Unique Centennial Year Route 66 Guided Tour 2026

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 to kick-off your dream Route 66 journey!

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, stopping at the amazing RT 66 Museum in Pontiac and generally getting a feel for the rubber on the Mother Road.

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

Today we continue our ride through the heart of the Midwest, heading southwest across the Missouri Ozarks, a region famous for its rolling hills, lush forests, and Americana charm. You'll wind your way through vintage towns like Cuba and Devil’s Elbow, where time seems to have stood still since the heyday of Route 66. Stop in at quirky roadside attractions and classic diners that make this stretch one of the most nostalgic parts of the Mother Road. Tonight, we land in Springfield, Missouri – not to be confused with its Illinois counterpart – known as the “Birthplace of Route 66.”

Get ready for a ride full of classic Route 66 charm as we roll from Missouri into the great state of Oklahoma. Along the way, we’ll pass historic filling stations, vintage motels, and the iconic Rainbow Bridge in Riverton, Kansas—one of the last remaining Marsh Arch bridges on the route. As we enter Oklahoma, the wide prairies stretch out before us and the true spirit of Route 66 comes alive. We’ll ride through small towns like Miami and Claremore before rolling into Tulsa, a city where rich oil heritage meets vibrant Art Deco architecture.

Today is a special celebration of the road that brought us here – the 100th anniversary of Route 66! Tulsa, a city deeply intertwined with the history of the Mother Road, is hosting centennial events that bring together riders, classic cars, and fans from all around the globe. You'll have time to explore exhibitions, music performances, parades, and Route 66 landmarks. Whether it’s joining a commemorative group ride or simply soaking in the festive spirit, today is all about honoring a century of American road trip culture. Attending the festival is optional, giving riders the choice to join the festivities if they wish or explore Tulsa on their own terms.

Back in the saddle, we ride deeper into the heart of Oklahoma. Today’s route takes us through some of the most iconic and well-preserved parts of Route 66. We’ll pass through Sapulpa, Chandler, and Arcadia – home of the round red barn and the vibrant soda pop oasis, POPS. With its towering neon soda bottle out front, POPS is a must-stop for a cool drink and great photos. In the afternoon, we roll into Oklahoma City, where western heritage meets modern vibes. Be sure to explore Bricktown or visit the poignant Oklahoma City National Memorial.

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. We will offer an optional excursion to the Big Texan Steakhouse in Amarillo where you have the opportunity to enjoy the best steaks in Texas, guaranteed!

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.

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.

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.

From Gallup it’s only about half an hour to the Arizona border. Once you enter Arizona enjoy a very scenic ride through the Petrified Forest, a fossilized prehistoric forest of giant trees that has been unearthed by erosion. Just west of Petrified National Forest you get to Holbrook and Winslow, two old Route 66 towns that are kept alive by transcontinental truckers. Tonight we will stay in Flagstaff, the northern Arizona community on historic Route 66 and is the regions hub for visits to the Grand Canyon.

Today we ride one of the most legendary and scenic stretches of Route 66. Departing Flagstaff, we pass through Williams and make our way toward Seligman – the town credited with kicking off the Route 66 revival movement. Here you’ll feel like you’ve entered a living postcard of the 1950s, with retro diners, classic cars, and plenty of photo ops. From there, the route winds through the beautiful desert landscapes and mountain passes of northern Arizona, eventually descending into Kingman. This old railroad town is packed with Route 66 history and local character, making it a perfect stop for the night.

The California dream is getting closer. Today’s ride starts with a breathtaking journey through the Black Mountains on the twisting Oatman Highway, where wild burros roam free in the old mining town of Oatman. From there, we cruise down to the Mojave Desert, crossing the state line into California. We'll pass through dusty ghost towns and long-forgotten rest stops that hint at the golden days of the Mother Road. The heat of the desert gives way as we arrive in Victorville, once a booming stop for travelers headed west. Tonight marks our last night on Route 66 before reaching the Pacific.

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 at our Farewell Dinner!

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. See you next year!