Route 66 Motorcycle Tour™

Guided Tour 15 Days / 14 Nights
Tour Map
  • 2807.0 mi = 4491.2 km
  • Summer, Spring, Fall
  • 55.0 - 105.0°F = 12.8 - 40.6°C

EagleRider's World famous Route 66 motorcycle tour travels the original Route 66, known as the "Mainstreet of America" or "Mother Road" . At over 2400 miles long from Chicago to Los Angeles, Route 66 crosses three time zones and 8 States: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Route 66 has been the path of migrants, dreamers, desperadoes and an entire generation of vacationers discovering the way west. The 1950's were the Route 66 glory days, when thousands of cars rode bumper to bumper behind each other to experience the Western frontier. Hotels, motels, gas stations, classic restaurants, and the "New" America sprang up everywhere. Much of Route 66's classic roads, restaurants, gas stations, and nostalgic landmarks are preserved just as they were in the 1950’s. The famous and nostalgic Route 66 is the road created in heaven for motorcycle touring. Simply stated, this is the guided tour of America!

Tour Itinerary

Welcome to the Windy City! Nicknamed the 'Paris of the Prairie', Chicago is the biggest and most exciting of the Great Lake cities. It includes a stunning skyline along Lake Michigan, and a gamut of top-rated museums, restaurants and cafes, and innumerable bars and nightclubs that pay homage to the city’s strong jazz and blues heritage. Tonight you will get to meet your fellow riders and Tour Guides at an Orientation Meeting at the tour hotel, followed by a great Welcome Dinner and celebration downtown. Your dream Route 66 journey is about to begin!

Learn more about this tour from Shawn, EagleRider VP of Tours:

This morning you pick up your bike and are off to the ultimate American road trip. The legendary Route 66 begins at the doorstep of our EagleRider location, cutting through the state of Illinois before running all the way to the Pacific Coast. From Chicago you head south along the Pontiac Trail, the original name for this bit of the road here, passing through Joliet, checking out the Launching Pad Giant, stopping at the amazing RT 66 Museum in Pontiac and generally getting a feel for the rubber on the Mother Road.

Learn more about this tour from Ken, EagleRider Manager of Tours:

Today we head towards St. Louis! We will stay primarily on the 2-lane sections of the Mother Road, traversing cornfields and small towns that represent the heartland of America. Our arrival into St. Louis will be over the Chain of Rocks Bridge, the original bridge where RT 66 crossed the Mississippi River. Enjoy the short ride today into the "Gateway to the West," St. Louis. This amazing city rests along the shores of the mighty Mississippi River and is home to some of the best live music and BBQ ribs in the country.

Learn more about this tour from Ken, EagleRider Manager of Tours:

Try to get up early to walk across the street today and enjoy an early morning view of the St. Louis Arch and Mississippi River before we hit the road. We quickly leave the city in mirrors as we settle in to enjoy the rolling Missouri hills that make this area so beautiful and fun to ride in. We will stop and see the famous World’s Largest Rocking Chair in Fanning, wind our way on the twisting roads of Devil’s Elbow, and stop at other Route 66 icons. Tonight we will enjoy a stay in Joplin, a city that was hit very hard in 2011 by a massive tornado. Maybe tonight we'll hang with the locals and hear some amazing stories about what it was like to be in the eye of a massive tornado!

Learn more about this tour from Shawn, EagleRider VP of Tours:

Today is all about the route! From Joplin we will head west through the hills and horse country through Oklahoma, crossing Miami, Claremore and Catoosa, home of the legendary Blue Whale before passing through Tulsa, We will also go through the reservations of several Native American tribes. In the 1830s, much of this land was considered "unusable" by the Federal Government, so various Indian tribes were "settled" there after colonization, including the Choctaw, Chickasaw, Seminole, Creek and Cherokee. This evening we will stay in Oklahoma City, the heart and soul of Route 66.! At night you can enjoy at Bricktown, the neighborhood in the heart of the city full of lively restaurants, bars and shops.
This morning we travel along some of the oldest stretches of Oklahoma’s Route 66. Once the land of vast buffalo herds, this section of 66 traverses some of the great cattle trails which were used in the 1860s to drive herds of cattle from Texas up to the railhead in Abilene, Kansas. We will ride along a section of the Chisholm Trial, which passes through Yukon and El Reno, and stop at the amazing Route 66 Museum in Clinton. After lunch we cross the border into the Texas Panhandle, the southernmost portion of the Great Plains. Once in Amarillo, our good friends from "The Big Texan Steakhouse" will pick our group up at the hotel in a fleet of old Caddies graced with the horns of Texas Longhorns across the hood and take us to enjoy the absolute best steaks in Texas!

Learn more about this tour from Steve, EagleRider Tour Guide:

Today you leave Texas and are on your way into “The Land of Enchantment”, New Mexico. After passing through the world famous Cadillac Ranch, we'll stop at the midway point of RT 66 in Adrian, Texas! And how about the ghost town of Glen Rio, where you can stand with one foot in New Mexico and the other one in Texas? From there we enter the land of the Comanche Indians, where mesas, mountains, cactus and pines define the landscape as we head up into the High Plains and altitude of Santa Fe in central New Mexico. Santa Fe is one of America’s oldest and most beautiful cities, and will be our base for the next two nights.

Learn more about this tour from Shawn, EagleRider VP of Tours:

Today is at leisure to rest and enjoy the distinctive flavor of this nearly 400-year-old city. The blend of cultures here becomes evident in the southwestern architectural style so closely associated with New Mexico’s capital city. Perhaps you would like to take a ride along the river valley to the old Native American Indian town of Taos, enjoy a sunrise hot air balloon ride, or play cowboy for a day on a horseback ride along a mountain or canyon trail. Santa Fe provides all of these opportunities and more.

Learn more about this tour from Stefano, EagleRider Tour Guide:

This morning you head south, down to Albuquerque, New Mexico’s largest city, with a third of the state’s population. Albuquerque is sprawling at the heart of New Mexico, where the main east - west road and rail routes cross both the Rio Grande and the old road south to Mexico. You cross the Rio Grande and head west – out into the open country and the hues of the Navajo wilderness. You are skirting mesas and bluffs on into Laguna. Further on ride through Grants and along Cibola National Forest towards the famous Route 66 town of Gallup – an old railroad town and Indian stronghold. Enjoy your stay tonight with a host of fellow riders from around the world at one of the many biker friendly hotels in Gallup.

Learn more about this tour from Erik, EagleRider Director of Business Development:

Today is another huge day, full of spectacular scenery and iconic Route 66 stops. We cross the border into Arizona and ride to Petrified Forest National Park, a fossilized prehistoric forest of gigantic trees that has been unearthed by erosion. Here you will have the time to explore this stunning landscape and take a moment to get lost in the expansiveness that defines this area. Leaving Petrified Forest NP, we travel further west to the Wigwam Hotel in Holbrook, and stop to stand on the corner in Winslow! While most groups stop in Flagstaff or Williams, Arizona, we will ride on to spend our night just one mile from the South Rim of the Grand Canyon! Tonight you will sit with a cold drink in your hand and enjoy the sunset over the South Rim of the Grand Canyon. The dream is coming true!

Learn more about this tour from Shawn, EagleRider VP of Tours:

For those looking to get a real "Bird's Eye View" of the Grand Canyon be sure to let us know and we will arrange a morning helicopter ride over the heart of the South Rim. Leaving the Grand Canyon, we will pick Route 66 back up in Williams, Arizona before heading to stops in the famous 66 towns of Seligman, Hackberry and Kingman, and Oatman before arriving at our Laughlin hotel on the shores of the Colorado River..

Learn more about this tour from Stefano, EagleRider Tour Guide:

Today is a quick ride for a little detour to take in the incredible sights and sounds of Las Vegas! Our journey this morning will take us through our first real taste of the Mojave Desert, and a ride across the famous Hoover Dam! One thing is for sure, your time in Vegas may be short, but it will sure be sweet! Try to get a little bit of sleep because we pick up Route 66 tomorrow right where we left off yesterday.

Learn more about this tour from Ken, EagleRider Manager of Tours:

Today we cross the border into our final State on Route 66 – California! One thing is for sure - today is a day like no other as we traverse the Mojave Desert which offers some of the most dramatic scenery in Southern California. You can imagine what it must have been like for early Route 66 travelers making their way across this huge expanse of desert, dotted with Joshua Trees, cactus, volcanic rock and sand as you stop in the tiny "waystations" of Amboy and Ludlow. Tonight, we celebrate our last night on the Mother Road.

Learn more about this tour from Erik, EagleRider Director of Business Development:

Today we head off for our final destination – the end of the road on the Santa Monica Pier! To get there, however, we first get to ride the 66 miles of the Angeles Crest Highway through the mountainous terrain of Angeles National Forest. This highway is considered one of the top motorcycle rides in southern California and rises to over 2300 meters. Next we descend the Crest into the Los Angeles Basin and head towards the Pacific Ocean. Riders always have mixed emotions as they stand at the "End of the Trail" sign on the Santa Monica Pier. There is a sense of joy and elation at having completed a journey most people only dream about, and a sense of sadness at the thought of the ride having come to an end. Tonight we celebrate the miles we’ve ridden and the friends we made as we party together for our Farewell Dinner!

Learn more about this tour from Ken, EagleRider Manager of Tours:

Today your exciting trip will conclude in Los Angeles. Please be sure to let us know if you need an extra night or two in L.A. to enjoy the sights. We can even arrange a discounted motorcycle rental! See you next year! EagleRider

Learn more about this tour from Erik, EagleRider Director of Business Development:

68 User Reviews (VIEW ALL) ADD REVIEW
Andy Cliss November 24, 2018 10:32 pm

Route 66 20/10/2018 to 04/11/2018

No words can explain the emotions experienced during our Route 66 guided tour in September. Truly an experience of a lifetime. We had researched the trip in detail prior to leaving & thought we were prepared, however I don't think anything could have braced us for what was ahead. From our first contact with our tour leader Richard Wynkoop & his support driver Shane Porter we felt their immense passion for what they do & their commitment to ensure everyone in the tour group was looked after.
Once on the road the other tour members quickly bonded & within days we felt as though we were riding with friends we had known for years, sharing the adventure & laughter with people more like family than ones we had met only days earlier. The accommodation was mostly without fault, the bikes were all current models & they performed as expected.
Thank you both Richard & Shane for your leadership, your organisational skills & for sharing with us your vast knowledge of the “Mother Road”. You really did make this an adventure that we will never forget.

Andy & Gai
Wollongong, Australia.

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Peter Lane November 18, 2018 10:09 pm

Would happily do it again!

Tour Date 30th August 2018.

We met Buddy Guy at his bar and thought that could be the highlight of the trip. We were wrong!

The tour got better and better as each day rolled on.

Helped, undoubtedly, by a great group of people, but the sights, sounds and characters of Route 66 made it.

Accommodation was top notch and the riding was terrific.

Angeles Crest will remain with me for a long time.

The absolute highlight of the trip was our tour guide Richard Wynkoop. Ably assisted by Patrick in the support vehicle.

Without Richards experience and local knowledge, the trip would have been good, but not great. His relationships with the people of Route 66 somehow added a personal touch to the tour.

We had a ball and will be back to do Sturgis in the near future.

Pete and Cath Lane

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