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Home / Travel

Inside Route 66 highlights: Motels, diners and roadside icons to visit

Marie Barbieri
NZ Herald·
17 Nov, 2025 09:55 PM7 mins to read

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Chicago’s new Route 66 centennial mural. Photo / Marie Barbieri

Chicago’s new Route 66 centennial mural. Photo / Marie Barbieri

Road-tripping 3939km across eight states, Marie Barbieri speed-dates the nostalgia and memorabilia of Route 66.

It’s quirky and flirty, historic and quixotic. It’s a rolling museum of culture, architecture and sculpture. And its locals are unapologetically proud of their eccentric relics. Between the windy city of Chicago and the California dream city of Santa Monica, Route 66 is a showreel of vintage vibes.

Illinois

From the historic BEGIN sign in downtown Chicago, I head for Old Joliet Prison. Reaching East Gate, where Elwood met Joliet Jake in The Blues Brothers, there’s a crowd. But songs and selfies soon fade. Touring the haunting hallways between the inmate-constructed Gothic Revival walls, cells stand peeling.

At Dwight, I pull into flowerbox-windowed Ambler’s Texaco Gas Station. As if a pop-up storybook, the restored fuel-stop houses a 1914 Model-T fire truck. Today, vintage bowsers befriend EV charge points.

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 Old Joliet Prison’s Blues Brothers sculpture. Photo / Marie Barbieri
Old Joliet Prison’s Blues Brothers sculpture. Photo / Marie Barbieri

At Carpenter Park in Springfield, a section of historic Route 66 lay buried beneath soil for 90 years. Unearthed like a time capsule, it opened to the public in July 2025. Where wayside signs were once torn down, interpretive centennial plaques (for November 2026) celebrate this now pedestrianised patch of reincarnated road.

It’s neon signs galore at Motorheads bar/diner/museum. Racing cars hang from ceilings and beer taps crown vintage car rears. Owner Ron Metzger polishes his 1950 Mercury Coupe beside his 9m fibreglass statue holding the world’s largest Route 66 shield. It’s Americana-central, here.

 Chicago’s historic Route 66 start point. Photo / Marie Barbieri
Chicago’s historic Route 66 start point. Photo / Marie Barbieri

Missouri

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Crossing the border into St Louis, I walk across the 36.8-ha Gateway Arch National Park: the country’s smallest. It flaunts a towering 192 metre tall stainless-steel arch. After admiring native plants documented by the Lewis and Clark Expedition, I circle the tree-lined reflection ponds as the Mississippi flows by.

 Leaving your mark at Cadillac Ranch. Photo / Marie Barbieri
Leaving your mark at Cadillac Ranch. Photo / Marie Barbieri

I reach (the other) Springfield, in Missouri. It’s the official birthplace of Route 66, where officials first proposed its name in 1926. And it’s wallpapered in murals. One by GPA Jankins paints a vivid canvas of cars. Nearby, the Route 66 Car Museum further showcases classic and vintage rarities, to include a 1926 Ford Frontenac, a 1907 REO Runabout and a 1947 Diamond T.

Tonight, I share a room with Elvis. However, he’s already left the building. Said to have had a fall-out with his group in 1956, Elvis checked into 1838-built Rail Haven Motel as his mother was staying here. Climbing into a pink Cadillac bed in the Elvis Suite gives me a buzz.

 Gateway Arch National Park’s reflection ponds. Photo / Marie Barbieri
Gateway Arch National Park’s reflection ponds. Photo / Marie Barbieri

Kansas

Kansas captures just 20.9km of Route 66. But its historic byway passes through Galena, where I find 1934 Kan-O-Tex Service Station. It’s where John Lasseter found inspiration for Tow Mater in the Disney movie, Cars, thanks to a hoopty he spotted here.

Oklahoma

Reaching the Tulsa Market District, a smorgasbord of flavours draws me into Mother Road Market. Mexican tacos tempt. But I can’t resist the Chakra Chana chickpea curry from Bhodi’s Bowl.

Musical history at the Tulsa Arts District, leads me to the Bob Dylan Center, a museum filled with handwritten manuscripts and stirring imagery.

Oklahoma epitomises the Old West, where cattlemen buy their authentic gear at Stockyards City, also home to Oklahoma National Stockyards. I leave with neither cow nor cowboy, but cowboy boots to boot. Yeehaw!

 Tulsa Arts District, home to the Bob Dylan Center. Photo / Marie Barbieri
Tulsa Arts District, home to the Bob Dylan Center. Photo / Marie Barbieri

Texas

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On the Texas Panhandle, I explore the 20.9-ha Palo Duro Canyon State Park. Its mesh of hiking trails, hoodoos and caves is home to the canyon wall-dwelling Palo Duro mouse. Horse-riders track the canyon’s softer slopes while mountain-bikers tackle the tougher terrain.

Psychedelic Cadillac Ranch near Amarillo is a ‘Car Henge’ of 10 Cadillacs face-planted in the ground. A trailer sells fluoro spray paints for visitors to (legally) graffiti the bums-up car ghosts.

 Palo Duro Canyon’s nature trails. Photo / Marie Barbieri
Palo Duro Canyon’s nature trails. Photo / Marie Barbieri

I consider myself a good secret keeper but can’t help revealing the speakeasy hidden beneath The Barfield Hotel. After checking in, I head to the basement and behind a clandestine bookshelf appears Paramount Recreation Club. Sipping a Bee’s Knees, the barman tells me that the illicit club was created by Oliver-Eakle, a female prohibitionist! Oh, to have been a 1920s gossip!

New Mexico

From New Mexico’s high desert appears Blue Hole, and my bikini. At Santa Rosa, I slip into its glass-clear artesian spring, glinting like a sapphire ring. Today’s 15C perks my pointy bits and earns a scream. Through its crystalline 30m depth, I spot brave divers gazing into submerged caves.

 Blue Swallow Motel’s historic sign. Photo / Marie Barbieri
Blue Swallow Motel’s historic sign. Photo / Marie Barbieri

A blue neon sign glows seductively above Blue Swallow Motel in Tucumcari. Mural-painted car ports shoulder vintage rooms ornamented with 1940s decor. Back in the day, the owners apparently accepted belongings for payment from cash-strapped travellers. Nice.

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 The crisp artesian spring at Blue Hole, New Mexico. Photo / Marie Barbieri
The crisp artesian spring at Blue Hole, New Mexico. Photo / Marie Barbieri

Arizona

Today is devoted to Petrified Forest National Park, a world of Triassic fossils, mesas and petroglyphs. Painted Desert’s striated bands are dizzyingly alluring. But the 200-million-year-old petrified logs blow my mind. Silica, quartz and amethyst deposited into the fallen trunks later crystallised, preserving them into rainbowed stone.

Holbrook is home to 1950s-esque Wigwam Motel. Its 15 concrete tipis are softened with hickory log furniture. They are fronted not by flowerbeds, but a topiary of vintage cars.

 Taking it easy in Winslow, Arizona. Photo / Marie Barbieri
Taking it easy in Winslow, Arizona. Photo / Marie Barbieri

At Standin’ on the Corner Park in Winslow, I nudge up to a statue of singer/songwriter, Glenn Frey, who stands before the famous Flatbed Ford girl so famously lyricised in the 1972 classic, Take it Easy by The Eagles.

With music now on my mind, I pull into The Museum Club in Flagstaff. On go the cowboy boots as it’s line-dancing night. Built in 1931 by a taxidermist, I boot-scoot along the dance floor of this rustic ponderosa-pine log-stacked cabin. I leave with country music twanging through my veins.

Bed tonight is a silver cylinder. Kingman’s Tin Can Alley on 66 sports swanky brand-new Airstreams. Each named after a Route 66 town, I’m in Hackberry. And it’s just steps away from dinner at Mr D’z Route 66 Diner and Mudd on 66 Coffee Shop.

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California

At Elmer’s Bottle Tree Ranch, I hike through a forest of glass. Elmer Long scavenged for bottles throughout life, which grew into this sun-glinted offbeat installation. Each “tree” is surrounded by dilapidated railroad signs, sewing machines, cash registers and typewriters rusting in peace. The unconventional artist, known far and wide to have a heart of gold, passed on in 2019.

 Still-operating Fair Oaks Pharmacy in Pasadena. Photo / Marie Barbieri
Still-operating Fair Oaks Pharmacy in Pasadena. Photo / Marie Barbieri

In Pasadena, I prop up the bar at Fair Oaks Pharmacy, before its old-time phosphate soda fountain. 100 years on, the pharmacy continues to compound remedies and houses an impressive collection of old-time dolls and boardgames.

Dining at True Food Kitchen confirms I love LA living. Anti-inflammatory dishes curated by Dr Andrew Weil are science-based, designed to nurture both the body and the planet.

On the final morning of my journey, my excitement revs up a gear when the Pacific rolls in. Celebrating on Santa Monica Pier, I mount a historic wooden horse on the century-old merry-go-round, then the solar-powered Ferris wheel. A display shares the story of Will Rogers, the comedian/actor who originally inspired Americans to travel Route 66.

 The end of Route 66. Photo / Marie Barbieri
The end of Route 66. Photo / Marie Barbieri

I reward myself at the coastal chic Shutters on the Beach. There, I dine on fresh seabass at Coast Beach Cafe and digest my epic pilgrimage across America. It’s then a little emotional as I swing open the shuttered doors of my beachfront room. Balcony-perched, I smile as LA’s iconic skaters and bike-riders wheel by.

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Crocheted by historic byways and modern highways, storied Route 66 remains tightly stitched through the backcloth of the USA.

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