The most iconic road trip in the world has to be the USA’s Historic Route 66. The Mother Road originally stretched west from Chicago in Illinois to Santa Monica in California, a 2,448-mile (3,940 km) drive that – if you want to properly savour nostalgic Americana – takes at least a month to complete.
I took on one key section through heartland Missouri to really immerse myself in the history, hanging out in small towns, staying in retro motels and eating in friendly local diners.
It would have been great to have travelled in a turquoise 1966 Ford Thunderbird convertible (echoing Thelma and Louise without the cliff-plunge finale), but a people carrier was more practical.
Paul McCartney and his now wife Nancy Shevell tackled the route in a Ford Bronco in 2008, and were spotted by fans stopping for gas in Saint Louis. That’s where I started my one-week journey, keen to see how the state of Missouri is revving up for the Route 66 (1926-2026) Centennial.
Missourians are busy renovating period advertising displays, polishing their vintage cars and adding new road signs. They also recently welcomed the Ted Lasso film crew who are working on Series 4 of the Apple TV+ comedy-drama.
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Crossing eight states, Route 66 still had dirt trail sections until 1938 when it became fully paved. The highway was shortened and then officially decommissioned in June 1985 to make way for the monotonous Interstate Highway System.
Nevertheless, you can still find long stretches of the original winding road, 317 miles (510 km) of which are in Missouri. Take your time, navigate away from the multi-lane motorways, avoid the fast-food chains and soak up the vibe. It’s not a race, it’s an experience.
Meet me in Saint Louis
This area of the Midwest was once Osage Native American country and early settlers nicknamed Saint Louis Mound City because of the multiple sacred earthwork sites.
The dog-legged 1929 mile-long Old Chain of Rocks Bridge, linking Illinois to Missouri over the Mississippi River rapids, funnelled Route 66 traffic for decades. It’s no longer in general service but has been restored for hiking, biking and reminiscing. I crossed it on foot, on the look-out over the water for American white pelicans fishing for carp.
The Gateway Arch in Saint Louis was erected in the 1960s to commemorate the USA’s pioneers and frontier history. It looks like a stainless steel rainbow, a soaring symbolic curve in the sky, but you can actually travel inside to the top. It’s not for the claustrophobic as the ‘tram’ cabins are tiny but the panoramic view is terrific.
Barbecue is a big deal in Missouri and aficionados know just how they like their spare ribs and tangy sauce – although vegans might like to turn away now.
I lunched at the popular Salt + Smoke BBQ (saltandsmokebbq.com) where they promise to ‘treat your meat right’. A full rack of Saint Louis Cut Ribs is served with beef fat fries, coleslaw and a bacon and cheese popover (like a crispy Yorkshire pudding).
Skipping the chocolate brownie dessert in favour of a visit to the National Museum of Transportation, I saw 1950s crooner Bobby Darin’s one-of-a-kind Dream Car with spectacular rear fins. The bright red chassis has 30 coats of translucent paint with crushed diamond dust for sparkle.
In the collection there are also locomotives, riverboats and other awesome automobiles but Bobby’s 1960 DiDia 150 futuristic design takes the biscuit.
Concrete custard, doughnuts and pancakes
Side Project Brewery (sideprojectbrewing.com) sits directly on Historic Route 66 in the suburb of Maplewood, and its small-batch, barrel-aged beers are renowned. I sampled the luxury Au Revoir brew, with watermelon and sea salt. At £30 for 750mi, it’s almost as pricey as a bottle of champagne but the unusual flavour is undeniably delicious.
The Ted Drewes Frozen Custard stand (teddrewes.com) in Chippewa Street has been refreshing patrons with shakes, ice cream sodas and dense iced ‘concretes’ since 1941. Longevity proves customers love their dairy desserts bucket-size but even the micro portion was more than enough for me.
Alternatively, just down the road, Saint Louis’ Donut Drive-In (donutdrivein.com) started serving up fresh handmade doughnuts to motorists in 1953.
The perfect evening out was a session of 10-pin bowling at Crestwood Bowl on Route 66’s Watson Road. Open since 1958, the contemporary screens with automatic scoring may be digital but the 24-lane alley has much evocative charm, complete with old-school jukebox.
I can’t say I got many strikes but the exercise did me good. After all that sliding and dipping to bowl, my thighs were twanging for days.
All eyes on Eureka
Back on the road, we made a small detour to Laumeier Sculpture Park (laumeiersculpturepark.org) in Sunset Hills. Spread over 105 acres, my favourite exhibit was a giant fibreglass and resin eye, truly disturbing, never-blinking and always alert.
I was ready for brunch at Spencer’s Grill (spencersgrill.com), a traditional Route 66 diner in Kirkwood. Sitting at the counter with a bottomless mug of coffee and a stack of pancakes, I felt like a character in an Edward Hopper painting.
In the joyfully named town of Eureka, we popped into the Visitor Centre of Route 66 State Park, housed is the 1935 former Bridgehead Inn roadhouse (and gambling joint). Free to enter, the place is packed with memorabilia and info about the history of ‘the Main Street of America’.
Missouri is known as the Cave State and has 7,500 geological grottos, full of stalactites and stalagmites. Meramec Caverns (americascave.com) was once mined for saltpeter to use in gunpowder but has long been a tourist attraction.
Local legend linked the caves to bank robber Jesse James and in 1950, ‘Jesse’ was hired to greet visitors – never mind that the outlaw actually died in 1882.
As we headed through the neighbouring towns of Cuba and Fanning, we passed the restored 1938 Wagon Wheel Motel (wagonwheel66cuba.com) which is listed on the National Register of Historic Places, and the jumbo Red Rocker roadside attraction.
This 13-metre high chair isn’t last century but has an authentic Historic Route 66 feel. Small businesses along this bygone cross-country artery erected a whole array of wacky displays to pull in trade.
No such thing as too much neon
Devil's Elbow was a particularly hazardous section of the original rugged road so the Hooker Cut was blasted through a ridge during World War II. The scenic photo-op spot is near to the tongue-in-cheek Uranus Fudge Factory, a bizarre mini shopping complex complete with a Zoltar fortune-telling machine, as featured in Tom Hanks’ film Big.
The newly-opened Route 66 Neon Park, illuminating the night with zinging colours, is just outside pretty Waynesville in Saint Robert. This outdoor display of restored vintage signs from motels, diners and gas stations is a must-see.
The concentration of these stylish and vibrant lights is quite magical and the park has already become a hang-out for teenage couples and excited families.
Camp Joy opened in 1927 on the edge of the town of Lebanon, offering camping pitches for 50 cents. The demand grew and cabins were added for the growing number of Route 66 pilgrims.
The 1946 Munger Moss Motel still stands, with its neon sign glowing, but is currently closed. I could only peer through the windows at the very kitsch original décor.
At the Lebanon Route 66 Museum (lebanon-laclede.lib.mo.us), there are fascinating displays of collectables but best of all, I arrived just time for a car show. In the parking lot, local Lebanon-Laclede County Route 66 Society members had gathered together their vintage vehicles, including a gleaming 1958 Green Dodge truck.
Springfield’s deadly duel
Next stop, Springfield, with nature trails and views of the Ozark Mountains. I was hoping I might bump into Brad Pitt – he went to school here and still regularly visits family. Sadly, the Hollywood star was busy elsewhere.
It was in Springfield that Route 66 was officially named in 1926 (deemed catchier than Route 62).
The Civil Kitchen restaurant (civilkitchen.com) is the perfect place to celebrate Route 66’s inauguration. I can confirm the Devil’s margarita is a rather potent tipple with tequila, lime juice, homemade syrup and a floating top of red wine.
The Bass Pro flagship store, specialising in hunting, fishing and camping supplies, is an extraordinary emporium. There are colossal aquariums, a stuffed grizzly bear killed by bow and arrow and the NRA National Sporting Arms Museum, with engraved Colt revolvers from the Old West.
On Springfield’s town square in 1865, Wild Bill Hickok fatally shot his former friend Davis Tutt with his Colt Navy revolver in a quick draw duel over a gambling debt.
Painted checkerboard red and white in Americana retro style, College Street Café (collegestreetcafe.com) has had various names but has been a Route 66 diner since the early 1950s. The Rolls Royce triple bacon cheeseburger certainly doesn’t need extra sides of deep-fried okra, mushrooms and onion rings but they’re hard to resist.
The History Museum on the Square has a full-scale vintage trolley car and interactive exhibits. One section is devoted to John Steinbeck and his novel Grapes of Wrath, bringing to life the struggles of desperate 1930s Dust Bowl migrants. Limping along Route 66 in their battered trucks, they were searching for a better life on Californian farms during the Great Depression.
Has anyone seen Elvis
Springfield’s elegant Gillioz Theatre (gillioztheatre.com) opened in 1926 and, fortunately, wasn’t knocked down as intended to become a parking lot. It once staged vaudeville acts and screened silent movies with music from a magnificent Wurlitzer organ. The organ may have gone but Gillioz has retained its period décor and now hosts concerts, films and live shows.
Though Elvis Presley never performed here, he did sneak in to relax while on tour in 1956. Manager Colonel Tom Parker couldn’t locate the star and found him watching the Western thriller Jubal.
I sat in Elvis’s seat in the back row of the cinema, connecting with the King of Rock and Roll. That night I also slept in the same motel as Elvis, the Best Western Route 66 Rail Haven (bestwestern.co.uk) – a classic motor court – which opened in Springfield in 1938. Elvis stayed in room 409, now the Elvis Suite, that boasts a pink Cadillac bed.
Just outside town is Gary’s Gay Parita (garysgayparita.com), a photogenic Route 66 shrine which was used in Chappell Roan's Hot To Go! music video. This roadside treasure, which the Hairy Bikers also visited, has a fabulous display based on a 1930s Sinclair gas station, with vintage pumps and vehicles.
Owner Barbara Barns (founder Gary’s daughter) keeps the Route 66 legacy alive, offering warm hospitality with free watermelon for thirsty motorists.
Under restoration close by, the 1927 Spencer Station (spencerstation.myshopify.com) is soon to reopen. Created when Route 66 became aligned with an old stagecoach route, the adjoining garage, barber shop, diner and general store did brisk business with dishevelled and hungry clients until the tiny outpost of Spencer was bypassed in 1961.
Bonnie and Clyde’s Airbnb
Just off of Route 66, Red Oak II is the vision of artist Lowell Davis who bought up buildings from the original, disappearing ghost town of Red Oak to create a whimsical, living community.
Set in a former cornfield, Red Oak II has an old school house, blacksmith and even a cemetery. There’s no charge to enter but be mindful some homes are inhabited and all are privately owned.
Carthage, site of one of the earliest battles in American’s Civil War in 1861, was destroyed by Confederate guerrillas. The town re-emerged from the ruins and the 1890s Jasper County Courthouse was constructed in polished limestone.
The finished building, inspired by European medieval architecture, resembles a castle with turrets, towers and arches, and the exterior was used as the courthouse in comedy film My Cousin Vinny.
Boots Court Motel (bootscourt66.com) was built in 1939 and offers a special step back in time. Legendary actor Clarke Gable was a guest and I was lucky enough to stay in his room with its retro furnishings and antique radio. Be sure to book well ahead as Carthage’s annual festivals fill up hotel beds for miles.
Nearby Joplin hosts the World Street Painting Festival as part of the Route 66 Centennial celebrations. Some 3D designs are already in place in Schifferdecker Park’s outdoor gallery and Downtown Joplin’s Route 66 Mural Park provides some ideal selfie backdrops.
This quiet location made headlines in 1933 when fugitives Bonnie and Clyde were discovered hiding out at a rented Oak Ridge Drive garage flat. The duo and their gang escaped after a violent shootout but left behind a camera and film, with pictures clearly showing their faces. The very same apartment, bullets and all, is now available on Airbnb.
Joplin’s Grand Falls is a broad waterfall, on Shoal Creek, which gushes down a 50-metre wide ledge and is close to the OKKAMO Tri-State Marker, pinpointing the corner where Oklahoma, Kansas and Missouri meet.
In a field just over state lines by the roadside, on Quapaw Nation tribal land, we spotted Frosty, a rare white bison considered a symbol of good fortune. He continued grazing nonchalantly, unaware of his spiritual significance.
Jazz it up in Kansas City
Our last stop, Kansas City, is just north of Historic Route 66, but worth taking in. The Nelson-Atkins Museum of Art has free entry with a world class collection including impressionist paintings and wonderful Japanese woodcuts. The huge quirky shuttlecock sculptures on the lawn outside are a lot of fun.
Billie’s Grocery (billiesgrocery.com) near Union Hill is a heavenly healthy-eating cafe for breakfast or lunch at the end of a cholesterol-heavy road trip. The beet hummus avocado toast is made with sourdough and is topped with a poached egg. Teamed with a mango smoothie, I felt my veins relaxing with pleasure.
The new Museum of BBQ (museumofbbq.co) is the world’s first museum dedicated to the slow and smoky cooking process. A niche activity, here I learnt about seasonings, rubs and everything I could ever possibly want to know about the history of barbecue.
Then it was on to 1887-founded distillery J. Rieger & Co (jriegerco.com) in the Electric Park neighbourhood for a tour and tasting. The whiskey specialists also produce Caffè Amaro, a coffee liqueur blended with botanicals including cardamom and star anise. It goes down very nicely even before sundown.
In the 18th & Vine Historic Jazz District, the Negro Leagues Baseball Museum (nlbm.com) is dedicated to preserving the history of African-American baseball teams, including the legacy of the Kansas City Monarchs.
It was here the Ted Lasso production unit, with Jake Sudeikis, recently filmed for a day. Women’s soccer is big in Missouri and Ted is reported to be coaching a new female football team in the latest storyline.
Housed in the same building, the American Jazz Museum (americanjazzmuseum.org) celebrates the accomplished musicians of the 1920s, 30s and 40s. Certainly a place not to miss.
Kansas City has been designated a UNESCO Creative City of Music, the only one in the USA, recognised for its jazz and swing heritage. “We like to say jazz was born in New Orleans but grew up in Kansas City,” lively guide Debra explained. Saxophonist Charlie Parker was born here and Count Basie joined a Kansas City blues-based orchestra in 1929.
On our last night, we steered ourselves to the Green Lady Lounge (greenladylounge.com) on Grand Avenue for a little live jazz. Open 365 days a year, this laidback and intimate venue is timeless with vintage-style red leather booths and a 1940s baby grand piano. In 1946, the song (Get Your Kicks on) Route 66 was a massive hit for Nat King Cole, who started his career as a jazz pianist. Nat, we did our best.
