Driving Route 66 in its entirety is an unfulfilled dream of mine. However, I have had my kicks on Route 66 along various sections in Illinois, Oklahoma, Texas and California, besides paying homage to where the fabled road begins and ends – marked by commemorative signs by the Art Institute of Chicago and on Santa Monica Pier.
Sampling it in small chunks, I have savoured its enduring appeal, historic landmarks and memorable attractions.
For example, the saloon-style Big Texan Steak Ranch in Amarillo, Texas serves up gigantic 72-ounce steaks and anyone downing the whole meal inside an hour eats for free. I resist the challenge but one fellow diner succeeds, earning himself a certificate and undoubtedly severe indigestion.
At Shamrock, Texas, I encounter the delightful, pink Conoco Tower Station, the only Art Deco petrol station on Route 66.
I stay in several roadside motels along the Mother Road in Texas and in Oklahoma, where I drive from Tulsa to Oklahoma City. And in California, I follow the final section from desert town Barstow, strolling the final few yards on Santa Monica’s venerable pier.
After those appetisers I’m now ready for the main course.
Route 66, otherwise known as the Mother Road, turns 100 on November 11, 2026 – but preparations to mark the centennial are already well under way.
And new road trip itineraries are being launched ahead of an expected surge in interest as the spotlight increasingly focuses on the historic route.
Nowhere is that more the case than in Oklahoma, which has the road’s longest driveable section of any state and where it has its roots.
The now legendary road came about thanks to Tulsa, Oklahoma, businessman Cyrus Avery, who successfully lobbied for a highway between Chicago and Los Angeles via Oklahoma as the Model T Ford was opening up driving to the masses.
Called the Main Street of America by Avery, Route 66 linked small towns and big cities in America’s heartland, spawning weird and wonderful roadside attractions to tempt travellers to stop, many of which still exist.
Illinois to California
Starting in Chicago and ending in Santa Monica, the route spans three time zones and eight states – Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California – and stretches almost 2,500 miles, more than 400 of them in Oklahoma.
The advent of fast interstate highways bypassing the long and winding road signalled its apparent death knell and Route 66 was decommissioned in 1985.
But its spirit was kept alive by enthusiasts, local administrations and businesses, a renaissance that saw Route 66 museums and more attractions popping up celebrating its glory days and motoring history.
The momentum is growing. Among planned events, the Illinois State Museum in Springfield is to stage a special exhibition commemorating the road’s 100th anniversary in 2026.
A nine-day festival of classic cars, historic memorabilia, music and food, the inaugural AAA Route 66 Fest was held in Oklahoma City and Tulsa in June 2022 with plans to stage it each year up to the centennial.
More festivities are also in the pipeline in the run-up to the big day. Meanwhile, efforts in Oklahoma include renewing Route 66 signage and neon lighting along the road as well as projects to renovate Route 66 motels.
Driving the entire route typically takes around two and a half weeks, but fresh fly-drive options are being introduced to allow visitors to take things at a leisurely pace.
Oklahoma Tourism is working with ATI on itineraries that break the route into two – a 16-day eastern journey that starts in Chicago and finishes in Grapevine, Texas, with flights from Dallas, and an 18-day western drive from Grapevine to Santa Monica.
The eastern drive allows seven nights in Oklahoma while the western option includes four nights, giving time to explore beyond Route 66 and delve into the state’s Native American culture, Western heritage and natural attractions.
A 21-day full Route 66 itinerary includes four nights in Oklahoma.
Matt Bates, UK, Northern Ireland and Ireland Destination Awareness Manager for the Oklahoma Tourism and Recreation Department, said that a number of tour operators were already including the hybrid east and west itineraries with their offerings and the full route option was available for them to tailor.
First Class Holidays Product Manager Brian Hawe said that while one-way car rental had been an issue for a while, the operator was now seeing availability for rentals from Chicago to Los Angeles, and there was demand for the route.
He added: “Historically it was the one-way fees that were a barrier to sales but we can now see those included in the rental cost, so while the customer is still paying for it, it’s something that’s been included in the overall cost when they book, and not something perceived to come out of the holiday money.
Speaking of the upcoming anniversary Hawe predicts an added interest when the centenary promotions start.
Where to book it
FIRST CLASS HOLIDAYS
A 17-night Historic Route 66 fly-drive from Chicago to Los Angeles including a two-night extension in Oklahoma costs from £2829pp including international flights, accommodation and 18 days’ car rental with unlimited mileage, zero excess and no one-way drop fee.