Agents on the Open Road: RoadTrips USA Edition – Historic Route 66

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Welcome to part two of Brand USA’s Agents on the Open Road: RoadTrips USA Edition, in partnership with Travel Gossip and Gold Medal.

This month’s feature focuses on the iconic Route 66, which stretches from Chicago, Illinois to Santa Monica, California. Read the feature, then answer the question at the bottom of the page and you could win a £50 One4All voucher and enter a grand prize draw to win a £5,000 Gold Medal voucher that can be redeemed against any 2025 Gold Medal USA package holiday.

Travelling from east to west, the Historic Route 66 itinerary covers Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California, sticking as closely as possible to the old two-lane Route 66 and including quirky roadside attractions and classic Americana diners along the way. Full details of the Route 66 trip can be found here, and below is a day-by-day snapshot of what can be discovered along the way.

Day 1, Chicago to Springfield, Illinois

Start with breakfast at Lou Mitchell’s, a Chicago institution, then take your first selfie on Adams Street, next to the Route 66 insignia and a sign reading: BEGIN. Then head off, staying on the two-lane original Route 66 where possible. At Joliet, Illinois, explore the Route 66 Museum and find out about the Muffler Men fiberglass statues used along the Route in the 1960s to advertise auto repair shops, diners and other roadside attractions.

Day 2, Springfield, Illinois to St Louis, Missouri
The Chain of Rocks bridge, over the Mississippi River

Visit Oak Ridge Cemetery, the final resting place of President Lincoln, then head to the Litchfield Museum & Route 66 Welcome Center before lunch at the Ariston Café, one of Route 66’s oldest restaurants. Cross the Mississippi River on the Chain of Rocks bridge.

Day 3, St. Louis to Springfield, Missouri

Visit the Jesse James Wax Museum at Stanton in the Missouri Ozarks and his reputed hideout at Meramec Caverns. In Cuba you’ll find the Wagon Wheel, the oldest continually operated motel on Route 66, with its original neon sign, then visit Springfield’s Route 66 Car Museum.

Day 4, Springfield, Missouri to Tulsa, Oklahoma

Stop off at Carthage to see the 66 Drive-In Theatre before heading to Galena, Kansas. Visit Rainbow Bridge, which crosses Brush Creek. Ribbon Road is the narrowest and oldest segment of Route 66.

Day 5, Tulsa to Oklahoma City, Oklahoma

Attractions include Buck Atom’s Cosmic Curios, a former gas station; a famous Muffler Man and the Golden Driller, a 22-meter-tall monument to Tulsa’s rich oil history. Stop off at the Cyrus Avery Centennial Plaza, which pays homage to the Tulsa resident known as the Father of Route 66.

Day 6, Oklahoma City, Oklahoma 

Here you’ll find another iconic landmark, The Milk Bottle Grocery and the Oklahoma State Capitol with a dome that features a five-feet-tall bronze statue of a Native American figure, depicting characteristics of each of the state’s 38 federally recognised tribal nations.

Day 7, Oklahoma City to Amarillo, Texas

Visit Clinton‘s Route 66 Museum to experience the story of the Mother Road as you listen to the big band music of the era, sit in a booth at a 1950s diner and learn about life on the road through images and sounds.

Day 8, Amarillo, Texas to Tucumcari, New Mexico
Cadillac Ranch, halfway point of Route 66

After the famous Cadillac Ranch, a striking installation made up of 10 graffiti-covered Cadillacs buried halfway in the dirt in the Texas desert, is the halfway point of Route 66, marked by the Midpoint Café in Adrian.

Day 9, Tucumcari to Albuquerque, New Mexico

Stop off at the Tee Pee Curios gift shop and have breakfast at retro diner Kix on 66 before leaving Tucumcari. Take a dip in the Blue Hole in Santa Rosa, then take the original Route 66 northwest to reach downtown Santa Fe. Have dinner at the 66 Diner, housed in an old Phillips gas station in Albuquerque.

Day 10, Albuquerque, New Mexico

Tour the Old Town and Downtown areas of Albuquerque along the stretch of Old Route 66 now known as Central Avenue.  Stop for lunch at the Dog House Drive In, featured in Breaking Bad and Better Call Saul.

Day 11, Albuquerque, New Mexico to Holbrook, Arizona

In Arizona, visit one of Route 66’s natural wonders, the Petrified Forest National Park. Stay in an oversized teepee at the iconic Wigwam Village Motel #6.

Day 12, Holbrook to Flagstaff, Arizona

Stop off in Winslow at La Posada Hotel for breakfast in the famous Turquoise Room. Opened in 1930 as one of the most luxurious hotels in the Southwest, this Arizona gem was restored to its former glory in the 1990s and is still one of the most popular stops along Route 66.

Pay homage to The Eagles’ first hit, Take it Easy, which references Winslow by name. Then stop at Meteor Crater, where a meteorite fell to Earth some 50,000 years ago. From Flagstaff, take a 90-minute drive to Grand Canyon National Park, Arizona.

Days 13 and 14, Flagstaff, Arizona to Las Vegas, Nevada

Take a detour from Route 66 and head to Las Vegas, passing colourful vintage gas stations, cafés and stores, all restored to their original glory in Seligman and visit the Arizona Route 66 Museum in Kingman. Stay overnight on Days 13 and 14 in Las Vegas.

Santa Monica Pier

Day 15, Las Vegas, Nevada to Santa Monica, California

Pass through the Joshua Tree National Park, California, before rejoining Route 66. Visit the Route 66 ‘Mother Road’ Museum in Barstow, then head towards the Pacific Coast, where Cajon Boulevard offers stunning mountain views of Cajon Pass as it joins up with Old Route 66. In Downtown Los Angeles, join Sunset Boulevard then follow Santa Monica Boulevard through West Hollywood to Beverly Hills, arriving at Santa Monica Pier, where a sign marks the official end of the Mother Road.

Agents’ views

Liverpool-based independent travel agent Julie Hendrickson, who runs Easy Travel with Julie, took five weeks over two visits to complete Route 66, taking side trips along the way.

“We spent four nights in Chicago before picking the car up and heading out. We started with breakfast in Lou Mitchell’s Restaurant as it’s the iconic place to eat to start the route. We visited Springfield, and St Louis, took a side trip to Branson for five nights, then Joplin (all in Missouri), then Tulsa and Oklahoma City, both in Oklahoma, before driving back to Chicago.

For the second part, we flew into Oklahoma and drove the Amarillo to Albuquerque route, then took a train up to Santa Fe, on to Gallup, Hollbrook and Flagstaff.

We took a side trip to Sedona for five nights, and from there we took a steam train through a valley. We drove up to Monument Valley for an overnight and visited Lake Powell and Antelope Canyon before continuing to Needles, Barstow and Santa Monica, where we stayed for three nights and then took another side trip to Palm Springs.

The route and scenery are so different as you drive across the different states, from forests to deserts. The trip would suit clients who don’t need to take children, but it’s for any age group. I would suggest going when its warm: May to October. I would help plan the route with a client and talk about how many nights each stop needs from my experience.”

Not Just Travel agent Emma Summerill drove along Route 66 as part of a larger road trip in Arizona.

“Petrified Forest National Park is the first stop on the Route 66 map when you enter Arizona from neighbouring state New Mexico, travelling west.  It’s a fascinating park that is often overlooked. The 225 million-year-old trees turned into rock are really impressive but the landscape is the real stand out. From the Blue Mesa bands to the wide expanse of the Painted Desert, we felt like we entered another planet!

We stayed the overnight in the small city of Holbrook. Here we passed by the Wigwam Village, an iconic site on the road since 1937.  There is a bunch of vintage cars outside so you can take some fun pictures. 

For fans of the Eagles song Take it Easy, stopping at Winslow is a must. They have dedicated a whole area to “Standing on the corner in Winslow, Arizona” and subsequent lines in the song.  It’s a rite of passage to have your picture taken with the statue of Glenn Frey.  But the rest of the town is worth an explore too, with shops selling Route 66 merchandise and the famous song playing in pretty much all of them! The Sipp Shoppe is also a must for that true American diner experience. Their Italian sodas are delightful. 

Flagstaff is the largest stop on the route in Arizona.  There is a lot to do here including the Lowell Observatory, which has been at the forefront of American space exploration for 130 years. We visited Walnut Canyon National Monument, an important cultural site containing over 300 Native American cliff dwellings hollowed out of the canyon walls. It also has stunning views and opportunities to see loads of wildlife. 

Our final stop was in Williams, often touted as the gateway to the Grand Canyon, where you can see the Grand Canyon Railway and Bearizona Wildlife Park.”

There are plenty more road trip suggestions on the USA Itineraries section of the Brand USA website.
Also check out the newly refreshed Brand USA training platform.

Gold Medal offers 15 nights staying in various hotels along the route, with Alamo car hire (Toyota Corolla or similar, pick up ORD, drop off LAX, including Alamo’s Skip the Counter service), with flights departing London Heathrow on 11 September 2024, from £2,059 per person, based on two sharing. Quote ref 41813322

To book this or any USA RoadTrip itinerary, call 0800 014 7777 or visit

Answer this month’s question to enter the draw

The closing date to enter this month’s draw is 4 July 2024. View the competition Terms & Conditions.

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