Oklahoma City opens the route in a capital shaped by cattle, oil and the highway itself, one of the original stops along Route 66’s 1926 alignment. Just east of downtown in Arcadia, the Arcadia Round Barn has stood since 1898, its curved wood-plank interior a rare feat of construction and one of the most photographed stops on this stretch of the Mother Road. A few minutes down the highway, Seaba Station Motorcycle Museum fills a restored 1921 service station with an impressive collection of vintage and rare bikes. Back in the city, break for lunch at FLINT Restaurant & Bar before browsing antiques, local goods and art at the OKC Farmers Public Market, housed in a 1928 building that has anchored the neighborhood for nearly a century. As the day winds down, head to Uptown 23rd District, where cute boutiques and bright murals set the scene for dinner at Red PrimeSteak downtown.

Amarillo is a cattle-ranching hub known for its Old West heritage, wide-open plains and no shortage of larger-than-life roadside attractions. Just west of downtown, Cadillac Ranch’s 10 nose-down, graffiti-covered Cadillacs have invited visitors to leave their mark with a can of spray paint since 1974. From there, settle in for lunch at the Big Texan Steak Ranch, an Old West-style dining hall home to a free 72-ounce steak challenge — finish the massive steak and all its tasty sides within 60 minutes, seated the whole time, and the meal is on the house. Continue west on old Route 66 toward Adrian, Texas, for a side trip to the Midpoint Cafe, the official halfway point of the historic highway, equidistant from Chicago, Illinois, and Santa Monica, California, in either direction. Pull up a stool for a slice of the cafe’s famous “ugly pie” and a quiet coffee break before heading back into the city. As evening falls, settle in for dinner at Cellar55, a downtown wine bar and restaurant built into a converted historic building, before tucking in for the night.

Start the day at the Tucumcari Historical Museum, tracing the area’s ranching, railroad and Route 66 history through a massive collection of artifacts and vintage vehicles. Break for lunch at SideKix on 66 or La Cita Restaurant, both local institutions serving green chile and diner classics beneath their own nostalgic roadside signage. Spend the afternoon browsing Tee Pee Curios, a trading post stocked with souvenirs dating back to the 1940s, then wander downtown to spot murals. As the sun sets, cruise Tucumcari’s Neon Motel Row, where a string of restored vintage signs flicker to life — the Blue Swallow Motel’s sign is among the most photographed on the entire route. Cap the night with dinner at Del’s Restaurant, easy to spot by its landmark steer sign out front.

Santa Fe closes out the route with millennia of history and a jolt of contemporary art. Start at Santa Fe Plaza, the city’s adobe-lined historic heart dating to 1610, ringed by shops, museums and the Palace of the Governors. Break for lunch at The Shed, tucked into a 1692 hacienda just off the plaza and known for its flavorful red and green chile since 1953. Spend the afternoon at Meow Wolf, an immersive art installation housed inside a converted bowling alley, where visitors wander through a surreal, interactive maze built by hundreds of local artists. Wind down with an evening stroll through the Canyon Road Gallery District, where more than 100 galleries line a single historic street, many housed in converted adobe homes. Finish the trip with dinner at Geronimo, a fine-dining destination on Canyon Road serving contemporary Southwestern cuisine inside an 18th-century adobe building. From here, it’s a short drive to Albuquerque International Sunport (ABQ) for a flight home, or continue the adventure by picking up Route 66 westbound toward Arizona and California.