How to Rent Route 66 by Motorcycle, Part 1

America is awesome. But it’s huge. Do you want to spend days riding through all of it to get to the good parts? What if you just want to ride in one awesome place, ride through other awesome places, then just go home? Enter EagleRider Motorcycle Rentals and Tours.

Sure, it’s fun to take mechanically suspect used motorcycles and travel long distances to prove your man- or womanhood. But then you get older and/or wiser. You get a van or trailer and just drive to the good parts. Then you get even wiser, which is where the motorcycle rental part comes in.

In the spirit of full journalistic disclosure, EagleRider gave Motorcyclist a Club membership with 18 credits to ride wherever somebody from Motorcyclist wanted. I volunteered to be that somebody. In return, I offered to write an honest account of whatever the hell I felt like.

First, a little background. EagleRider started renting new motorcycles to touring enthusiasts in 1994 and currently has 200 locations in 30 countries worldwide. There are 26 North American guided tour options and 60 self-guided tour options, complete with an app that highlights Instagram-worthy points of interest. The company tailors packages around events like Harley-Davidson’s 120th anniversary or Sturgis, in addition to regional tour themes like “Wine Country” or “The Civil War.”

A self-guided eight-day Chicago to Albuquerque tour starts at $1,600, while the 15-day Chicago to LA version starts at $2,816. I made up my own Route 66 tour starting in Chicago and returning eight days later. I have no idea how far I’ll make it. Technically, I’m taking a self-guided tour, complete with hotel accommodations and itinerary, courtesy of EagleRider. A self-guided tour works for me since I’m a loner. Just like PeeWee Herman in the movie, PeeWee’s Big Adventure.

The listed prices are for Club EagleRider members. There are three levels of membership: $29, $55, and $79, which earn you one to three credits per month, which can be applied toward rentals or tour offerings. Club members also get deeply discounted rates on rentals. It’s basically a subscription model. The idea is to offer the ride without the hassle of ownership, transport, or cleaning bugs off windshields.

I download the app, log in to my complimentary Club membership, and begin choosing which bike I want. The Yamaha Ténéré 1200 probably has heated grips. Sold American.

So what’s the experience like? Time to find out.

Renting motorcycles is all about convenience and ease. But I choose the hard way to see the USA. I’m leaving Chicago on a rainy, 40-degree-Fahrenheit April Fools’ Day. Arriving early at EagleRider General Manager Danny Brown’s Chicago location, I am the first customer of 2023.

Dozens of gleaming Harley-Davidsons, BMWs, Yamahas, and even a few Royal Enfields grace his spotless shop. Everything you could possibly need (or have forgotten) is available for sale. Cargo nets, farkles, leather vests with patches, and even chapstick. Danny gives me a safety and operational briefing on my Ténéré 1200, gives me papers to sign, and I’m off.

“Hey, what if I decide to change my itinerary?” I ask.

“Just let me know as soon as possible,” Danny says.

He gives me a card with his personal cell number and tells me to call him if I need anything. If anything happens with the bike, call him. If tire pressure is low, call him. He has no idea I’m writing about this and got tons of expensive stuff for free. Danny, you’re a mensch.

Of course Route 66 starts in Chicago. Historically, it’s one of America’s best places to leave. EagleRider’s app offers an itinerary and map, which doesn’t actually include the famous starting point of Route 66 in Grant Park. So I head downtown, take a pic, and I’m off. The original route goes through dicey areas of Chicago’s Ogden Avenue. But it’s raining so I take I-55. No wonder I’m leaving you, Chicago.

The EagleRider route hits the old Route 66 in Gardner, Illinois, where I-55 shadows it to Springfield. Both roads are often within sight of each other. I’m free to pick and choose between quaint and quick travel. But it often splits away into towns like Dwight, Towanda, and Pontiac. Here, you can see abandoned portions of the pre–World War II Route 66, overgrown with weeds. The EagleRider app is coming in handy, but not for navigating. It shows where you are with nicely curated points of interest, but you can’t actively navigate with it. According to SVP of Strategic Growth and Marketing Shawn Fechter, turn-by-turn navigation with voice prompts are coming later this year. Stay tuned.

The suggested-stops part sounds basic, but Route 66 is 2,400 miles long. You’ll need help finding all of America’s hidden cultural treasures. And it clearly shows where Route 66 goes, even when local signage and Google Maps doesn’t. If left open with Google Maps on, it eats battery life, so maybe just open as needed. But you’ve got your $6 USB power adapter, right?

Springfield is great, but unless there’s a state fair or flat-track racing, it’s a sleepy town bordering on narcoleptic. Standing 30 stories above everything else is the round, Soviet-looking Wyndham hotel, the nicest in town. My EagleRider tour comes with Best Western accommodations in each of the assigned stops. But I pony up for the chance to survey the flatness of Illinois from a Brutalist 28th floor lair.

The next day, I’m set on escaping Illinois. But there’s great Route 66 heritage, and each town is worth a stop. Although not on the EagleRider map, Route 4 just north of Auburn, features a 1.4-mile long brick road. Better than the yellow brick road, it’s made of actual red brick, part of the US 66 road alignment in 1926. From there, signs show “Route 66 Byways.” But these signs are made of lies. A byway is not actually Route 66. Charming all the same, though.

Other Route 66 byways feature ancient concrete slab farm roads. These likely predate the initial 1926–30 US Route 66 construction. In 1916, the Federal Aid Road Act began improving existing farm roads which were vital for the rural Midwest economy. By today’s standards, they’re barely golf cart paths. But they’re a good test for the Ténéré's suspension.

Route 4 in Illinois meets up with I-55 again, and it’s slab time again. The EagleRider route suggests Route 157. But I’m making miles, so I hit I-270 into north St. Louis. St. Louis is the biggest city the EagleRider tour goes through. It’s also one of the most challenged, economically speaking. But kudos to EagleRider; the app follows the correct Route 66, right alongside the defunct Chain of Rocks Bridge and onto Bellefontaine Road.

The EagleRider route suggests taking I-70, but you should take Broadway Street to downtown. Every American city’s fortunes rise and fall, and St. Louis is no exception. You’ll see America’s past manufacturing glory and decline in red brick and abandonment. Plywood windows and majestic abandoned factories go on for miles, with concrete dividers placed perpendicular to the street to discourage drag racing. Non-plated dirt bikes and four-wheelers take advantage of this unofficial autonomous zone. They’ll give you a rider’s wave, regardless. This goes on until downtown, where the arch awaits.

Plug in the arch to Google Maps, and it takes you down the old Route 66 to Chouteau Avenue, past yet another dark industrial area leading to the waterfront. And then to $10 parking. Let’s see what else Missouri has to offer. Hey, Rolla, Missouri, exists. Let’s go there.

Missouri’s old Route 66 shadows I-44. It’s easy to squint and enjoy the lazy two-lane while ignoring the giant interstate on your left or right. You see small-town America up close. Missouri is proud of its Route 66 heritage. Generous signage greets you at every junction and every town displays a mural of the town’s attributes, with a big Route 66 logo.

The EagleRider tour nests for the night at the Best Western Coachlight, conveniently next to the Tater Patch Pub & Grill. I talk to a nice guy who looks like Karl Marx or Mark Twain. We’re close to the Mark Twain National Forest, so maybe more the latter.

“Where you headed?” he asks.

“As far as I can make it on Route 66 before I gotta head back,” I reply.

“So you’re just going to see the beginning twice?”

Good point, Mr. Twain. Walking back to the hotel, I find a unicorn sticker on the ground and put it on the right pannier, likely breaking an EagleRider rule. But it’s a road rule. If you don’t get a sticker for going somewhere, did you really go there?

Southwest Missouri has lots of extant Route 66. Exiting at Devils Elbow, I ride all the way to (yet another) Springfield. The EagleRider app highlights a place called Red Oak II, north of Carthage. The original Red Oak existed 18 miles northwest of Red Oak II. Former resident Lowell Davis returned to his birthplace in the 1970s and discovered it abandoned. So he spent years acquiring the buildings and property and moving them to the newly (re)created Red Oak II. It’s a Potemkin village of America’s past, but beautiful all the same.

Missouri ends on a high note. What’s Oklahoma’s Route 66 like? No state has more Route 66 miles than Oklahoma. Oklahomans—to the tune of 60,000—used Route 66 to leave during the Dust Bowl. Departing from the EagleRider itinerary, I pick the biggest, boringest, and (presumably) cleanest hotel outside of Tulsa to rest and recharge. Turns out I’ll need it.

These are the toughest miles of the trip. A wind advisory brings 25–40 mph winds. These winds stir up soil, dust, and anything unlucky enough to stand in its way. The resulting swirl dims the sun. What sort of god would create a place like this?

Stopping brings relief. The Rock Café in Stroud, inspired a character in the Pixar movie Cars, and has amazing fried green tomatoes. And the Round Barn in Arcadia, is a fine example of one Okie’s ingenious attempt at tornado-proofing barns. The Oklahoma Route 66 Museum in Clinton lets me sneak in 10 minutes before closing and lets me out when I’m done. Oklahoma’s hospitality is second to none.

How’s life aboard the Ténéré 1200? It’s awesome because it’s not mine. I don’t think about the oil, tire pressure, or hundreds of bug carcasses covering it. If something bad happens, I’ll call Danny. Until then, I just fill it with gas whenever the gauge starts blinking.

Whatever suspension setting it came with is great, so I leave it alone. The Ténéré probably does a bunch of things I don’t know about. But it shows trip duration so I know when I’ve earned a stop. I seldom use cruise control, but it helps with arm-and-hand stretching. It gets around 43 mpg, but mostly I’m obsessed with mileage totals.

I give up fighting the wind at the 275-mile mark in Elk City. I’ve experienced all of Oklahoma at a 5–10-degree angle, regardless which way I’m turning. How much more of this state is there? Near Bristow, I almost have to call Danny. The Ténéré gets stuck in a muddy ditch after I ride onto an abandoned portion of Route 66. But it eventually breaks free. Technically, you’re not supposed to go off-road on the Ténéré but that Instagram pic was really important. Sorry, EagleRider.

The actual tour takes 15 days and 14 nights. But I’ve got eight days and a dream; to see the Cadillac Ranch outside Amarillo, Texas. Wind notwithstanding, I’m enjoying the hell out of the experience. I don’t want to see what I saw again from the opposite lane.

I text Danny to see if I can drop off the Ténéré in Las Vegas instead of Chicago. Not a problem, he says. Flexibility when traveling solo matters. I owe you a beer, Danny. In the wise words of AC/DC, put the champagne on ice, I’m going to Sin City.

Coming in Part 2: Texas, New Mexico, Arizona, Nevada, and a tiny bit of California.