When the federal government decommissioned Route 66 in 1985, many assumed its glory days were over. But decades later, the Mother Road still oozes nostalgia.
WINSLOW, Ariz. — Even after nearly a century, Route 66 still turns a cross-country drive into something unforgettable. America’s most famous highway still knows how to deliver a great story and a fantastic photo op.
When the federal government decommissioned Route 66 in 1985, many assumed its glory days were over. But decades later, the Mother Road still oozes nostalgia. Whether it’s a retro motel, a blue whale grinning from the edge of a pond or a street corner that feels like a song lyric come to life, Route 66 continues to serve a satisfying level of roadside weirdness. These unforgettable stops remind us why Route 66 isn’t just worth the drive – it is the drive.
Lou Mitchell’s
Kick off your adventure with a slice of history and a side of fresh banana pancakes dripping with maple syrup at Lou Mitchell’s. This popular Chicago restaurant has been serving hearty breakfasts since 1923, three years before Route 66 officially opened to travelers. Known as the first stop on the Mother Road, this bustling diner is famous for its fresh-squeezed orange juice and baskets of doughnut holes that somehow vanish before your coffee cools.
Inside, the cozy booths, Formica counters and cheerful servers set the perfect retro tone for the journey ahead. Before hitting the road, don’t forget to swing by the nearby Route 66 Begin sign, just across Michigan Avenue from the Art Institute of Chicago.
Cozy Dog Drive In
Bite into a delicious piece of Route 66 history at Cozy Dog Drive In. Since 1949, this family-owned eatery in Springfield, Ill., has been frying its signature Cozy Dogs, golden cornmeal-battered hot dogs on a stick that helped define a roadside classic. Pair one – or two – with a piping hot cup of chili made from Ed Waldmire’s original 1946 recipe, and you’ve got a bite of history that still hits the spot.
Gateway Arch
As you cross the Mighty Mississippi and cruise into St. Louis, it’s impossible to miss the Gateway Arch, all steel curves and silver shine, pointing you west. Completed in 1965, the Arch honors the pioneers who expanded the United States frontier, and what better place to pause on your westbound Route 66 adventure? It’s the tallest monument in the country, and the short tram ride to the top is as much part of the experience as the view.
Rainbow Bridge
Just outside Riverton, Kan., the curved, white arches of Rainbow Bridge rise like an upside-down smile from the prairie, where it has carried Route 66 travelers over Brush Creek since 1923. Architect James Barney Marsh designed the bridge to be sufficiently strong to support early automobiles but graceful enough to look good doing it. Today, this Kansas state landmark and National Register of Historic Places listing is the last Marsh arch bridge along the Mother Road.
Blue Whale of Catoosa
Built in the early 1970s, this 80-foot-long aquatic oddity began as a surprise anniversary gift from zoologist Hugh S. Davis to his wife, Zelta, who collected whale figurines. It’s hard to miss the bright blue whale grinning from the edge of a pond in Catoosa, Okla. Its cartoon eyes and wide, walk-through mouth practically beg you to stop the car. Made from hand-mixed cement over a metal frame, the whale doubled as a swimming hole for the Davis family and quickly became one of Route 66’s most beloved roadside attractions. While you can’t swim in the pond anymore, you can still climb through its belly and smile back at that goofy grin.
U-Drop Inn Café
As you roll into the Texas Panhandle, fans of the movie “Cars” might recognize the Art Deco U-Drop Inn Café in Shamrock as the inspiration for Ramone’s paint and body shop in Radiator Springs. Built in 1936, it’s trimmed with geometric flourishes and bathed in neon light, giving it a serious retro-cool vibe. Originally home to Tower Station’s gas pumps on one side and the U-Drop Inn Café on the other, the building has been beautifully restored and now serves as a visitor center and museum.
Cadillac Ranch
Just west of Amarillo, a row of 10 classic Cadillacs juts from the earth at a sharp angle, their tail fins slicing into the Texas sky. Buried nose-first in a dusty field since 1974, the San Francisco art collective Ant Farm dreamed up this ever-evolving art installation. Over the years, travelers from around the world have transformed the cars into a graffiti-covered canvas, layering on messages, doodles and declarations in fluorescent bursts and drippy hearts. Bring a can of spray paint and leave your mark. Then, hit the Big Texan Steak Ranch to see if your appetite is as bold as your artwork.
Blue Swallow Motel
In Tucumcari, New Mexico, the Blue Swallow Motel glows like a beacon of mid-century magic on Route 66. Since 1939, this beautifully preserved motor court has welcomed travelers with its glowing neon sign, pink stucco walls and garages adorned with hand-painted murals. But Lillian Redman – who bought the motel in 1958 – gave it heart. She left handwritten notes of kindness in each room, offering weary road trippers more than a place to sleep. Today, it still glows with that same warm hospitality, lovingly preserved by its current owners.
Standin’ on the Corner Park
One of the most photographed spots on Route 66 is a corner in Winslow, Ariz., where the Eagles’ 1972 hit “Take It Easy” comes to life. Fans from around the world stop to snap selfies with a bronze statue of a laid-back guy with a guitar, watching as a girl in a flatbed Ford slows down to take a look at him. Behind him, a two-story mural echoes the lyric with a painted reflection of the truck permanently parked at the curb. A second statue, added in 2016, honors Glenn Frey, co-writer of the song and Eagles co-founder.
Delgadillo’s Snow Cap Drive-In
In Seligman, Ariz., Delgadillo’s Snow Cap Drive-In has been serving burgers and shakes with a side of Dad jokes since 1953. Built by Juan Delgadillo using scrap lumber from the nearby Santa Fe Railway yard, this quirky eatery embodies the playful spirit of Route 66. From the “Sorry, we’re open” sign to a menu that includes a cheeseburger with cheese and a girl cheese sandwich, the Snow Cap is a testament to Juan’s love of humor. Today, his kids keep it going, serving food, wisecracks and Route 66 charm by the spoonful.
Oatman, Arizona
Nestled in Arizona’s Black Mountains, Oatman is your reward for surviving the winding curves of the Oatman Highway. Once a booming gold mining town, it now draws Route 66 travelers with wild burros that roam the streets, descendants of the pack animals miners left behind. Daily mock shootouts add a splash of Wild West theatrics, and the historic Oatman Hotel still claims bragging rights as the honeymoon stop for Clark Gable and Carole Lombard. It’s a little dusty, a little strange and totally unforgettable.
Roy’s Motel and Café
In the ghost town of Amboy, Calif., Roy’s Motel and Café rises from the Mojave Desert. Once a bustling stop on Route 66, its traffic and prosperity vanished nearly overnight when I-40 opened in 1972. Roy’s iconic Googie-style sign still stands tall, thanks to businessman Albert Okura, who bought the town in 2005 with a vision to restore it. Today, under the care of his son, the gas station is back in service, and its neon sign lights up the night once again. It’s eerie, iconic and impossible not to stop for.
Santa Monica Pier
After 2,448 miles of classic motels, colorful murals and quirky roadside attractions, the Santa Monica Pier is the final stop on Route 66. The true terminus sits a few blocks inland at Lincoln and Olympic, but it’s way more satisfying to finish your journey at the edge of the Pacific, with sea breeze in your hair and the End of the Trail sign at your back. The pier also offers classic boardwalk attractions, including a historic carousel, a variety of eateries and an impressive Ferris wheel, all set against the backdrop of the expansive Pacific. It’s a little chaotic, but it is absolutely the right place to end this big road trip.
The end of the road
Route 66 may no longer be the fastest way from Chicago to Los Angeles, but it’s still the most memorable. From neon-lit motels to roadside oddities and dusty desert towns, the Mother Road reminds us that the journey really is the destination.
Sage Scott is a travel writer and photographer who was bitten by the travel bug as a preschooler when her family moved abroad for the first time. She recently checked a classic road trip off her bucket list by driving all 2,448 miles of Route 66, from Chicago to Santa Monica. Follow her adventures at Everyday Wanderer.