Route 66 Road Trip: Must-See Places & The People Behind Them

“So, you two are in Chicago and driving to LA…are you gonna take Route 66?” My dad posed this question and we felt silly that taking the country’s most iconic road trip hadn’t even crossed our minds. We had just hit our 50th state and the Main Street of America was a brilliant homecoming. Zigzagging 2,448 miles across eight states, it’s a highway many of us have driven on–whether we’ve known it or not. It was decommissioned in 1985 and slowly paved over by major interstates or bypassed entirely, putting many of its gems off the beaten track. Though that’s the beauty of the Mother Road, it’s a treasure hunt reserved for those with a sense of adventure and an appreciation for the past. Stay the course and you’ll be rewarded with neon motel signs, classic cars, glass-tank gas pumps, hole-in-the-wall diners, and the wonderful people keeping the spirit of the road alive.

The more we drove, the more 66 piqued our interest. Pulling up to a gas station from the 1920s made us wonder about the first road-trippers rumbling across the nation in Model Ts. A falling down 1950s diner, begged the question, what happened to the classic soda fountain? And a perfectly restored motel adorned with a glowing welcome sign, made us ask..who’s to thank for this? The story of Route 66 is not in its impressive landscapes or even its neon art, but the people who blazed this trail and those who are preserving it.

In this Route 66 travel guide, we’re focusing on the heroes of the road—famous and unsung, past and present—and why they continue to make this highway so legendary. Plus, we’ve added in our must-see places in every state so you can plot your own Route 66 road trip adventure and make some new friends along the way.
 

Chicago Surrounds & The Liquor Store with a Dream

Giddy to start this epic road trip, we drove to the official start of Route 66 in downtown Chicago. In the shadow of a high-rise across from an alley, this small brown road sign with some stickers on it didn’t seem fitting for such a significant landmark. We went deeper into Illinois, scanning the horizon for mid-century diners and drive-ins, but run-down houses and pawn shops seemed to have taken their place. Then in Berwyn, a retro Route 66 sign appeared on a liquor store. We hopped out and took a selfie, then out of nowhere, the owner of Route 66 Beverage came to ask, “Would you guys like me to take one for you?” When he bought the shop 30 years ago, he decided to hang that vintage sign to attract travelers and welcome them to the road. Being on the historic route gave Manny added pride for his shop, though this neglected section of Route 66 needed him just as much.
 

Pontiac, IL & The Original VanLifer

Pontiac was the first town where we felt that 66 magic. It had nostalgic murals painted across the brick buildings, including a map of the entire route with a grey-haired hippie holding a paintbrush. That man was Bob Waldmire. His dad owned the nearby Cozy Dog Diner (home of the original corn dog), and he grew up listening to Route 66ers share stories across the counter. In the summer of 1962 his family took that Cal-i-fornia trip and it would become his first of a hundred. Cruising up and down the route for 40 years and creating art all about it, Bob embodied the freedom, adventure, and wanderlust that lures us all here. We went into the Route Association Hall of Fame and in the center of the room was his home on wheels, a 1972 VW Microbus, decorated with his Mother Road art and keepsakes. The understated museum highlights the incredible entrepreneurs, advocates, and characters along 66–and we quickly realized, the people is what it’s all about.
 

Illinois Route 66 Road Trip Stops

• Take a selfie with Wilmington’s Gemini Giant.
• Relive the opening scene of the Blues Brothers in front of Joliet Prison.
• In Pontiac, pay respects to the road warriors at the Route 66 Association Hall of Fame and gawk at the classic cars of the Pontiac Oakland Auto Museum.
• Belly up to the counter at the Ariston Cafe–one of the oldest continuously operating restaurants on the route (est. 1924).
• Before you hit Missouri, take a walk over the Chain of Rocks Bridge, the engineering marvel that once ushered road trippers across the mighty Mississippi.

Uranus, Missouri & The King of Fart Jokes

We were cruising through Missouri, and Mike says “I think we’re in Uranus.” Then the signs rolled out one after another “We’ll pack your fudge, we’ll grab your nuts, no ifs, ands, or butts…you’ll have fun at the Uranus Fudge Factory and General Store.” Without hesitation, we pulled in and were greeted by a life-size rocket ship, a T-Rex, and the world’s largest belt buckle. Now where to begin? Get freaky at the Uranus Sideshow Museum, throw weapons in the Uranus Axehole, or head to their porcelain throne to read the latest issue of the Uranus Examiner (be sure to pick up a copy, it had us rolling).

We started at the General Store and the shop girls said in chorus, “Welcome to Uranus!” then another guest exited and they all cried out, “Thanks for picking Uranus!” This over-the-top “town” concept was hatched by Louie Keen (now the self-elected mayor) in the early 2000s. He started with Big Louie’s Burlesque Saloon, then added the Chicken Bones Party Bar and tattoo parlor, plus a fudge kitchen until he had an entire strip mall and named it Uranus. He was determined to bring the fun back to Missouri Route 66’s roadside attractions and he succeeded with this gag gift to us all.
 

Missouri Route 66 Road Trip Stops

• Ride the Gateway Arch and gear up with car culture at the National Museum of Transportation in St. Louis.
• Stroll around Cuba, hunting for throwback murals and nibbling on pastries from the Cuba Bakery & Deli Co.
• Catch some Zs at the the 1936 Wagon Wheel Motel or kick off your blue suede shoes with a night in the Elvis Room.
• Get silly in Uranus.

Kansas & The Deli That Won’t Quit

Kansas only has an 11-mile stretch of the Route, but they wear it proudly (particularly with their massive 66 welcome sign made of rusty car wheels). Driving the main street in Galena you feel like you’re on the set of Pixar’s Cars, with good reason. Old-time gas stations have classic Studebakers with twinkling eyes in their windshields and the actual 1951 International Harvester Tow Truck that inspired the Cars character “Mater” lives on in this town.

While Galena plays up its Hollywood side, neighboring Riverton is keeping it real with the help of Nelson’s Old Riverton Store (est. 1925). We pulled up to the brick building, welcomed by a tin “California or Bust” sign and their National Register of Historic Places plaque. Under a hammered tin roof, the narrow aisles were displaying everyday groceries and the deli counter was manned by a silver-haired butcher, Scott Nelson. Something about the rows of salami and bologna kept me from asking about the deli’s vegan options, so I inquired about the history of the store. Scott’s aunt and uncle bought it in the 1970s and hired him when he was 14; when they passed away, they left him the store on the condition that it wouldn’t change. He has honored their wishes, offering travelers and locals alike a hearty slice of the past.
 

Kansas Route 66 Road Trip Stops

• Cruise the nostalgic Main Street of Galena and peek into the old train station
• Rub elbows with stars of Pixar’s Cars at the Kan-o-Tex Station and Radiator Springs
• Stock up on road trip snacks and stories a the Old Riverton Store

Oklahoma & The Father of Route 66

Oklahoma doesn’t get a lot of love as a travel destination, but when it comes to Route 66 the state is the best of the best. Cyrus Avery, the Sooner State’s first highway commissioner and member on the federal planning board for Route 66, was instrumental in creating this national highway (and making sure it stretched the length of his homestate). Many call him the “Father of Route 66.” The Okies pride for the Mother Road runs deep and, with the help of modern-day advocates, this state retains the most drive-able miles of the original alignment of 66. In Miami, Oklahoma, they even have a six-mile stretch of “The Ribbon Road” from the days when the route was only 9-feet wide.
 

The Almost Ghost Town of Erick, Oklahoma
& The Mediocre Music Makers

Driving Route 66 through Illinois, Missouri, Kansas, and Oklahoma, we had seen plenty of picture-perfect Americana towns, but we also saw our share of ghost towns. Many depended on tourism from 66ers and when the road changed course, it left local businesses with little to get by. The only reason we turned on the main street of Erick, OK is because we were gobsmacked by its sheer desolation. Most of the nineteenth-century storefronts with grand display windows were either covered with cobwebs or plywood. Though just when we thought this town had nothing left, we saw the Sandhills Curiosity Shop, shimmering with vintage motor oil and cola signs. We hopped out to take a few pictures, and then the screen door swung open.

“Welcome to the Redneck Capital of the World,” said a guy in denim overalls, gray beard down to his chest, and a few front teeth. “C’mon in!” We entered and it was packed with even more retro signs, auto parts, musical instruments, and photos. This had to be the mother of all Route 66 antique shops—but nothing was for sale. It’s Harley Russell’s personal collection and decor for “The Mediocre Music Makers Studio.” Back in 1999, Harley and his wife Annabelle were in their former health food shop, just messing around on their guitars when a passerby asked if he could bring some people over to listen. They said sure, and a bus-load of foreign tourists walked in. With a mix of being their quirky selves and hamming it up with a little Redneck shock-and-awe, they gave their first performance to Route 66 travelers–of what would become thousands.

Though in 2020, with COVID-19 blocking international travel, Harley barely had any visitors and was looking for a little company. He put a beer in our hands and showed us his late wife Annabelle’s hand-drawn welcome signs, photos of his guests having a raucous time, and gifts from the countless nationalities that visited Sandhills. After an hour of hang-time (laden with his redneck schtick and smack talk), we headed out and noticed one last plaque on the wall, it read “2020 Oklahoma Route 66 Hall of Fame” with the names Harley & Annabelle Russell engraved in gold. We realized we were among a celebrity and that he deserved every bit of his claim to fame.
 

Oklahoma Route 66 Road Trip Stops

• In Miami, pop by the gorgeous Coleman Theater and the Vintage Iron Motorcycle Museum (a must for bikers), then take a bumpy ride down the original Ribbon Road.
• Be totally charmed by the Blue Whale of Catoosa, a 1970s waterpark anchored by an 80-foot-long concrete sperm whale with pectoral fins for slides and tail as a diving board.
• Take a stroll around one of America’s most impressive new city parks, The Gathering Place: Tulsa’s Riverfront Park.
• In Stroud, stop for an All-American breakfast at the Rock Cafe (built from the stone rubble from Route 66’s construction) and plenty more neon photo ops on Main Street.
• Tip your hat to the great entertainer and Route 66 advocate at the Will Rogers Memorial Museum in his hometown of Claremore. (Did you known Route 66 is also called Will Rogers Highway?)
• Choose from 700+ varieties of fizzy drinks at the new-age soda fountain shop Pops Soda Ranch.
  Marvel at the world’s tallest gas pump in Sapulpa (66 feet tall, after the route number).
• For arguably the best overview on the history of the Mother Road, visit Clinton’s Oklahoma Route 66 Museum for a decade-by-decade tutorial with dynamic displays.
• And in the almost ghost town of Erick, say howdy to Harley for us, and see if a copy of Ultimate Journeys for Two is still proudly on display 🙂

Texas & The Roadside Peacemaker

We crossed the Texas state line and hardly knew it with their dinky tin sign. (Isn’t everything bigger in Texas?) The road was largely a lonely stretch of granaries and tumbleweed prairie until about 25 miles east of Amarillo, when the Stoner Patriot Peace Garden of All Faiths emerged out of the dust. Steel signs in rainbow colors, circled around a huge peace sign. Quotes from John Lennon, bible verses, stats about nuclear destruction, and marijuana symbols were cut into the metal and printed in shadows across the ground. Then a headstone of sorts said, “To my family and friends, it’s been a trip & it’s been my honor. Peace. – Richard Daniel Baker, Born June 19th, 1951. Died _____” There is no artist bio or description of any kind at this renegade art installation. When you try to look this guy up, he’s like the enigma of the internet though with some blog digging, I found a friend of Baker’s who added this to the comment thread:

“Richard D Baker is a unique individual whom I have known for 38 years. He is a farmer, a philanthropist and retired telephone repairman. His family has farmed in the panhandle of Texas for over a hundred years. He is a good-hearted man and a good friend to many…When he first conceived the idea, he contacted his dearest friends and asked them to submit a date that was an important in history…it is left to the traveler/visitor to figure out what significance that date represented…After we each painted our pedestal, he threw a huge BBQ with all the fixins for us and many others. That is just his way. Quiet and unassuming and ornery as a little brother.”

You would have thought an artist like Baker would have been shunned as a “dreamer” in the conservative Panhandle, but it turns out…he was not the only one.
 

Texas Route 66 Road Trip Stops

• Go back to the days when gas stations could be Art Deco masterpieces at the Conoco Tower Station in Shamrock.
• Play with optical illusions at the Leaning Tower of Texas.
• Go antiquing in the Route 66 Historic District of Amarillo.
• Grab a can of spray paint and leave your mark at the Cadillac Ranch living art installation.
• Treat yourself to a slice of pie at the Midpoint Cafe, situated exactly 1,139 miles from the start and the finish of Route 66, because as they say on the menu, “When you’re here, you’re halfway there.”

New Mexico & Motel Heroes

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When you’ve been road-tripping for weeks (or 3.5 years) the states can start to blend together, but you always know when you’re in New Mexico, with its rich blend of Native American, Latino, and cowboy cultures. The town of Tucumcari exudes this Land of Enchantment identity with a Route 66 twist, as seen at Tee Pee Curios with its conical facade, the big cement sombrero adorning La Cita restaurant, and the warm neon glow of the Blue Swallow Motel. How could you not stop when its sign pluses “Vacancy” and “100% refrigerated air”?

We got out and Glenn Miller’s Moonlight Sonata filled the courtyard, classic cars peeked out of their private garages, and Schwinn bicycles were ready for a spin around memory lane. A cheery guy in his early 50s came over to greet us. He noticed Buddy the Camper and told us how he and his wife Dawn almost became full-time RVers last year, but decided their next adventure would be to buy the Blue Swallow Motel. Rob and Dawn Federico saw the magic in this place and were humbled by the 82 years of hospitality that preceded them.

While making it slightly more modern and more comfortable, they’ve kept the rotary phones, 1950s Albuquerque furniture, and Lillian Redman’s (the owner for 40 years) Blue Swallow Benediction, wishing travelers to be as “comfortable and happy as if they were in their own home.” The motel was Lillian’s engagement gift in 1958 and she kept the spirit of giving, often accepting barters for hotel rooms for cash-strapped travelers. Chatting with Rob, we could tell he still had a bit of wanderlust, but was comforted by Lillian’s words about her tenure on Route 66: “I end up traveling the highway in my heart with whoever stops here for the night.”
 

New Mexico Route 66 Road Trip Stops

• Go from neon sign to neon sign in charming Tucumcari.
• Take a dip or scuba dive in Santa Rosa’s ancient spring-fed Blue Hole.
• Wander the centuries-old kivas and adobe churches at the Native-American-meets-Spanish-colonial civilization of Pecos National Historic Park.
• Go to Santa Fe’s great convergence of trails—The Camino Real, Old Santa Fe Trail, and the original Route 66.
• When you hit Albuquerque, grab a burger at the nostalgic 66 Diner and catch a show (or a tour) at the 1920s Kimo Theater, a shining example of Pueblo Deco architecture.
• Drive through the flaming 66 sign in Grants.
• Mosey into the El Rancho Hotel, the Gallop lodging of choice to John Wayne, Ronald Reagan, Humphrey Bogart and more old Western stars.

Arizona & An Unlikely Oasis

When Route 66 makes 191 switchback turns up a 3,550 foot mountain, it gets a special name: “Oatman Highway.” Nestled in the Black Mountains, this 48-mile stretch of stark and stunning desert makes you think about how early travelers survived this road. The answer? The Cool Springs Camp and Service Station. It was a place to escape the scorching sun, refuel, hydrate, and rest up before the road got even hairier up Sitgreaves Pass. When the popularity of the route waned in the 1960s, the lights went out at Cool Springs and didn’t come back on until 2004. Route 66 enthusiast Ned Leuchtner restored the main building as a museum, gift shop, and snack bar and partnered with a few vendors to diversify their offerings.

After poking around this throwback oasis, we walked up to the Raw Rock Creations stall, an-open air shop shaded by a tarp and walled in with glass cases. No one was manning the piles of gemstones, until an old guy popped out of a truck with a dusty rucksack. The stall owner Jack Norton was running late after a full morning of rock-hunting the hills. “You gotta see what I just found,” he said to us as he pulled out baseball-sized rocks. He spritzed a stone with water and said, “See those orange veins, that’s fire agate and a good one too.” Mike, as an amateur rockhound, was equally excited as Jack, especially to hear to his tips on finding local gems, rock identification, and his personal story. Jack came to this area just three years ago, but spending his days digging, polishing, creating jewelry, and sharing them with travelers, he found his happy place.
 

Arizona Route 66 Road Trip Stops

• Hike among the ancient trees of Petrified Forest National Park.
• In Holbrook, check into the Wigwam Motel for some 1940s glamping.
• Peek into Meteor Crater, a 550-foot deep abyss and one of the best-preserved meteorite impact sites on the planet.
• Stay up late in Flagstaff to dance the Arizona two-step while drinking 10-cent pints at the historic Museum Club (we went pre-pandemic and had the best time).
• Ride the Grand Canyon Railway from lively Williams to the national park. The Grand Canyon is a fixture on one of our other road trips…read all about it in our National Parks Grand Circle article.
• Poke around the kitschy shops and drive-ins in Seligman.
• Go wild west in the former gold mine town of Oatman, where donkeys roam the streets and cowboy shootouts happen twice daily.

California & Father Knows Best

Having spent the first 18 years of my life in Southern California, so much of this section of the drive was familiar to me—yet I didn’t remember it as Route 66. I knew it as Highway 2 and Santa Monica Boulevard, and even though there were probably a few historic markers, sometimes you just don’t notice what’s so special about your hometown. Sunset was just a couple hours away so were speeding through Rancho Cucamonga, San Dimas, Claremont, and trying to follow a former highway chopped up with hundreds of stoplights and congested intersections. We had to hop on the freeway if we were going to make it to the Santa Monica Pier—the End of the Trail—before dark.

We exited the 10 freeway and the wooden boardwalk, framed with palm trees and a neon archway, welcomed us to the Pacific. We parked Buddy at the beach and walked the final 200 feet of our 2,448-mile journey. We kissed at the “End of the Trail” sign, sealing in our 50-state road trip and the Mother Road that brought us home. My phone buzzed, it was my dad saying he was in the parking lot with a bucket of champagne to toast our journey. After all, it was his idea to take this crazy byway, he raised me a few miles off Route 66, and he’s another one of the people that made this road trip so special.
 

California Route 66 Road Trip Stops

• Get lost in the Joshua tree forest and run down Kelso Sand Dunes of the Mojave Desert.
• Take a slight detour to see the most artful recycling initiative at Elmer’s Bottle Tree Ranch in Oro Grande.
• Stop at the Cucamonga Service Station (est. 1915) for a gas station even older than Route 66.
• Follow in the footsteps of the stars at the Chinese Theater & Hollywood Walk of Fame.
• Stretch your legs one last time at the Beverly Hills Park and some window-shopping on Rodeo Drive.
• Ride the Ferris wheel on the Santa Monica Pier, gaze at the endless ocean and the miles of glorious road that brought you here.

Route 66 Road Trip Tips

• Download the “Route 66 Ultimate Guide”. This app highlights many of the historically significant and charming stops along the route. Unfortunately, their navigation feature is still being developed but by the time you take this trip, it will hopefully be ready to roll! The Route 66 Navigation app already offers this service for $30 bucks, but it may be worth it for how circuitous the route can be.
• Stay on Course. All GPS devices are trying their darndest to pull you off this slow-going byway. Put in frequent waypoints and select “avoid highways” so Google Maps doesn’t try to keep routing you onto the interstate. And keep our eye out for Route 66 signs (some are more subtle than others), they’ll help you stay on track at many intersections.
• Lodging. Try to stay at a few classic motels like the Blue Swallow, Wigwam Motel, etc. RVers won’t have a problem finding boondocking spots along the route with the help of the iOverlander app, friendly businesses, and BLM land. We stayed for free everywhere from the beautiful Coyote Pass Trailhead to Pops Soda Ranch with the purchase of a celery soda and fries.
• Get Smart. School yourself with a stop at either the Arizona Route 66 Museum in Kingman Arizona or the Oklahoma Route 66 Museum in Clinton. Pick up a copy of The Best Hits on Route 66: 100 Essential Stops on the Mother Road. This brand new book informed us on a number of these wonderful people and places.
• Do as Much as You Can. While it’s the sum of the parts that make this road trip so fantastic, if you only focus on a few states, we’d start with the Oklahoma-Arizona section.
• Make Friends: Route 66 may be famous for its classic diners, motels, and gas stations, but for every great place, there are people that made it that way. While it’s tempting to just hop out for a selfie in front of a neon sign, make a point to dig a little deeper and you’ll find the true spirit of the road.