Route 66 and the Rise of Roadside America

Barry Bell, our co-founder and resident navigator of nostalgia, can spot a great vintage graphic from a mile marker away. As part of a new series, Barry’s Picks, he will handpick a few images from our archive to give a little history on the era, talk about why he is drawn to it, and share the past’s connection to today. This month, his journey through our collections took him from Los Angeles to Chicago on Route 66.  

History of the Hailed Highway 

When U.S. Highway 66 was created in 1926, it did more than connect Chicago to Los Angeles. It sparked a whole new way of experiencing America. Route 66 provided travelers with access to the wide-open road, giving rise to a distinctive roadside culture. Motels, drive-in restaurants, funky attractions, and neon-lit gas stations popped up along the route, turning an ordinary drive into an automobile adventure. 

By mid-century, “The Main Street of America” had become a cultural icon. Families packed into cars and hit the road for summer vacations. Soldiers returning from World War II drove west in search of new opportunities. Teenagers cruised diners and drive-ins, and roadside billboards promised awesome experiences around every bend. 

That cultural impact was so profound that in 1990, the U.S. Congress passed the Route 66 Study Act, recognizing the highway as “a symbol of the American people’s heritage of travel and their legacy of seeking a better life.” We see that legacy in every color block and halftone screen of the images we preserve and print. 

Our Route 66 collection captures this history in bright, graphic, and nostalgic detail. Vintage postcards, greeting cards, art prints, and magnets celebrate the road itself as much as the destinations along the way.  

Take a trip through time and check out Barry’s Picks on Route 66. 

Pick #1: Map of Route 66 This bright map traces the ride from the Midwest to the West Coast with a banner that proudly states exactly where we got our kicks. It’s the kind of souvenir you could have mailed from a motel lobby after a day of dusty miles and banana crème pie. We print our paper gifts on premium, eco-friendly stock so you can send someone a little slice of the open road. 

Pick #2: Route 66 Decal

With bold type, skyline cameos of Los Angeles and Chicago, and a red ribbon celebrating the highway, this design has a perfect mid-century swagger that’s built for scribbled “wish you were here” notes and retro USPS stamps.  

Pick #3: Here We Are on Route 66

One part map and one part victory lap, this colorful print captures the full sweep of the Mother Road, with vivid vignettes of the landscapes and landmarks you’d pass along the way. Hang it in an office, living room, or studio for a daily dose of go-anywhere optimism. 

Pick #4: Map of Main Street of America   

Enjoy the real-life utility with this snapshot-filled magnet of can’t-miss sights on the highway. Pop this on your fridge to corral lists, postcards, and receipts from your recent travels. It’s a pocket-sized reminder that the next adventure is just one packed bag away. 

See You on the Open Road 

Souvenirs like these weren’t just keepsakes. They were proof you’d been there. The roadside cabins, neon arrows, and giant novelty sculptures that lined 66 became mile markers of memory. Even when Interstates rerouted the flow, the myth of Route 66 only grew stronger and lives on today, almost 100 years (2026 is the Centennial Celebration!) after its inception. 

Ready to get out on the highway and find some adventure? Explore our archive, the Route 66 collection, or start with Barry’s favorites above and build your own roadside gallery.