granddaughter's road trip. Boop knows from experience that healing Eve will require more than flirting lessons and a Garlic Festival makeover. Nevertheless, Boop is frustrated when her feeble efforts yield the…


The Bean Trees

By Barbara Kingsolver,

Book cover of The Bean Trees

Why this book?

Whenever I re-read this book, I’m gob-smacked that it’s a debut novel. Taylor Greer just wants to avoid the fate of her peers—unwanted pregnancies and dead-end lives in the small Kentucky town where she was born—when she points her Volkswagen Bug due West in search of something different. She has no idea how different her life will become when she stops at a gas station in Oklahoma and a stranger puts a small child in the passenger seat of her car. The story of how Taylor and the child become a family with the help of some unlikely friends, is one that’s stayed with me from first read. Kingsolver’s writing is quietly and deeply dazzling and paints a stunning picture of what it means to find sanctuary, family, and home in a way you never imagined. 

The Bean Trees

By Barbara Kingsolver,

Why should I read it?

1 author picked The Bean Trees as one of their favorite books, and they share why you should read it.

What is this book about?

The Bean Trees is bestselling author Barbara Kingsolver's first novel, now widely regarded as a modern classic. It is the charming, engrossing tale of rural Kentucky native Taylor Greer, who only wants to get away from her roots and avoid getting pregnant. She succeeds, but inherits a 3-year-old native-American little girl named Turtle along the way, and together, from Oklahoma to Tucson, Arizona, half-Cherokee Taylor and her charge search for a new life in the West.

Written with humour and pathos, this highly praised novel focuses on love and friendship, abandonment and belonging as Taylor, out of money and seemingly…


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