Route 66: How to tackle the world’s greatest road trip
Route 66 cuts through some of the most iconic scenery in the US - Cavan Images
Eight states, three time zones, 2,448 miles across a continent from Chicago to Santa Monica: Route 66 is the world’s best known road trip and on many a traveller’s wish list. It’s a journey that begins in a forest of skyscrapers and ends beside golden beaches, a chance to savour historic cities and widescreen landscapes, stroll through small town America, stay in classic motels, eat your best-ever burger and maybe buy yourself some fancy cowboy boots.
2026 is the centenary of the “Mother Road”. Celebrations kick off in Springfield, Missouri, on April 30 (the date the route was named) and peak on November 11 (the date the route opened), though many more events are planned along its length.
Route 66 was decommissioned in 1985, superseded by interstate highways, so there is no signposted road to follow – besides “historic route” signs at various points. Only purists track the full old route, the rest of us dip in and out as in some places the old and new (faster) roads run side by side. Most of the distances covered in this three-week itinerary are around a three-hour drive, which allows time to take a hike, shop and explore the small towns and cities along the route.
Days 1, 2 & 3
Chicago
Three airlines operate flights from London into Chicago and back from Los Angeles – British Airways, American Airlines and United. Moxy Downtown Chicago in River North is a central, mid-priced base with a fun, party vibe.
Make the most of the jet lag in Chicago and hit the Skydeck in Willis Tower before the crowds arrive - Mlenny
Jet lag means you will wake early so get to Skydeck in the Willis Tower for its 9am, crowd-free opening. Look west from the 103rd-floor observation deck – that’s the America you’ll be driving right across. To make sightseeing easy download the CityPASS app which offers discounted reservations for five attractions including this one, the 75-minute Shoreline Sightseeing Architecture River Tour and the masterpiece-filled Art Institute of Chicago. Be sure to take a selfie by the Route 66 start sign near its entrance.
When hunger calls, River Roast is justifiably famous for its chicken dishes, then catch some live blues at Buddy Guy’s Legends.
Day 4
Illinois
Pick up your car in Downtown Chicago and head north-west to Wilmington to admire the restored Gemini Giant, a 30ft ‘Muffler Man’ statue from 1965 – one of many put up along Route 66 to attract motorists to stop at restaurants.
Restaurants along Route 66 erect giant statues, like the Gemini Giant, to attract motorists - travelpix/Alamy
As the state vehicle license plates trumpet, Illinois is the ‘Land of Lincoln’; the 16th US president who resided in its capital, Springfield, from 1837-61. Check into the President Abraham Lincoln Springfield – a DoubleTree by Hilton Hotel, after a stop at the Illinois State Fairgrounds Route 66 Experience to see its vintage neon signs. For dinner, head to old school Italian restaurant Saputo’s.
Days 5 & 6
Missouri
Get up early to join the free, 25-minute guided tours of the Lincoln Home National Historic Site which offers insights into how the statesman enjoyed life here with his family and pets. Once back on the road, consider calling into Route 66 Motorheads Bar, Grill and Museum where dishes have witty names like hubcaps (fried pickles) and pistons (shrimp skewers). From here follow the old Route 66 via Auburn, passing through quiet countryside to reach the banks of the great Mississippi River.
Get stuck into some classic American cuisine at the Route 66 Motorheads Bar and Grill
A mighty metropolis founded by fur traders in 1764, St Louis has a huge green heart – Forest Park – where the 1904 World’s Fair was held. Stay beside its north-east corner at the monumental Royal Sonesta Chase Park Plaza, which opened in 1922. Visit the free-entry Missouri History Museum, followed by dinner at buzzy Yellowbelly (order the Moroccan-spiced grouper).
Book tickets to ride up the 630ft Gateway Arch, designed by Eero Saarinen and opened in 1966. The companion museum, which details how the nation expanded west from here, is one of the best on Route 66. On the city’s western edge, the National Museum of Transportation has fabulous classic cars to drool over, as does the Route 66 Car Museum in Springfield (Missouri), 230 miles west. This is where the idea of Route 66 was born on April 30, 1926. Visit its History Museum on the Square and bed down at the Best Western Route 66 Rail Haven, a budget motel that comes with a small pool and a sign proudly stating “Elvis stayed here”.
Days 7 & 8
Oklahoma
Continuing west, the south-east corner of Kansas has a mere 13 miles of Route 66 centred on a restored 1939 gas station in Baxter Springs. After that you’re in the flat, deserted fields of Oklahoma with Tulsa, which considers itself the ‘official capital of Route 66’, just a couple of hours away. Book an expert-led walking tour to experience how the city changed after the discovery of oil in the region, with its art deco skyscrapers and secret passages.
Base yourself at the characterful Mayo Hotel, which opened in 1925, and dine at The Vault, which serves American comfort food in a 1959 bank. Before heading off the next morning, drop into the excellent Bob Dylan and Woody Guthrie Centers, which are next to each other.
Pick up an authentic cowboy hat and get it shaped by Gary Sorrell in Langston’s - The Washington Post
Back at the wheel, Oklahoma has more than 400 miles of the original Route 66 to savour, parts of which are marked as State Highway 66, with your next stop “mighty pretty” Oklahoma City. Park the car at the Classen Inn, a 1963 motel that’s had a cool and colourful makeover, then take a cab to Stockyards City to buy those cowboy boots – Langston’s Western Wear stocks over 10,000 pairs. Dine at McClintock Saloon and Chophouse which serves hand-cut steaks and has more than 200 whiskeys.
Day 9
Texas
Saddle up your vehicle and head to the National Cowboy & Western Heritage Museum where there’s plenty to contemplate from a 1868 stagecoach to Hollywood’s love affair with the Wild West – where you are now heading. As you cross into Texas on I-40, which replaced Route 66, it’s time to savour the open road and big skies as the soil reddens and every turn-off seems to lead to a ranch.
Hit Texas and you’ll start to see Hollywood’s love affair with Route 66 on every corner - Melissa Kopka/iStock Editorial
Pull over in Shamrock, where the Conoco Tower Station – an art deco gas station from 1936 – and the U Drop Inn dishes up Mom’s Meatloaf with a side of Route 66 nostalgia. Overnight in Amarillo at the Big Texan RV Ranch; in the evening picnic on your deck or head over to the companion Steak Ranch & Brewery for a raucous meat-fest.
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Days 10, 11, 12 & 13
New Mexico
Now you are almost half-way through your epic journey, a milestone flagged in the tiny settlement of Adrian where the Midpoint Cafe is famous for its pies – fancy a slice of apple and green chilli? Before you call in, take a half-hour detour south to the vast Palo Duro Canyon State Park where a one-way loop lets visitors drive through an elemental landscape of rocks that was inhabited 15,000 years ago.
Midpoint Cafe marks the halfway point on your road trip - Eva Worobiec / Alamy Stock Photo
As you cross into New Mexico put your clocks back an hour as you are now on Mountain Time. Your next pit-stop, Tucumcari is an archetypal Route 66 community with a string of motels new and decayed. Check into the spruced-up 1959 Motel Safari then take a stroll along the neon-splashed highway to see the Blue Swallow and Roadrunner Lodge.
The next day, if you’re feeling the heat, take a dip at the Blue Hole in Santa Rosa, then swing north to Santa Fe for a rare luxury – two nights in the same place.
At 7,199ft this is the highest state capital in the US and was part of Route 66 until 1937. With its low-rise adobe buildings and wealthy, arts-loving residents, it feels like another country. Base yourself at the lively La Fonda on the Plaza which occupies an entire block and has free art tours.
Motels, new and decayed, still line the infamous road - pyzata/iStockphoto
Top sights here are the Georgia O’Keefe Museum and Museum of Indian Arts and Culture with the garden of the accomplished Restaurant Martin a good choice for dinner with treats that include a prickly pear margarita.
If you want to get close to the countryside, book a ride with Tamaya Horse Rehabilitation, north of Albuquerque, or push on west to Gallup to learn about Native American culture. The Richardson Trading Company, established in 1913, stocks quality local crafts while the free-entry Gallup Cultural Center explains how the Navajo nation played a vital role in the Second World War. Spend the night at El Rancho Hotel, which opened in 1936 and hosted many Hollywood movie stars.
Days 14, 15 & 16
Arizona
Arizona is home to the longest unbroken stretch of the old Route 66, 158 miles from Ash Fork to Topock. The state is home to a panoramic desert landscape that typifies the Wild West with its mesas, buttes and monumental cacti. Drink it in at the Petrified Forest, the only US national park on Route 66, where huge fossilised logs, 2,000 year-old petroglyphs and the 1937 Painted Desert Inn wind back the clock.
The Petrified Forest is the only US national park on Route 66 - AscentXmedia/Getty Images
In Holbrook, the free-entry Navajo County Historical Society Museum fills an 1898 Court House and includes a grim jail in use until 1975. Accommodation is basic at the photogenic Wigwam Motel with its 1950s concrete teepees and 30 vintage cars – for something more upscale, drive on to Winslow’s La Posada, a 1930s gem enlivened with engaging celebrity portraits by co-owner Tina Mion. En route, don’t miss the Meteor Crater, an astonishing hole in the ground that was created 50,000 years ago and is almost a mile wide.
Spend the night in Flagstaff at the space travel-themed Americana Motor Hotel – this was the world’s first international Dark Sky City, designated in 2001, and the Lowell Observatory offers stargazing evenings. Drive north to the Arizona Snowbowl and take a serene, 10-minute gondola ride up Mount Humphreys for a view that stretches as far as the Grand Canyon.
Arizona’s main streets have classic Route 66 flare - jordi clave garsot / Alamy Stock Photo
Drive to Kingman via Seligman, whose residents started the campaign to preserve the Mother Road in the 1980s. For your final stop in this exhilarating state pull up at Tin Can Alley for a cosy night’s sleep in a vintage Airstream trailer and probably the best coffee and ice cream of the whole trip.
Day 17, 18, 19 & 20
California
After checking out the Powerhouse Route 66 Museum, which includes a display of early electric vehicles, call into the Kingman Turquoise Mine, on the outskirts of the city, to buy loose turquoise stones and locally-made jewellery. Next take the highly scenic road to Oatman which includes, for the first time on this long adventure, hairpin bends. Cross the Colorado River to reach the Golden State and a long and somewhat monotonous high desert drive towards the Pacific Ocean. Break the journey in Barstow where you can catch an open-air movie at the Skyline Drive-in Theater (stay at the modern Fairfield by Marriott Inn & Suites Barstow).
Swim in the Pacific Ocean on Santa Monica Beach to mark the finish line - Aaron P/Bauer-Griffin
Now it’s time to do the freeway fandango as the backroads bliss of Route 66 morphs into the fast-paced, six-lane highways of Greater Los Angeles. Your journey officially ends in Santa Monica at the junction of Lincoln and Olympic Boulevards where the enjoyably retro Mel’s Drive-In restaurant does a fine R-66 burger.
How do you celebrate driving across the breadth of America? By checking into the upbeat The Pierside Santa Monica which is steps away from the beach and Santa Monica Pier with its 1922 carousel and fairground rides (best at night). Go for a cocktail at the grand beachfront Hotel Casa del Mar then feast on oysters, brandade and artisanal cheeses at Esters Wine Shop.
Santa Monica is the end point of your Route 66 adventure - Tony Andrews Photography
Day 21
Homeward bound
Have you got your kicks? The last leg of your epic drive is a 25 minute hop from Santa Monica to Los Angeles Airport to drop off the car and fly home with a trunk full of memories.
How to do it
When to go
Spring and autumn are best weather-wise. Summers are hot so choose hotels with a pool and carry plenty of water.
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'What to book
Blow the budget: Original Travel (0203 958 6120) offers tailor-made journeys with a 23 day ‘Epic Route 66 Road Trip’ from £4,305 per person including flights, car and accommodation.
Cost-effective: Travelbag (020 3944 2468) has a 22 day ‘Explore Route 66’ itinerary travelling by motorhome from Chicago to San Francisco from £1,349 per person including flights.
More information
Lonely Planet’s Best Road Trips Route 66 is a dedicated guide and includes directions. Useful additional information can be found at americathebeautiful.com/road-trips and visitheusa.co.uk.
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