In the summer of 2025 Heather and I drove all 2,400 miles of Route 66, from Chicago to Santa Monica. It took two weeks to get out and one week to get back. Along the way we slept in motels, KOA camper cabins, and the back of the Outback. It was an amazing adventure, and we came home with over a thousand photos and videos.
We shared video from our trip as a day-by-day video series. And we shared our favorite photos in Route 66: Photos from the Mother Road. This post ties the two together: a single timeline of the whole drive, with each day’s story, a link to its video, and a few of the photographs from the road as they fall into place.
We're hitting Route 66 — Chicago to LA — and this is Day Zero. We set up camp near the Indiana Dunes, test out the Subaru camping setup for the first time, and explore the World's Fair Homes before the real journey begins. Two weeks, one car, zero kids, and a whole lot of road ahead.
Day 1 on Route 66 starts in a rainy Chicago and heads southwest through the classic small towns of Illinois. We hit the Gemini Giant in Wilmington, explore the murals of Pontiac, and end the day in Springfield. These little towns are the heart and soul of Route 66.
We leave Illinois behind, passing through the abandoned storefronts of Litchfield and crossing into Missouri at St. Louis. From there it's into the Ozarks — Devils Elbow, Cuba, and all the little stops in between — ending the day at a KOA in Springfield, MO.
Our biggest day yet — three states in one episode. We leave Springfield, MO, dip through the short Kansas stretch of Route 66 at Galena, and spend the rest of the day in Oklahoma. We talk about what makes a great roadside attraction, the future of road trips, and end at the Rock Cafe in Stroud (yes, the one that inspired Cars).
We start the morning making breakfast at camp and then push west through the last of Oklahoma — past Clinton, through the ghost town of Texola, and into the Texas Panhandle. Shamrock, McLean, and Groom bring us the quirky Texas side of Route 66.
We cruise through Amarillo, pass the Route 66 midpoint in Adrian, TX, and cross into New Mexico. The day ends in Tucumcari — neon signs, abandoned motels, and the landscape shifts to wide-open desert. We're officially in the West now.
A shorter day — we detour to Santa Fe for a picnic lunch, try some wild chile-covered Mexican candy, and then head to Albuquerque. The vibe shifts from small-town Route 66 to something more urban. If you're planning this trip, this is the day to plan ahead.
We cross the Continental Divide, hike Red Rock Park near Gallup, and enter Arizona. Petrified Forest National Park, the kitsch of Holbrook, the famous corner in Winslow, and a night in Flagstaff. The scenery gets more dramatic with every mile.
The iconic Arizona stretch — but it's bittersweet. We visit what's left of Twin Arrows (one arrow now, covered in graffiti), cruise through the famous Seligman strip, and stop at Hackberry. This is the stretch that saved Route 66, but some of it is slipping away.
We tackle the dramatic Oatman Highway through Sitgreaves Pass, meet wild donkeys in Oatman, cross into California, and drive through the vast emptiness of the Mojave Desert to Amboy.
We recap the stretch from the Mojave Desert to San Bernardino — sleeping at Roy's in the back of the Subaru, checking out Amboy Crater, stopping by the Baghdad Cafe, exploring the Bottle Tree Ranch, and recovering at the Wigwam Motel with a much-needed pool day. After a night in the desert heat, the Wigwam was exactly what we needed.
The final day. We leave the Wigwam Motel in San Bernardino and drive Route 66 all the way through the suburbs, city streets, and Beverly Hills to the Santa Monica Pier — the end of the Mother Road. We find the End of the Trail sign, walk to Mel's Diner, and take it all in. Two weeks, one car, and 2,400 miles of Route 66 — done.
That’s the whole road. Done in ten quick days. If you want to see our twenty-five favorite photos from the trip, be sure to check out Route 66: Photos from the Mother Road.
