If there’s one road that has defined America’s spirit of freedom, rebellion, and discovery, it’s Route 66. This route, aptly coined the “Main Street of America,” begins in Chicago and ends in Santa Monica, Cali.

And in 2026, the Mother Road turns 100 years old. 

But Illinois, where the Route 66 journey begins, isn’t waiting until next year to start celebrating. In June 2025, the Illinois Office of Tourism is hosting a media event to ignite the countdown. 

And what better way to commemorate this than by doing exactly what Route 66 was made for - riding it.

Ten riders are all ready to throw a leg over machines rented from Twisted Road in Chicago and head straight into the nostalgic soul of America. 

And the best part? Most are from tourism boards or news outlets from across the globe, from as far away as the Netherlands and Brazil. 

Their mission: experience the first 300-ish miles of Route 66 from Chicago to St. Louis. 

Their weaponry? A lineup of two-wheeled icons built for the open road (and some whys behind the choices):

• Honda Shadow: The cruiser that won't quit. Comfortable and stylish without being flashy, the Shadow held its own in every small town stop.

• Kawasaki Mean Streak: Aggressive, torque-rich, and surprisingly comfy, the Mean Streak carved up Illinois’ long straightaways with ease.

• Harley-Davidson Sportster: No bike brings more attitude per cubic inch than a Sportster. Perfect for short blasts and bar-stool stops.

• Harley-Davidson Fat Bob: Big, bold, and angry-looking, the Fat Bob attracted stares at every gas station. It’s a bar-fight on wheels—in a good way.

• BMW R1200 GS: You’d think a GS would be out of place on a flat road ride. Think again. Its comfort and versatility make it a sleeper hit.

• Honda Goldwing: The king of comfort. If Route 66 had an official touring throne, the Goldwing would sit atop it.

• Harley-Davidson Road King Classic: Chrome, leather, and that unmistakable thump, this machine owns the road like a Sinatra song.

• Harley-Davidson Street Glide (x2): Two riders. Two Glides. No arguments. Street Glides dominate Twisted Road’s rental list for a reason—they’re perfect for rides like this. Batwing fairing. Floorboards. Saddlebag capacity for days.

• Yamaha FJR1300A: Precision meets endurance. The FJR is the scalpel of sport touring, devouring Illinois tarmac with quiet ferocity.

There’s no surprise seeing two Street Glides on this list. Smooth, powerful, and dressed for highway swagger, it’s the quintessential modern Route 66 ride. This bagger is one of the most-rented platforms on Twisted Road, along with the BMW GS and Honda Gold Wing.

Why Start in Illinois?

Simple. Because Illinois is the birthplace of Route 66.

Route 66 was officially commissioned on November 11, 1926, starting at East Adams Street in downtown Chicago. 

The original sign hung just steps from Lake Michigan, connecting the Windy City to the golden dreams of Santa Monica, California. Illinois is where dreams turned into miles.

What makes the Illinois stretch so unique is its tightly packed blend of Americana kitsch, historical touchpoints, and mom-and-pop spirit. It's flat, fast, and rich in reminders of the postwar boom, when road trips meant paper maps, greasy diners, and wide eyes staring out the back window.

The Ride: Chicago to St. Louis

Here’s what you can expect if you decide to take this trip.

Chicago:

Before twisting throttles, gather at the Route 66 “Begin” sign at the intersection of East Adams Street and Michigan Avenue. The city is loaded with the type of energy only known in Chicago, just as New Orleans, NYC, or LA. 

But for riders, there’s something surreal about staring west down the highway that’s inspired music, novels, and a million miles of stories.

Grab a coffee at Lou Mitchell’s, which has been open since 1923, and soak in that smell of hot griddle, fresh doughnuts, and anticipation. This is a tradition. And traditions matter on Route 66.

Joliet:

Riding south, you’ll hit Joliet, home to the famed Rialto Square Theatre and the Old Joliet Prison (yes, that one from The Blues Brothers). Keep your eyes peeled for the Gemini Giant in Wilmington, one of many fiberglass Muffler Men that guard Route 66 like silent giants.

Dwight:

Next stop is Dwight, home to an impeccably preserved 1930s Texaco gas station. Riders on Goldwings and FJR1300As will eat this up: crisp lines, retro pumps, and just the right amount of rust make for the perfect ride-break photo op.

Pontiac:

Pontiac delivers Route 66’s soul in full technicolor. The Route 66 Hall of Fame and Museum lives here, and it's mandatory for every two-wheel traveler. There’s also an entire alley painted with murals depicting Route 66’s history.

The BMW R1200 GS and the Kawasaki Mean Streak, more known for performance than plush, will discover smooth rural roads here to stretch their legs.

Atlanta and Lincoln:

Not to be confused with the state capital, the town of Lincoln gives riders a chance to park under the world’s largest covered wagon. 

And in Atlanta, Illinois (population: small), the riders discover Palms Grill Cafe, a restored diner that feels frozen in time.

The Fat Bob and the Sportster riders will love it here. Minimal electronics. All soul.

Springfield:

This is Abe Lincoln’s town, but it’s also home to Cozy Dog Drive-In, the birthplace of the corn dog on a stick. Forget counting calories. Count flavors instead.

Riders on the Road King Classic and Shadow will feel the vibe shift here. More locals wave. More trucks honk. Route 66 isn’t just nostalgia—it’s a living road.

Litchfield to Staunton:

Past Springfield, Litchfield welcomes with the Ariston Cafe, one of the oldest Route 66 restaurants. Grab a slab of pie, then rumble south to Staunton’s Route 66 Chain of Rocks Bridge.

Here, the Mississippi whispers: "Welcome to the gateway to the West."

St. Louis:

The ride technically ends across the river, but the heartbeat of this trip begins here. Riders pull into town under the shadow of the Gateway Arch.

There's a feeling in your bones—an odd mix of road fatigue and emotional surge. You've just retraced the path millions have taken before you. And you've done it the way it should be done: on two wheels, with wind in your face, and history around every corner.

The Road Ahead

The Route 66 Centennial will pull travelers from all over the globe in 2026. But the soul of the journey, the part that sticks with you, starts in Illinois.

And Twisted Road is making that beginning more accessible than ever, just as the 10 international tourism specialists and journalists will experience in June. 

If you’ve never done Route 66, now’s the time. Whether you’re riding a Sportster or a Street Glide, it’s not about the bike, it’s about the ride. The neon. The grease. The ghosts of yesterday’s travelers cheering you on from every mile marker.

Start in Chicago. End in St. Louis. Remember it forever.