ROUTE Magazine didn’t exist in 2015 when editor-in-chief Brennen Matthews, his wife Kate, and their young son, Thembi, left their home in Kenya for Toronto, in search of a fresh start. Matthews, a Kenyan native who also holds a Canadian passport, had just turned 40 and was ready for new challenges—both professionally and personally. The couple was about to celebrate their 17th wedding anniversary and Thembi was 8 years old when Kate suggested the family take to the road. “I think we should do a road trip to clear our heads and open our hearts a bit,” Matthews recalls her saying.
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Kate wanted to go to California and after researching potential routes, only one seemed to offer the quintessential American experience they were seeking: Route 66. The family knew little about the iconic cross-country highway beyond what they’d seen in Pixar’s Cars and other pop-culture touchstones. “The more we read, the more we fell in love with the history, the wacky roadside attractions, the neon, the restored petrol stations, and the people and their stories behind the route,” says Matthews.
Despite describing themselves as “story-driven people,” Matthews insists he had zero intentions of writing a book from their first 2-month trip, which took them from the start of Route 66 in Illinois to the Santa Monica Pier and back again. “We took our time, talked to people the whole way, got their stories, and got a strong sense of Middle America—it was fascinating and really impacted our lives.” The resulting travelogue, Miles to Go: An African Family in Search of America Along Route 66, was published in 2022 by the University of New Mexico Press.
As an editor and writer who launched Destination Magazine while living in Nairobi, Matthews says it’s in his nature to take a lot of notes; he carries a small tape recorder with him on his travels, and eventually realized he wanted to share the transformative trip with others. “The book kind of wrote itself as we went,” Matthew says.
While writers and roadtrippers may understand the modesty in Matthews’ remark, books don’t write themselves without countless hours of research, experience, and passion for their subject matter, any more than road trips happen without someone capable behind the wheel—or in the passenger seat. “Kate is a great navigator,” he says. “We didn’t get lost too many times, but when we hit dead ends or closed roads, we chose not to be frustrated by it. It’s part of the coolness of vintage America, part of the history—sometimes the road just ends and we had fun retracing our steps.”
Despite growing up in Africa, where Matthews says it’s more common to go directly from point A to point B in a Land Cruiser or Range Rover, a love of the open road courses through his family. Thembi, who has been taking trips with his parents since he was a baby, loves roadside giants, neon, and quirky characters. “He still talks about people we met on the road on our very first trip—he’s a real roadtripper, it’s in his soul,” Matthews says.
The opportunities for road travel are limited in the family’s home base of Toronto, but they find a way to scratch the itch whenever possible: “When you’re in America, you can hop in your car and drive to cool places an hour or two away,” Matthews says. “We’ll drive an hour to get ice cream just to be in the car—with the music playing, windows down, and open road ahead of us, it just sets your mood right.”
Motels and muffler men
The family’s first-ever Route 66 stop was at the Launching Pad Drive-In in Wilmington, Illinois, home to the 21-foot-tall Gemini Giant muffler man. Matthews writes: “There was something distinctive, human even, about this enormous relic from a bygone era that moved us … the beginning of a road trip—especially on a legendary route like 66, which has been touted for decades as the most famous road in America—held something tantalizing and magical for me and for my family.”
Since their first trip, the family has traversed the entirety of Route 66 10 times. They travel in a Volkswagen SUV and try to stay in iconic roadside motels when possible. Matthews says he understands that not everyone is able to spend months on the road, but cautions travelers not to rush through the route’s first four states: Illinois, Missouri, Kansas, and Oklahoma. “If you want some of the best classic neon, sleep in Missouri for a few nights,” Matthews says, recommending Show Me State offerings such as the Wagon Wheel Motel in Cuba, Boots Court in Carthage, and Best Western Route 66 Rail Haven in Springfield.
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The family also stayed in the recently-restored La Posada in Winslow, Arizona; La Fonda On the Plaza in Santa Fe, New Mexico; and the Blue Swallow in Tucumcari, New Mexico; all of which he recommends visitors book well in advance. But if you have to wing it, that’s OK too: “We stayed in some dodgy places that looked a bit like a crime scene, but that was an interesting experience too,” Matthews says. “Sometimes the very best stories come out of the worst experiences—as long as you survive, you’ll get a great story out of it.”
Miles to Go is as packed with real-life characters and their stories as the family’s SUV was with souvenirs when they returned to Toronto. While they’ve had their fair share of mishaps and unexpected detours, their experiences traversing the U.S. have been overwhelmingly positive. The mixed-race couple (Matthews is white and his wife is Black) understands that the U.S. “is a complicated country when it comes to race,” and Matthews is frequently asked if they encounter racism out on the road. “We’d say the opposite,” he says.
“Americans tend to be very curious and gregarious, so we did notice a lot of people just staring at us. But the person usually doesn’t care that we’re Black and white, they’re just curious, wondering, ‘Who are these people? Why are they here, what are they doing on Route 66?’ The curiosity is endearing—there’s something sweet about them having an interest in your story and how it connects to their story.”
When it comes to sharing and collecting stories, Matthews found that most of the people they met seemed eager for connection, and, perhaps especially, to share their love of Route 66 with similarly-inclined travelers. “Americans love talking about themselves, which is great because we love hearing their stories,” Matthews says. “Don’t be afraid to talk to people and connect with them as you go—if you’re curious, just ask a question.”
One question Matthews and his family might never get tired of asking is “Where should we go next?” He says no matter how many times they travel Route 66, the family looks forward to reconnecting with old friends just as much as seeing new development and historic attractions refurbished by new generations. In addition to Miles to Go (Matthews’ first book), the trip inspired the launch of ROUTE, a bi-monthly print publication highlighting the people and places that continue to draw travelers to the Mother Road in search of their own answers.
After thousands of miles on the road, Matthews writes: “Now I can say that we have ventured down America’s Main Street and fallen in love with an endangered way of life, as well as a history that still entrances people from across the globe … We may not know for certain what tomorrow holds, but without a doubt, our time on Route 66 in the warm embrace of Middle America gave us the support and space we needed to find some of the answers we were looking for.”