US road trip: a guide to Route 66
Route 66 is the quintessential American road trip. No other road has captured the imagination and the essence of the American spirit. It has inspired musicians, filmmakers and writers, from classic literature (John Steinbeck’s The Grapes of Wrath) to Pixar movie Cars and video game Grand Theft Auto. The highway’s soundtrack, (Get Your Kicks on) Route 66, written in 1946 by Bobby Troup and first recorded by Nat King Cole, has been covered by more than 50 musicians, from Aerosmith to the UK Subs.
Route 66 was the first highway of its kind. In 1926, the 2,448-mile road was designed to be the first trans-continental, year-round highway. It connected urban and rural America from Chicago to Los Angeles, crossing eight states and three time zones. Like an artery, the “mother road” nurtured communities and serviced millions of truckers and road trippers for decades. Families who were forced to leave their homes during the Great Depression and the Dust Bowl, with few resources and a little hope, motored west on Route 66 in search of a better life. This “road of dreams”, symbolising a pathway to easier times, was one of the only US highways to be laid out diagonally. It cut across the country like a shortcut to freedom.
Route 66 grew in popularity in the 50s, when vacationers loaded up their Airstreams and hit the road to see mom-and-pop trading posts, teepee motels and reptile farms. But Dwight Eisenhower’s 1956 Federal Highway Act changed everything. The bigger, newer and faster four-lane interstate system bypassed Route 66 and was the beginning of its demise. Businesses shut, towns suffered from loss of tourism and parts of the route were abandoned altogether. By 1985, Route 66 was decommissioned and officially ceased to exist.
Only 85% of the road has survived, but its spirit lives on. In the past decade, non-profit organisations and the US National Park Service have mobilised efforts and provided grants to protect and preserve what is left. Life is percolating through Route 66 once again, and people come from all over the world to get their “kicks”. Car enthusiasts ship their classic Mustangs, Fords and Chevys across oceans to cruise this iconic road and experience a true slice of Americana. The cycle of struggle, triumph, survival and nostalgia is laid out around every bend. Today, road trippers will see vintage motels, old-school diners, restored gas stations and towns that look frozen in time. It’s the trip of a lifetime.

Classic places to stay for under $150 a night
1 Three Roses Bed & Breakfast, Pontiac, Illinois

This beautiful house, built in about 1890, has a lovely front porch, charming rooms, comfy beds and warm hospitality. Owner Sharon Hanson has two mottos: “Do unto others as you would have them do unto you” and “Always give the customer more than they pay for”. She also makes a fabulous breakfast. Guests can choose from pancakes, eggs Benedict, homemade granola, fresh cinnamon rolls, sausage, “biscuits”, hash browns and scones. Everything is cooked from scratch and absolutely delicious.
Doubles from $129.95 B&B, +1 815 844 3404, threeroses.us
2 Campbell Hotel, Tulsa, Oklahoma

For modern-day comfort in a classic, historic setting, try the beautifully restored Campbell Hotel in midtown Tulsa. Built in 1927, it spans an entire block, with 26 themed rooms, including one inspired by the Rat Pack, and the ultimate Route 66 suite, complete with vintage road signs. The attached Maxwell Restaurant does delicious dinners, and spa services are available on site. What could be better after a long day on the road?
Doubles from $139, +1 855 744 5500, thecampbellhotel.com
3 Blue Swallow Motel, Tucumcari, New Mexico

Driving up to the Blue Swallow feels like stepping back in time. It’s been in business since 1939 and it’s on the National Register of Historic Places. Most of the rooms have 1950s furniture, chenille bedspreads, art deco touches and old-fashioned telephones. A classic car is parked outside, by the vintage lawn furniture, and it has one of the best neon signs on Route 66.
Doubles from $79.95, +1 575 461 9849, blueswallowmotel.com
4 La Posada Hotel & Gardens, Winslow, Arizona

For an unforgettable experience, stay at La Posada, a stunning Spanish colonial building designed by Mary Colter for the Fred Harvey Company in 1929. Its 84 Harvey Houses were the first restaurant chain in America, supplying quality food at reasonable prices in clean, elegant restaurants to passengers on the Santa Fe Railway. Even if you can’t stay the night, buy the $3 walking tour book at the gift shop and stroll around the art gallery and flower gardens, see the world’s largest Navajo rug, and browse the gift shop selling Fred Harvey jewellery, kachina dolls, textiles, metalwork and pottery. Its award-winning Turquoise Room Restaurant serves authentic south-western cuisine. The entire property is an absolute treasure. There’s a new documentary on the Harvey House waitresses who made them famous, called The Harvey Girls: Opportunity Bound.
Doubles from $119, +1 928 289 4366, laposada.org
5 The Wigwam Motel, San Bernardino, California

The Wigwam is the epitome of kitsch. These distinctive and historic concrete hotel rooms were built in 1949 in the shape of 20ft-tall teepees. Operator Kumar Patel has spent more than $500,000 renovating the property, and it shows. The teepees are comfortable, cosy and immaculate, with TVs, free Wi-Fi and a mini fridge. There is also a garden with palm trees, a fire pit, a swimming pool, classic cars and a gift shop. Americana at its best.
Doubles from $73, +1 909 875 3005, wigwammotel.com
Great diners
6 Lou Mitchell’s, Chicago, Illinois

Lou Mitchell’s has been a time-honoured stopover and Chicago institution for more than 90 years. This street, Jackson Boulevard, was the original starting point for Route 66 in 1926, and Lou Mitchell’s has been serving fantastic food in generous portions here ever since. If there’s a queue, join it. They give out free sugar-dusted doughnut holes while you wait. There’s also a free box of Milk Duds (chocolate caramels) at your table and Route 66 memorabilia on the wall. Open for breakfast and lunch only.
Meals $8-$15, 565 West Jackson Boulevard, +1 312 939 3111, loumitchellsrestaurant.com
7 The Ariston Cafe, Litchfield, Illinois

The Ariston has been run by the Adam family for more than 90 years and is one of the oldest restaurants on Route 66. Last October, the owner put the Ariston up for sale and they are taking their time to find the right buyer – someone who will provide the same quality food and service. In case they don’t manage that, go there now and experience one of the finest classic diners on Route 66. It has a wide-ranging menu of home-cooked food, from prime rib to tasty patty melts. And leave room for dessert: it does the best red velvet cake in the world.
Meals $7-$24, 413 Old Route 66 North, +1 217 324 2023, ariston-cafe.com
8 Carl’s Drive-In, Brentwood, Missouri
For mouth-watering burgers and old-school service, grab a seat at the 16-stool counter at Carl’s Drive-In. The restaurant was built on the remains of a 1920s gas station and has been a local institution for over 70 years. It specialises in thin yet juicy crispy-edged burgers with tons of flavour; and the ice-cold creamy root beer, served in frosty mugs, is made daily from a recipe dating back to 1919.
Meals $2.50-$6, 9033 Manchester Road, +1 314 961 9652, no website
9 Tia Sophia’s, Santa Fe, New Mexico
For great authentic New Mexican food and the best green chilli in Santa Fe, Tia Sophia’s will not disappoint. It’s a true locals’ hangout, with friendly service and delicious fare, smothered with homemade chilli and served with flaky sopaipillas (fried pastries). If you can’t decide between green or red chilli, just say “Christmas” and you’ll get both! (Wouldn’t it be great if this always happened?) If there’s a queue, don’t fret: it usually moves quickly and it’s definitely worth the wait. Breakfast and lunch only.
Meals $6-$12, 210 West San Francisco Street, +1 505 983 9880, no website
10 Emma Jean’s Holland Burger, Victorville, California

Emma Jean’s is the classic Route 66 diner experience. It specialises in extra-thick towering milkshakes, crispy chicken-fried steak and juicy burgers. The Brian burger is a favourite – Ortega chilli and Swiss cheese in thick parmesan-crusted garlic bread. The portions are huge, so split a sandwich or leave your diet outside where it belongs. This is the diner that Uma Thurman walks into after having been buried alive in Quentin Tarantino’s Kill Bill 2. Cash only.
Meals $5-$11, 17143 D Street, + 1 760 243 9938, no website
Great bars
11 The Green Mill Cocktail Lounge, Chicago
The Green Mill is the place for late-night jazz and cocktails. It has hosted jazz greats since 1907. In the 1920s, it was a mob hangout and Al Capone preferred the booth near the curve of the bar. With art deco decor, it still has that sophisticated speakeasy vibe. It also hosts one of the longest-running poetry slams in the country. It is in Chicago’s Uptown neighbourhood (about 20 minutes from Route 66) and worth the detour. It has a free parking lot reserved for customers from 6pm-6am one block west at Lawrence & Magnolia Street.
4802 North Broadway, +1 773 878 5552, greenmilljazz.com
12 Hotel Monte Vista Cocktail Lounge, Flagstaff, Arizona

This place was built in 1926, the year Route 66 opened. It’s attached to the historic Monte Vista hotel, which exists thanks to local residents raising over $200,000 to build it. The Lounge was a speakeasy in the 1920s and hosted Humphrey Bogart, Carol Lombard, Gary Cooper, John Wayne and Clark Gable. John Wayne allegedly got so drunk here he tried to take his horse into the lift. It’s also rumoured to be haunted, with moving bar stools and ghosts that dance. Good times.
100 North San Francisco Street, +1 928 779 6971, hotelmontevista.com
13 The Museum Club, Flagstaff, Arizona
This log cabin was built in 1931 as a taxidermy curio cabinet and became a roadhouse in 1939. It’s a classic honkytonk, filled with history: country legends Willie Nelson and Waylon Jennings have graced the stage, and a 14-year-old Tanya Tucker played her first gig here. It remains an all-American cowboy bar, where folks square dance to national and regional acts. Check the website.
3404 East Route 66, 928-526-9434, themuseumclub.com
14 Dollar Bill Bar, Oatman, Arizona
Oatman is a mining town with wild burros (donkeys) roaming the streets and shaking down tourists for treats. They are direct descendants of beasts brought to the area by gold miners in the 1800s. This restaurant was built in 1902, and Carole Lombard and Clark Gable honeymooned in the hotel upstairs. The walls are papered with more than 100,000 dollar bills, a legacy of the times when miners would stick a dollar on the wall with their name on it as their tab. Today the tradition continues, with tourists leaving signed bills wherever they can find a spot.
Oatman Restaurant, 181 Main Street, +1 928 768 4408, no website
15 Musso & Frank Grill, Hollywood, Los Angeles, California
Sip sublime martinis while you soak in the history at this bar that has been serving Hollywood A-listers since 1919. Charlie Chaplin, Greta Garbo, Humphrey Bogart and Lauren Bacall lounged in these red-leather booths and hobnobbed with literary legends, such as F Scott Fitzgerald and William Faulkner (he mixed his own mint juleps behind the mahogany bar). It’s still a place to see and be seen today. The cast and crew of Mad Men held their premier party here, and also used it to film the Red in the Face episode – the one where Don gets Roger drunk on martinis.
6667 Hollywood Boulevard, + 1 323 467 7788, mussoandfrank.com
Things to see en route
16 Chicago architecture
Explore America’s most iconic buildings with a Chicago Architecture Foundation tour by trolley bus, boat, bike, subway and Segway. More than 70 walking and bus tours take in Frank Lloyd Wright neighbourhoods and Mies van der Rohe’s Farnsworth House. Tourists and locals agree it is the best way to see Chicago. Check the website for schedules and book early.
architecture.org, tours $15-$85
17 Cadillac Ranch, Texas
This public art installation of graffiti-coated Cadillacs was created in 1974 by members of the art group Ant Farm. Tourists are welcome to bring spray paint and leave their mark, but it’s also great just to go and see 10 tail-finned Cadillacs buried nose-first in the west Texas landscape. A Route 66 icon.
Just west of Amarillo. Take I-40 to exit 60. Located along the frontage road (old Route 66), near Hope Road on the south side of 1-40. Free
18 Route 66 Gift Shop, Seligman Arizona
Once you arrive in Seligman, get an ice-cream cone at the Delgadillo’s Snow Cap Drive-In (301 West Chino Avenue) and then walk down the street to Angel & Vilma Delgadillo’s Route 66 Gift Shop & Visitor’s Center. Try to meet Mr Delgadillo, who is known as the “guardian angel” of Route 66. He is one of the warmest people you’ll ever meet and a great storyteller, with extensive knowledge about Route 66. Many of his stories inspired the film Cars.
22265 West Historic Route 66, +1 928 422 3352, route66giftshop.com
19 Casa del Desierto Harvey House, Barstow, California
The once-abandoned, now beautifully restored Casa del Desierto Harvey House was built in 1885 as a restaurant and hotel that served passengers on the Santa Fe Railway. It burned down in 1908 and was rebuilt by architect Mary Colter from 1910 to 1913. Once Amtrak dominated the railway system, many Harvey Houses were torn down. This building fuses 16th-century Spanish and classical revival architecture. While you’re there, check out the Western America Railroad Museum and the Route 66 Mother Road Museum.
681 North First Avenue, +1 760 256 8617, barstowharveyhouse.com. Free
20 Fair Oaks Pharmacy and Soda Fountain, South Pasadena, Los Angeles, California
A nostalgic corner drugstore where soda jerks have been pouring floats, phosphates, egg creams and lime rickeys since 1915. In addition to the old-school soda fountain and restaurant, there’s a fully functional pharmacy and drugstore. It’s the perfect place to pick up gifts such as Route 66 memorabilia, greeting cards, bath and beauty products, retro toys and rare vintage candies from Mary Janes to Bit-O-Honeys.
1526 Mission Street,+1 626 799 1414, fairoakspharmacy.net