© 2025 Susy Travel all rights reserved
USA on the road by motorcycle... beyond Route 66
A road trip to discover the American wonders aboard a Harley Davidson.
This trip was organized as a gift for my husband's 40th birthday.
Since he is a motorcyclist, the surprise for this milestone could only be a road trip, in the USA and aboard a splendid, brand new Harley Davidson.
For a true biker, this itinerary is a bit of the American dream as it winds through the most authentic wonders, on roads often deserted with breathtaking views.
The itinerary includes: 23 days of travel, 18 stops, 17 states crossed, and 5,700 miles (that is, 9,200 km.)
It is a demanding trip as you spend a lot of time on the bike. Consider that you will often arrive at the end of the day rushing to dinner (in the USA people dine early) without even having time to shower first. But I assure you it is really worth it. This trip will forever remain among our most beautiful memories!
Here is, below, the travel story.
- Chicago (Illinois)
- Milwaukee (Wisconsin)
- Green Bay (Wisconsin)
- Treampealeau (Wisconsin)
- Vermillion (South Dakota)
- Rapid City (South Dakota)
- Buffalo (South Dakota)
- Cody (Wyoming)
- Craig (Colorado)
- Ouray (Colorado)
- Monument Valley (Utah/Arizona)
- Madrid (New Mexico)
- Alamogordo (New Mexico)
- Amarillo (Texas)
- Oklahoma (Oklahoma)
- Clarksdale (Mississippi)
- Memphis (Tennessee)
- Nashville (Tennessee)
- Springfiled (Illinois)
- Chicago (Illinois)
I imagine that many of these cities mean nothing to you... As you continue reading the details of each stage, you will find all the answers and see what wonders are hidden behind these names, for now, mostly unknown to you.
Let's start with the itinerary:
CHICAGO
We finally land at Chicago airport. With our small luggage (remember, this is a motorcycle road trip... later on you’ll find all the details on how to organize your luggage) we head to the hotel. Tired from the journey and with our lovely jet lag, we jump in the shower and get ready for an American style dinner, not too heavy because tomorrow is the big day! After a quick breakfast with coffee and a snack at the hotel’s coffee shop, we take a taxi and have ourselves dropped off at Eagle Rider (below you’ll find a dedicated section with all the info for motorcycle rental). Once we arrive, we find an unspecified number of Harleys parked along the entire street, just waiting to be started up for a new adventure. We go inside and start dealing with the rental paperwork. The Eagle Rider guys already look like real bikers: beards and long hair with bandanas, rings, tattoos, but very kind and helpful. While all the documents are being signed, your eyes wander around the shop: there are tons of motorcycle accessories and countless clothing items. We bought some amazing helmets for a negligible price, thus avoiding having to wear the rental one. Once the paperwork is done, they take us to our bike. With great excitement, we meet our travel companion. They briefly show us how it works, the warning lights, etc... and we’re finally ready!
Tip: to get familiar with the bike, before setting off, it’s a good idea to take a ride around the block.
MILWAUKEE
After leaving Chicago, we head towards Milwaukee: the birthplace of Harley Davidson, to which a large museum is dedicated.
Milwaukee is also commonly known for the TV series Happy Days, which was "supposedly" set in this city. In fact, all the episodes were filmed in a studio and not a single scene was shot in Milwaukee. Of Happy Days, the memory remains through the so-called Bronze Fonz: the bronze statue of the legendary Fonzie.
Milwaukee is a very unique city, a real melting pot where Afro ghettos, mosques, and Victorian villas coexist.
GREEN BAY
We leave Milwaukee and head towards Green Bay, the city of the American football team Green Bay Packers.
I assure you that, even if you are not a fan of this game, it is definitely worth visiting this team's stadium and seeing with your own eyes what and how much lies behind this sport.
TREAMPEALEAU
We cross Wisconsin, skirt Lake Winnebago and pass through La Crosse until we reach the small
town of Treampealeau, directly overlooking the Mississippi River, where the hospitality is in perfect American style.
VERMILLION
This will mainly be a transfer stage to reach South Dakota.
From Treampealeau we will cross beautiful countryside landscapes until we reach Vermilion.
RAPID CITY
MOUNT RUSHMORE & BADLANDS
We leave Vermilion to head towards Rapid City where we will finally visit the legendary Mount Rushmore. Along the way, we experienced one of the worst rainy days of our motorcycling career: we were soaked from head to toe. Having lunch inside the rest stop with the air conditioning blasting at full power didn't help. Fortunately, we had a change of clothes so we could put on something dry. After all, real bikers face all difficulties. Continuing towards the Badlands, the weather changed completely... finally sun and warmth, and what a view!
BUFFALO
From the Black Hills we make another transfer stop to enter Wyoming at Buffalo, to get closer to Cody, the gateway to Yellowstone Park.
CODY
Memorable stage of this tour. We leave Buffalo to head towards the town of Cody, passing through the Beartooth Highway, ranked as number 1 in the ranking of the most beautiful roads in America: a mountain pass with spectacular views. From Cody we will enter the Yellowstone park where we can contemplate all the natural wonders of this immense park. In the evening, after a dinner in perfect country style, we will attend the Rodeo. Upon your arrival in Cody, pay attention: deer roam freely through the streets of the city and often sneak into the gardens of houses in search of food.
CRAIG
We leave the wonderful Wyoming passing through Shoshoni Park. This will be a transfer stage to enter Colorado and get closer to Monument Valley, passing through enchanting American landscapes.
OURAY
We leave Craig to head towards Ouray and enter the lands of the great Ranches that you may have often heard mentioned in the series The Ranch starring Ashton Kutcher. To reach Ouray we will pass through the Grand Mesa National Forest, the largest flat-topped mountain in the world, where we will witness a wonderful show of nature. Along the way I recommend stopping for a break in the town of Montrose: a small, very folkloric town with charming little shops and diners along the main street. Scattered throughout the town you will find bales of hay. The photo of the cowboy below explains the reason for all this hay...
The town of Ouray is a fairly popular mountain tourist destination. All the hotels are very characteristic and stylish. Being in the mountains, the weather is quite variable as you can see from the photo below...
MONUMENT VALLEY
We leave Ouray and travel along the splendid Million Dollar Highway, one of the most beautiful scenic roads in the USA, down to Durango, passing through Bluff until we reach the entrance to the magnificent Monument Valley.
The stretch from Ouray to Monument Valley is quite long, but just as fabulous in terms of scenery and nature. For this reason, the route deserves a thorough description, which you can find on the detailed page below.
FOUR CORNERS MONUMENT
The next stage towards New Mexico will be quite long. Since it's on the way, a stop to visit the Four Corners Monument is a must. This is a monument located at the only point where the borders of Utah, Colorado, Arizona, and New Mexico meet, in the center of the region called Four Corners.
MADRID
We leave the Four Corners Monument to head towards the spectacular New Mexico. The first stop in the Land of Enchantment (New Mexico is indeed called the Land of Enchantment... you will find it written on all the license plates) will be Madrid... an unmissable stop if you are true bikers. Do you remember this small town? You have definitely seen it in a famous movie starring, among others, John Travolta......
ALAMOGORDO
We leave the hippie community of Madrid to continue our journey through New Mexico. To immerse yourself in a typically American atmosphere, stop for lunch at Carizozo at the Four Winds Restaurant and take a seat at the counter. Once again, the weather was not very kind: we ran into a storm with sand whirlwinds rising from the fields next to the road. Fortunately, once the storm passed, it allowed us to arrive at our destination with the sun....and what a destination!!
AMARILLO
We cross the border into New Mexico and enter Texas. You will immediately know you have entered this state by the black masses you will see in the distance... these are the typical Texas cattle ranches. This stop will take you onto the famous Route 66 which passes through the city of Amarillo. Here you can immerse yourself in the typical Texan atmosphere made of cowboys, ranches, and huge steaks!
ROSWELL
Before leaving New Mexico and entering Texas, we make a stop in Roswell: a town made famous by the so-called Roswell incident that happened here on July 2, 1947, when an unidentified object crashed to the ground. The event quickly became a scoop as the first news reports speculated that one or more UFOs had crashed, and according to some theories, this was followed by the alleged recovery of extraterrestrial bodies by the US military. Today, Roswell still lives off the fame of this incident: you will in fact find numerous shops and museums with an extraterrestrial theme.
OKLAHOMA
We leave Texas and enter Oklahoma. This will just be a transfer. For our trip, we hadn't planned anything for this stop, relying completely on chance. So we stayed overnight at a pleasant motel, had dinner at a fast food restaurant, and had breakfast at a gas station. The most exciting thing about this stop (Oklahoma doesn't offer much from a tourist point of view) was riding a motorcycle, even if only for a very short stretch, without a helmet. Here, in fact, the helmet is not mandatory but it's always good to pay attention!
CLARKSDALE
Having left Oklahoma, we head swiftly towards Mississippi, passing through Arkansas. The journey will lead us to discover the immense river and the picturesque villages of its delta. Clarksdale, in particular, capital of the blues where we can attend an unusual live music show....
MEMPHIS
From Clarksdale, it's a must to take a trip to Memphis to Graceland: the monumental museum house of the legendary Elvis Presley! And along the way, don't miss the chance to buy and taste some boiled peanuts: boiled peanuts that you will find only here...
NASHVILLE
We leave Mississippi and enter Tennessee to reach Nashville: the capital of country music. Here we can wander around honky-tonk bars, drink some local Jack Daniel's, dance a bit of line dance and buy boots for a few dollars...
SPRINGFIELD
In Nashville, hurricaneHarvey is passing through and on the day of our departure here we are under the incessant and heavy rain left by the tail of the hurricane. What a trip!! In the end, we managed to leave Tennessee and enter Illinois: the last state that will be touched by our tour.
CHICAGO
We leave Springfield and head towards Chicago where we will leave our travel companion and then continue visiting this beautiful city that will have so much to offer us!
LAST BUT NOT LEAST.....
how to organize your luggage for a motorcycle trip!
And here we are, as promised, at the long-awaited chapter on how to organize the luggage for our 3-week motorcycle trip.
© 2025 Susy Travel all rights reserved