Drawn the Road Again: Chandler O’Leary documents her road trips without a camera or GPS

The artist's new book is a testament to her love of drawing—and the open road

Photo: Chandler O'Leary

Ever since she created her first travel drawing as a teenager, Chandler O’Leary has believed travelers should take time to see as much as they can—and document their road trip experiences as often as they can.

This philosophy was the inspiration behind her new book, The Best Coast: A Road Trip Atlas (Illustrated Adventures Along the West Coast’s Historic Highways), which was released on April 9.

“Look, listen, and learn while you travel, and do your best to take notes and record what you experience,” she says. “In those moments, try to avoid injecting yourself into the experience —your opinions, your background, your biases—there’ll be plenty of time to do that later, when you go back and process what you’ve observed and have used it as inspiration for whatever you might create.”

O’Leary has plenty of experience roadtripping and documenting her travels in the form of drawings and watercolor paintings. Each year she racks up nearly 10,000 miles of road travel. She documents these experiences in her blog, Drawn the Road Again.

The Best Coast book cover.
The Best Coast cover. | Photo: Sasquatch Books

Launched in 2013, the blog has allowed O’Leary to bridge her love of travel, her passion for art, and her desire to pursue a successful full-time independent art career. Drawn the Road Again—which stemmed from an idea given to O’Leary by a friend who saw her sketching during a road trip—is organized thematically rather than chronologically.

“Drawn the Road Again became this repository for my images and essays, where I could draw parallels—no pun intended—between seemingly disparate places and build a bigger picture of America through my drawings and stories,” O’Leary says.

Dozens of paintings piled up on a desk.
Paintings from The Best Coast. | Photo: Chandler O’Leary

Since she started the blog six years ago, O’Leary has dreamed of turning her many travel stories into a book. Then, in 2016, she collaborated with Jessica Spring to produce Dead Feminists: Historic Heroines in Living Color, an artistic celebration of feminists throughout history. This foray into publication inspired her to propose and produce a book of her own.

In The Best Coast, readers travel with O’Leary from San Diego to her current home state of Washington and back again. In between beautiful, hand-painted illustrations are portraits of roadside attractions, hidden histories, and historic highway guides.

“I really wanted to use what I knew about travel and telling stories to create a book from scratch,” she says. “And just like the blog, I wanted to do it entirely with illustration, rather than photography.”

O'Leary holds her painting of a field of flowers in front of the field of flowers itself.
A west coast bloom. | Photo: Chandler O’Leary

The Best Coast is the culmination of two-and-a-half years of research, writing, illustration, and production. But that timeline does not include all the travel that went into the creation of this book, including several West Coast road trips, and all the other travel experiences it took to inspire her artwork over the years. (O’Leary takes about one big road trip of more than 5,000 miles, as well as one or two smaller trips, every year.)

“There isn’t a lot of illustrated nonfiction for adults in general, and really nothing in the way of fully-illustrated travel writing like this.”

The Best Coast differs from most travel books in that it doesn’t include any photographs. O’Leary hopes that the drawings will pull readers in and inspire them to go out and visit the places she’s documented in the book.

“There isn’t a lot of illustrated nonfiction for adults in general, and really nothing in the way of fully-illustrated travel writing like this,” O’Leary says. “I hope that readers and travelers will like it as much as I’ve loved creating it.”

Supporting independent artists

O’Leary has been drawing and painting her entire life. She has a degree in illustration from the Rhode Island School of Design, and she worked as a graphic designer for several years to pay off her student loans. She produced studio work in her off hours, applying for grants, shows, and other opportunities when she had time. But, for a long time, her professional life and her travel art life were separate.

“I have always loved travel, and have been creating travel drawings since I was a teenager, but for many, many years I didn’t feel like it was ‘real’ work, or finished work, or anything like a professional path,” O’Leary says. “So my travel artwork really sort of existed on a parallel plane, all while I was pursuing my professional career as an artist.”

About 11 years ago, O’Leary and her husband moved to Tacoma, Washington, and she used the transition as an opportunity to turn her side business into a full-time gig. Because of the joy she has gotten from pursuing her artistic career and the positive response she’s had from the community around her, O’Leary never looked back.

Chandler O'Leary paints a picture of a lighthouse.
Art in progress. | Photo: Chandler O’Leary.

“My fellow Tacomans have been extremely supportive of my own artistic career—buying my work, attending my shows, spreading the word about what I do, and, most recently, their huge support of my new book,” O’Leary says. “I really owe an enormous amount of my success as an artist and small business owner to my local community, and I hope I can keep paying that forward to my fellow artists and other folks in my town.”

O’Leary believes community building—in one’s hometown, on the road, and through social networks—is one of the best ways for independent artists to find their audience.

“I think the best way that folks can support projects like this and artists like me is by good old-fashioned word-of-mouth,” she says. “Just like the way people share their travel stories with me, it’s been folks sharing my work with their friends and family that has really helped send my work around the world.”

Slowing down, enjoying the journey

O’Leary travels without GPS. She hates turn-by-turn directions, and says it feels like she’s being led around by the nose. She also takes very few photographs during her travels, preferring instead to document each trip in the form of an on-location drawing or watercolor painting. These strategies allow her to slow down, to notice the little details, and to absorb the world around her.

“I have a fear of forgetting, of not noticing the moment properly, of taking life for granted or of missing things as my life moves with and around me,” O’Leary says. “I know it’s not possible to register and capture every single moment of my life, but it seems I’m hell-bent on trying.”

Paintings of maps of West Coast highways.
Paintings of maps. | Photo: Chandler O’Leary

O’Leary, a new mother, is particularly aware of the need to document and remember portions of her life now that she has a newborn baby at home. Though her son is only 3.5 months old, O’Leary is already dreaming of the trips she’ll take with him, through which she hopes he will learn to navigate his way through the world, gain confidence, and carry these stories with him.

For O’Leary, raising her child is similar to taking a new trip. You can plan as much as you want and anticipate what the journey might be like, but some of the best experiences come from stumbling upon surprises and learning along the way.

“I know it’s not possible to register and capture every single moment of my life, but it seems I’m hell-bent on trying.”

“Life and history and culture are ever-changing, ephemeral things. And that’s totally natural—but the pace of change seems to have accelerated in some ways, thanks to technology,” O’Leary says. “I fear we are losing many landmarks, cultural moments, ways of life, and stories without ever examining why—or even noticing that it’s happening until it’s too late.”

Through her art, she is hoping to make a difference—even if it’s on a tiny scale: “If I can get others to stop and notice the world around them—even in what small way I can—I feel that can help us all be more thoughtful, mindful of, and participatory in all this inevitable change.”