I’m 103 floors up on the Willis Tower Skydeck in Chicago, peering down at the city in miniature. My eyes dart around as I scan the powder-blue skyline and streets below for familiar landmarks, such as Anish Kapoor’s striking Cloud Gate sculpture in Millennium Park, with its stainless-steel, bean-shaped curves. It’s too far away, but there are plenty of skyscrapers.
The buildings are a glance from the start of the best-known landmark, Route 66, which unfurls like a silver ribbon west, past skyscrapers, sleepy suburbs and into distant pancake-flat fields of corn that carpet so much of Illinois.
Stretching 2,400-plus miles (3,800 kilometres) from Chicago to Santa Monica, California, Route 66 opened in 1926.
It’s a regular fixture in popular culture, from John Steinbeck’s 1939 novel The Grapes of Wrath to the 2006 animated Pixar film Cars, and remains the classic US road trip.
Although it isn’t a single highway, rather a collection of segments preserved as Historic Route 66 after it was decommissioned in 1985 when the fast Interstate Highway System was introduced.
The 100th anniversary of Route 66 has triggered a spike in interest. UK tour operator Original Travel reports a 300 per cent increase in bookings for Route 66 holidays between 2025 and 2026. A packed schedule of festivals, exhibitions and community gatherings to celebrate the centenary is already under way.
Meanwhile, as electric vehicle (EV) sales surged in the US (the country’s Bureau of Transportation reports a 423 per cent rise since 2021), states and businesses have been working to improve charging point infrastructure along its length.
There are now regular charging points, making it possible to drive the whole thing in an EV. I’m testing part of it on a five-day trip across the 280-mile stretch in Illinois.
I’m in the city for the start of my own road trip by EV. Back on the ground, near the start of Route 66, I slide into my electric hire car, which can travel 300 miles on a full charge. With petrol topping $4 per US gallon for the first time since August 2022, this spring is an opportune time to try the route by EV.
A supercharger promises a full battery in around 20 minutes – charging times vary depending on what points you use – and costs around $8 to $18 per charge.
I’ve split my journey into bite-sized distances that promise a hit of Americana, flanked with detours into backcountry. To avoid range anxiety, a term coined to describe EV drivers’ concerns that they might run out of power before reaching their destination, I have carefully planned my route between charging points.
30 miles in, I pull over to enjoy fried chicken and corn fritters at the antique-filled White Fence Farm restaurant in the village of Romeoville. Here, I also find an epic collection of vintage cars, such as a turquoise 1964 Lincoln Continental and light brown metallic 1937 Le Salle convertible. Eight miles on, I wander the echoey corridors of the Gothic Old Joliet Prison, which featured in the 1980 film The Blues Brothers.
It stopped operating as a prison in 2002 and is now a tourist attraction that tempts road trippers (I notice EV charging points in the car park).
The sun is starting to set when I come face to face with my first muffler man: the Gemini Giant near the town of Gardner.
Originally located outside the Launching Pad Drive-In Restaurant (which closed permanently in 2022) in next-door Wilmington, this 30ft-tall hulk of green (inset) is one of around 200 fibreglass sculptures set on US highways.
They first appeared in the 1960s as a way for restaurant owners to attract hungry drivers.
When I arrive in Dwight, 80 miles southwest of Chicago, I locate a supercharger and plug in. Then I press on to Starved Rock State Park, known for its sandstone canyons. It’s a worthwhile detour 40 miles west – and I spend the night in a two-storey treehouse with a charging point.
“Most folk travelling Route 66 don’t venture over here, but they’re missing out,” says Thomas Aussem, the owner of Awesome Ottawa Tours in the historic town of Ottawa a few miles away. We walk along the Illinois Canyon Trail through forest carpeted in bluebells to Eagle Nest lookout. “Bald eagles were recently spotted nesting here,” he says.
I wish I could stay in the area another night, but the mural-clad city of Pontiac, back on Route 66, 40 miles south, beckons. Here, I plug in at another supercharger and head for the Route 66 Association Hall of Fame and Museum complex.
A sticker-covered 1970s VW Campervan full of drawings and Route 66 memorabilia is the star. It belonged to the late Bob Waldmire, a local artist, and it inspired the character of Fillmore, a 1960 Volkswagen Type 2 peace-loving bus in Cars.
I leave Pontiac the next morning and drive 190 miles to the Illinois state capital, Springfield, including on a red-brick paved part of the original Route 66.
“Roadies live for these historic sections dating to the early 1900s when bricks were used to make roads,” says Angela Wolfgram of Visit Springfield.
She chats to me at the Cozy Dog Drive-In Diner. It opened in 1949 and is laden with Route 66-related memorabilia.
More hits of Americana ensue on my drive, including thrift shopping at the Pink Elephant Antique Mall in Livingston, distinctive for its collection of giant fibreglass models (including one of Marilyn Monroe), eating cheesecake at the 102-year-old Ariston Café in Litchfield and getting a photo of the world’s largest catsup (ketchup) bottle in Collinsville.
When I reach Edwardsville, 85 miles south of Springfield. I head for the Unesco-listed Cahokia Mounds State Heritage Site nearby.
A transportive walk with site superintendent Lori Belknap takes in grassy trails running through an ancient landscape once home to a thriving community of 20,000 Native Americans.
All too soon, it’s dusk and I’m at my last stop: the Prairie Fruits Farm and Creamery.
Owner Lauren Brokish shows me around her family-run operation. She slides open a barn door, and I let out a gasp.
Inside, 30-odd playful baby goats are jumping around, waiting to be fed. It’s an experience I think about over dinner at the farm’s candlelit small-plate restaurant, Caprae, and realise that my electric journey on Route 66 is coming to an end just as it began – on a high.
Booking it
The writer was a guest of America As You Like it and Enjoy Illinois. America As You Like It has an eight-night Discover Illinois fly-drive from £1,125pp, including return flights from Heathrow to Chicago on United, fully inclusive car hire, two nights in Chicago, two nights in Springfield, one night in Alton, two nights in Galena and one night in Rockford. americaasyoulikeit.com; enjoyillinois.com
