Route 66: Discover Classic Americana
The price includes :
- Motorcycle rental
- Tour leader
The price doesn’t include :
Day 1 - Chicago
Our team will meet you at the airport and transfer you over to the hotel. Here we’ll enjoy a welcome drink and have a short tour briefing to discuss the itinerary and answer any questions you might have about the upcoming journey. Then we’ll enjoy dinner at one of our favorite spots in the Windy City. Are you ready for your Route 66 USA adventure?
Day 2 - Chicago- Springfield
We break out of the great city on our road trip USA by heading West on the I-55 which was built on top of the original Route 66. We’ll then cruise over to the “Pontiac Trail” of Route 66 getting away from the big highway and onto the classic roads that head towards Joliet and Wilmington. The turn-off will be easy to recognize by the “Gemini Giant” rocket-man statue that sits outside the famous Launching Pad Drive-In. We’ll zip over to Pontiac and stop at the RT 66 Museum to really inspire us for our incredible adventure. Here we’ll pick up the formal “Historic Route 66” that leads into Springfield Illinois—the home of Abraham Lincoln and the state capital.
Day 3 - Springfield
We’re diving into America’s heartland as we drive through miles of scenic cornfields and pass by charming small towns like Mt. Olive and Litchfield. By mid-day, we arrive in St. Louis and we’ll be greeted by the iconic 630 foot Gateway Arch. We’ll cross the mighty Mississippi over the Chain of Rocks Bridge and into the classic heart of St. Louis. We’ll enjoy a milkshake or sundae at Ted Drewe’s Frozen Custard—a Route 66 institution since 1941. We’ll then check into our hotel and have the rest of the day free to explore the great city along with its nightlife options.
Day 4 - St Louis - Carthage
Heading out from St. Louis, we’ll once again be riding the interstate built on top of the old Route 66 USA though there are still patches of it that run parallel to highway. There’s plenty of old school motels and other vintage charms of the past. Outside Stanton, we’ll stop to explore the Meramec Caverns. These stunning caves where once the hideout of famous outlaw Jesse James and also have their own underground river and beautiful rock formations. The drive becomes more exciting as we big to zigzag through the rolling hill country of the Missouri Ozarks arriving in Springfield, MO. In 1926, this was where RT 66 was birthed. We’ll enjoy a stop at Gay Parita’s Filling Station— a classic stop dedicated to the history of the “Mother Road.” We’ll then head over to Cartha where will spend the night in the famous Art Deco Boots Motel and maybe watch a movie at the 66 Drive-in Theater.
Day 5 - Carthage - Oklahoma
Leaving Carthage on our road trip USA, Route 66 dips very briefly in the southeast corner of Kansas— a tiny ten miles stretch. But this small section of Route 66 is proud of its Route 66 history. The main street of Galena is officially known as the “Kansas Route 66 Historic District” and is even decorated with a giant mural celebrating this heritage. From here, we’ll enter our longest uninterrupted stretch of classic Rt 66 which continues for more than 300 miles winding across the hills of Oklahoma and through towns like Miami, Vinita, and Afton. In Vinita, we’ll visit the Eastern Trails Museum—which describes the sad and important history of the “Trail of Tears” and the forced relocation of Native Americans to Oklahoma. We’ll then head over to Clanton’s Cafe to take a little break and enjoy the classic diner. Then we ride through the core of Rt. 66 Highway across Chandler and into Oklahoma City.
Day 6 - Oklahoma - Amarillo
We’ll leave Oklahoma City by crossing the iconic Overholser Bridge and ride a beautiful stretch of the classic highway to Hydro on our motorcycle tour USA. Here’ll we’ll enjoy a stop at Lucille’s Famous Rt. 66 built in 1929 to buy some souvenirs and take a break. We’ll then motorcycle along the old “Chisholm Trail” which crosses plains where massive herds of buffaloes once roamed. Today’s drive is lined with old motels and the town of Shamrock which is known for its classic Conoco Tower Gas Station. We’ll always by the sleepy town of Maclean which seems almost frozen in time and is headquarters of Texas’s Historic Route 66 Association. By late afternoon, we’ll arrive in the cattle town of Amarillo—formerly a major stop-off on the “Mother Road.” Here we’ll explore the Route 66 Historic District before enjoying dinner at the Big Texan Steak Ranch.
Day 7 - Amarillo - Santa Fe
We begin today by visiting the world-famous and eclectic Cadillac Ranch on our motorcycle tour USA. Here ten spray-painted vintage Cadillacs are half buried into the ground running along RT. 66. Just past here is Adrian and a marker celebrating the halfway point of Rt. 66. We’re now entering New Mexico and a 350 miles stretch of Rt 66 that’s like a time capsule from the past filled with classic Americana. Soon after we cross into the state, we’ll visit the incredible vintage car museum of Russell’s Truck and Travel Center before we slide by the retro Blue Swallow Motel. In Tucumcari, we’ll briefly leave the Mother Road at Clines to Corner to ascend into the rugged environment of mesas, cactus, and mountains to enjoy two days in Santa Fe.
Day 8 - Santa Fe
We’re going to give ourselves and our bikes some rest and enjoy this great city. Santa Fe is over 400 years old and known for its lively art and cultural scene and pueblo-style architecture. The town sits at over 6,000 feet in elevation with a simply perfect climate and stunningly blue skies.
Day 9 - Santa Fe - Gallup
In the morning, we’ll visit Los Alamos— the setting for the ultra-secret Manhattan Project during WWII where the world’s first atomic bombs were developed. We’ll discover some of this history before we descend the Sangre de Cristo Mountains and rejoin the Mother Road. We’ll pass through the large city Albuquerque before zooming over the Rio Grande and the majestic desert wilderness. We’ll spot ghost towns and incredible sandstone mesas and the farther off pine forests and sometimes snowcapped peaks. We’ll stop today at Laguna Pueblo, which has an early Spanish Mission as well as the incredible Acoma Pueblo, an ancient Native American pueblo carved into a mesa. By afternoon, we’ll reach Gallup and spend the night at the classic Hotel El Rancho. Here famous celebrities from the past like Gregory Peck, Ronald Reagan, and John Wayne all spent the night while crossing the country.
Day 10 - Gallup - Grand Canyon
As we leave Gallup, Route 66 is buried underneath the I-44 which will take us into Arizona and through the Petrified Forest National Park. This will by today’s first stop where we can marvel at these incredible ancient fossilized trees and marvel at the incredible scenery of the Painted Desert. We’ll push westward through Holbrook where we’ll see the famous Wigwam Motel from the 1950s. Then we’ll see the famous Meteor Crater, a giant crater formed from a meteor impact roughly 50,000 years ago.) We’ll then make a little diversion onto AR 89 where we’ll spend the night along the South Rim of the Grand Canyon.
Day 11 - Grand Canyon
The famous American Ron Swanson once wrote that crying was acceptable at only two places—funerals and the Grand Canyon. We’ll take the morning to explore some of this majestic natural site before we head back to RT 66. We’ll break away from I-44 and Rt.66, but still be on some classic roads that wind through the Hualapai Reservation through Peach Springs and Hackberry. When we arrive in Kingman, we’ll marvel at the Hoover Dam before enjoying a night in Las Vegas. Overnight at The Bellagio in Las Vegas.
Day 12 - Las Vegas - Victorville
We’ll continue our Route 66 USA adventure in the old gold-mining town of Searchlight. We’ll drive today through the breathtaking heart of the Mojave Desert. Zooming along on our motorcycles will give us a taste of what it must have been like to travel through here in the days before air conditioning and airplanes. Along the way, we’ll enjoy a break at the 1950s Roy’s Motel Cafe & Gas Station in Amboy. Near here, we’ll even explore some lava flows and volcanic flows by hiking up Amboy Crater if it is not too hot out. Then we’ll ride into Barstow and into the perfectly preserved 36-miles stretch of “Old Route 66.” We’ll take some photographs at Elmer’s Bottle Tree Ranch before heading into Victorville and exploring the California Route 66 Museum.
Day 13 - Victorville - Santa Monica
We’ll follow along the final laps of the old Route 66 that run nearly parallel to massive I-15 Interstate Highway. We’ll descend quickly through Cajon and into the endless urban sprawl of the San Gabriel Valley. Don’t worry, we’ll escape this by riding along the Angeles Crest Highway, one of the most beautiful motorcycle rides in all of California that runs through the San Gabriel Mountains. These we’ll drop us down into the charming city of Pasadena where we’ll join Historic Route 66 once last time as we wrap up our journey at the Santa Monica Pier and the famous “End of the Trail” sign. In Santa Monica, we’ll enjoy a celebratory dinner to toast our accomplishments on this great motorcycle tour USA we’ve had.
Day 14 - Santa Monica - Los Angeles
It’s time to wrap up our great adventure. After breakfast, we’ll transfer you over to the Los Angeles International Airport where you can head home. If you are looking for more adventure ideas, we’re here to help you plan your next great trip!