For a century, drivers have hit the open road chasing the American Dream along Route 66, the legendary highway that originally stretched about 2,400 miles from Chicago to Los Angeles. Established on November 11, 1926, Route 66 forever changed how Americans travel and became a symbol of freedom and adventure. New stamps from the U.S. Postal Service celebrate the 100th anniversary of the iconic road, honoring its enduring spirit and the ongoing efforts to preserve this uniquely American treasure.

Art director Greg Breeding says the scope of the project was “daunting” at first, once but once our researchers located David Schwartz, a Route 66 photographer with over 20 years of photographing the road, the process became much smoother. Schwartz became the resource for acquiring images for the stamps, while teaching Breeding some Route 66 history and lore.

“Not only is David a seasoned expert of Route 66, but he also happens to be a very fine photographer,” Breeding says. “I personally liked what some call the 'editorial' feel of his work. That is, it does not appear commercial or slick but has almost a photojournalistic quality.”

Schwartz became interested in the road in 1988 after hearing Depeche Mode’s cover of the song “(Get Your Kicks on) Route 66.” He says he used to listen to it and dream of the adventures it held. He made his first trip in 2004 and has since driven it 40 more times.

“Only once did I make the full trip from Chicago to Los Angeles in one go,” Schwartz says. “As a photographer, I found it’s far more meaningful, rewarding, and enjoyable to focus on smaller sections — allowing for deeper dives into the towns, people, and landscapes along the way.”

When Schwartz is taking photographs on the road, he says he looks for moments that feel real and tell a story or capture a mood.

“I pay close attention to light, especially at sunrise or sunset, because it can completely transform a scene,” he says. “I’m drawn to how places change over time — what’s still standing, what’s faded, and what’s been brought back to life.”

As Route 66 celebrates its 100th anniversary, Schwartz notes it’s so much more than simply a road.

“Route 66 is a thread that weaves together American history, culture, and identity,” Schwartz says. “It tells the story of how people moved, adapted, and built communities. Driving it today connects you to that story in a real, tangible way.”

Having his work featured on stamps is a dream come true for Schwartz, and he hopes they will inspire others to seek their own adventures on the road.

“The thought that someone might see one of these images and feel that same spark I felt years ago — that’s everything to me.”

Now on sale! The 2026 Stamp Yearbook