Dubbed the “Mother Road” by John Steinbeck in The Grapes of Wrath and known as “Main Street USA,” U.S. Route 66 will celebrate its 100th anniversary in 2026. No other road in America had such an impact on growth, migration, transportation, and popular culture. During the Great Depression and the horrific Dust Bowl of the 1930s, Route 66 was a paved pathway to a better life, transporting tens of thousands of people from the heartland to the West.

Right after WWII, my Uncle Don traveled from California to his hometown of Springfield, Illinois, using much of Route 66 and riding a kickstart, air-cooled, single-cylinder AJS. As I pondered my own journey on the Mother Road, it seemed fitting to attempt it on my 1978 Yamaha SR500, which is also an air-cooled, kickstart Single. Over the years, I have owned several Yamahas, but the SR500 has been my preferred ride for its light weight, effortless cornering ability, competent disc brakes, and simple but elegant design. I like it so much, I own two.

For my trip, I chose the one with 30,000 miles on the odometer. Except for upgraded brake hoses, it was bone stock. To get it ready for my Route 66 adventure, I gave it a complete engine and chassis overhaul, as well as a 535cc big bore kit, an oil cooler, and a SuperTrapp exhaust. I retained the stock air box and K&N air filter but re-jetted it as required. The new chain and sprockets were one tooth larger on the countershaft, which lowered cruising rpms and resulted in a mostly vibration-free ride.

Related: 2015 Yamaha SR400 Review | First Ride

The SR500 also has a no-frills CDI ignition system with a strong charging system, allowing me to keep my cellphone and Bluetooth full of juice, and a centerstand, a must-have for daily chain lubrication and fixing flat tires (I had one).

Find out more about the First 100 Miles of Route 66

Since Route 66 starts in Chicago, I transported my bike from my hometown of Merritt Island, Florida, in my Chevy van. The first day of riding started in Chicago rush-hour traffic on the Kennedy Expressway, which was undergoing road construction, but after stop-and-go for two hours in record heat, I was rewarded with the U.S. 66 “Begin” sign at the corner of Adams Street and Michigan Avenue across from The Art Institute of Chicago. Just a few blocks away is the Willis Tower (formerly the Sears Tower), and a few blocks farther is the famous Lou Mitchell’s restaurant, which is over 100 years old and served a great breakfast to start my trip.

Aside from the sweltering temperatures and humidity of August, Chicago’s beautiful residential areas and parks made the short trip to the suburbs quite pleasant. The first 100 miles of Route 66 is known as the Heritage Corridor, which also includes towns along the Illinois & Michigan Canal, which connected Lake Michigan to the Illinois River, and Starved Rock State Park. In Cicero, I stopped to see one of Al Capone’s houses. In Berwyn, I checked out the world’s largest laundromat, which is over 13,000 square feet and even has a bird aviary, and I also passed by one of the oldest-operating White Castle restaurants.

Traveling south, I found a neat roadside display in the town of Joliet called Dick’s on 66, an old towing shop decorated with several vintage vehicles and a patch of bricks purportedly from the original Route 66. Across the street is a restored gas pump and ice-cream shop. Joliet is also the home of the state prison and was featured in the 1980 movie The Blues Brothers.

In Wilmington, Illinois, I cooled down with a sundae at the Route 66 Creamery and spotted the first of five “giants” I would see on my trip: a Sinclair dinosaur on the roof of G&D Tire Company.

For this trip, I tried to take the oldest sections possible of Route 66, and Illinois had them clearly marked. Some sections of road looked more like abandoned driveways, with weeds growing through cracks in the concrete. My little SR500 was perfect for this kind of duty.

In Towanda is Dead Man’s Curve, a sharp curve that caught many drivers unaware and was the site of numerous accidents from the 1920s to the 1950s. There’s even a preserved series of Burma Shave signs that say: Around the curve / lickety-split / beautiful car / wasn’t it? I had a 25-plus mph headwind for most of that first day, and it felt as if I was riding into a blow drier. My first night was spent at the Ghost Hollow Lodge in Chandlerville, Illinois, where I fortified myself with a dinner of venison and fresh veggies.

On the second day, I stopped in Springfield to cool down with an iced tea at Route 66 Motorheads Bar & Grill, which also has a museum and gaming room. Just south of Springfield in Carlinville, my fun was interrupted by a flat tire. I had packed tools, tire irons, a portable compressor, and a tube patch kit, but my tube was too badly mangled by the nail. Scott McDaniels of S&S ATV came to the rescue by delivering a new tube (at no charge), a local resident across the street brought me ice water, and the local city hall allowed me to do the work on the north side of their office in the shade on the concrete. It just goes to show how kind strangers can be when you are in a bind.

The repair set me back almost four hours, and I had to bypass many of the Route 66 sights from Carlinville to St. Charles, Missouri, where I stayed with friends. The following day, I unloaded my luggage and backtracked to Granite City, Illinois, to see the Old Chain of Rocks Bridge. The mile-long bridge was part of the original Route 66 from 1936 to 1965 and allowed motor vehicles to cross the Mississippi River from Illinois to Missouri. It features a 30-degree turn partway through. I had gone over this bridge in a car as a kid before it was decommissioned in 1968. It is now only open to foot traffic and bicycles.

While in St. Louis, I also went up into the 630-foot Gateway Arch, which was completed in 1965. It is now part of the National Park Service, and with recent remodeling and upgrades, it’s a not-to-miss experience. I also visited the National Museum of Transportation on the west side of St. Louis. This may be one of the best transportation museums in the country and has the only remaining GM Aerotrains. It also has a running Chrysler Turbine Car like the one at the Henry Ford Museum in Michigan.

After getting my luggage loaded back on the SR500, my next stop was Times Beach, Missouri. Route 66 used to cross the Meramec River there, and the remnants of the bridge are still there, along with a Route 66 State Park. I met some folks from Europe riding Route 66 on rented Harleys, and they were aghast that I was attempting to make the same trip on my antique bike with no GPS navigation and only an EZ66 guide in my tankbag.

Times Beach was the site of the second largest EPA Superfund site due to a local contractor spraying dioxin on the dirt roads for dust control. All the buildings were bought by the EPA and leveled, and it’s currently considered a ghost town. West of Times Beach is the Meramec Caverns, where I ran into my new European friends again. My bike would do roughly 100 miles per tank of fuel, which coincided with my body’s need to stand up and stretch out a bit and suck down a cold beverage.

I stayed at the KOA in Springfield, Missouri, that night and rented a cabin. I had planned on renting a primitive campsite, but for only about $40 more, I got an air-conditioned cabin, lights, electricity, a mattress, a table, and a TV. It was a bargain!

Along the way in Missouri are a few museums and stops such as a replica 1930s Sinclair station called Gary’s Gay Parita in Ash Grove, Missouri, where the sign reads “Gas Wars” and advertises fuel at 15 cents per gallon. Another sign reads “Kendal, your 2,000 mile oil!” We have certainly come a long way!

Shortly after the Sinclair station on the Old Route 66 trail, I crossed an old truss bridge that crossed over Johnson Creek in Spencer, Missouri. Like the old sections of Route 66 in Illinois, this section looked like an abandoned road going into the backwoods. It was beautiful.

Kansas only has a very short 13-mile section of the Old Route 66 path, and if you take that, you are blessed with crossing one of the few remaining Marsh Arch bridges left in the country – and the only remaining one on Route 66, this one having been built in the early 1900s.

Oklahoma likely has the most Route 66 sites of any state. After the road was decommissioned by the federal government for use as a federal highway, Oklahoma named it State Road 66. It’s easy to follow, although I did manage to miss a sign and ride maybe 50 miles off course. The best Route 66 Museum is in Clinton, Oklahoma. It covers the initial planning and construction of the route, along with different scenes of Americana, a video of the Dust Bowl, and more.

There are more giant statues to be seen as you pass through Oklahoma, including Buck Atom, the 21-foot-tall space cowboy in Tulsa holding a rocket. Tulsa also has a cool park downtown called the Cyrus Avery Centennial Plaza that has three tall old neon motel signs relocated there from the early days of Route 66. Further south is a Route 66 village with an old train, a gas station, and an oil derrick.

The last section of Route 66 I rode in Oklahoma was a mostly abandoned concrete road that paralleled Interstate 40, but you could tell it was part of the original route. How many mostly abandoned four-lane concrete highways going into nowhere with no traffic do you see? At one point, I thought I was off-track, but then I saw the Texas state sign and the familiar white outlined Route 66 logo painted on the road.

In Texas, much of Route 66 is access highways on either side of the interstate, which worked just fine for my trusty mule since I could travel at more relaxed speeds in the intense heat. Along the way, you pass by the Leaning (water) Tower of Britten in Groom, Texas, and Amarillo gives you the Cadillac Ranch.

After visiting the Cadillac Ranch, I stopped at a KOA, and when I tried to start my bike again, it didn’t fire up. It turned out to be an issue with the ignition system, and despite having the parts from my other SR500 shipped to me to attempt a repair, it didn’t take. I cut my trip short and loaded the bike in the back of a Penske truck and headed back east.

In spite of a flat tire, intense heat and humidity, and an ignition failure, this was the most fun I can recall in most of my life. In retrospect, I should have tried making this trip on a newer bike, but part of the fun was riding a kickstart antique.

If you are considering riding this road, I would suggest waiting until 2026 for the 100-year anniversary since I heard plans in various towns along the way for some centennial events, so it should be even better.

ROUTE 66 RESOURCES:

• National Park Service: Route 66
• Chicago Tourism
• Illinois Tourism
• Heritage Corridor (First 100 Miles of Route 66)
• Missouri Tourism
• Gateway Arch
• Oklahoma Tourism
• Texas Tourism

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