Route 66 Anniversary Tour for 66 Bikers
Eaglerider Route 66 Centennial Tour  

Chicago – Los Angeles

Join us on the once-in-a-lifetime Route 66 Centennial Tour – a 15-day adventure filled with unforgettable experiences to celebrate 100 years of America's most iconic road. From the impressive Chicago skyline to the sun-drenched Santa Monica Pier, you'll drive right through the heart of the country on the original "Mother Road."

Experience the charm of small towns, legendary roadside attractions, historic landmarks, and breathtaking scenery as you roll through eight states and countless stories. This tour is more than just a drive – it's a tribute to freedom, friendship and a century of unforgettable road trips.

Arrival in Chicago – Arrival
0 miles / 0 km

Welcome to the "Windy City"! Chicago, also known as the "Paris of the Prairie," is the largest and most exciting city in the Great Lakes region. Here you can expect an impressive skyline along Lake Michigan, world-class museums, restaurants, cafes and bars that celebrate the city's jazz and blues tradition. Tonight, you'll meet your fellow travelers and guides at an orientation meeting, followed by a welcome dinner to kick off your Route 66 dream trip.

Day 2 – Chicago – Springfield, IL
203 miles / 325 km

Today you pick up your motorcycle and start your ultimate American road trip. The legendary Route 66 begins right outside the door of our EagleRider location in Chicago and takes you south along the Pontiac Trail, the original name of this section, through Joliet with a stop at the impressive Route 66 Museum in Pontiac. Here you get your first feel for the asphalt of „Mother Road“.

Day 3 – Springfield, IL – St. Louis, MO
92 miles / 147 km

Today we continue towards St. Louis! You'll drive along the two-lane sections of Route 66, through cornfields and small towns that embody the heart of America. The approach to St. Louis is via the historic Chain of Rocks Bridge, the original bridge of Route 66 over the Mississippi River. Enjoy the short drive to the "Gateway to the West", known for live music and legendary BBQ ribs.

Day 4 – St. Louis, MO – Springfield, MO
216 miles / 346 km

You'll drive through the rolling hills and forests of the Missouri Ozarks, a region full of nostalgic Americana charm. Along the way, you'll wind your way through towns like Cuba and Devil's Elbow, where time seems to stand still. Along the way, quirky roadside attractions and classic diners invite you to stop. In the evening, arrive in Springfield, Missouri – known as the "birthplace of Route 66."

Day 5 – Springfield, MO – Tulsa, OK
181 miles / 290 km

Get ready for a stage full of classic Route 66 charm. Drive from Missouri to the state of Oklahoma, passing historic gas stations, nostalgic motels, and the iconic Rainbow Bridge in Riverton, Kansas – one of the last surviving Marsh arch bridges. As soon as you enter Oklahoma, the landscape opens up to vast prairies, and the spirit of Route 66 awakens. Stops in Miami and Claremore round out your day before reaching Tulsa, known for its Art Deco architecture and oil history.

Day 6 – Tulsa – Route 66 Anniversary Events
0 miles / 0 km

Today is a highlight: 100 years of Route 66! Tulsa, closely linked to the history of the Mother Road, hosts events that bring together bikers, classic cars and fans from all over the world. You'll have time for exhibitions, parades, live music, and the city's Route 66 landmarks. Whether it's a commemorative ride or a relaxed stroll – today everything revolves around a century of road trip culture.

Day 7 – Tulsa – Oklahoma City
106 miles / 170 km

Today, you'll head deeper into the heart of Oklahoma and through some of the most iconic sections of Route 66. You'll pass Sapulpa, Chandler and Arcadia with the round red barn and POPS, the neon lemonade oasis with the huge bottle in front of the entrance – perfect for photos and a drink. In the afternoon, arrive in Oklahoma City with its mix of Western heritage and urban flair. Tip: Visit Bricktown or the Oklahoma City National Memorial.

Day 8 – Oklahoma City – Amarillo
260 miles / 416 km

Follow the oldest sections of Route 66 in Oklahoma, through the land of former buffalo herds, and along historic cattle drive trails such as the Chisholm Trail. Via Yukon and El Reno we go to the Route 66 Museum in Clinton. In the afternoon, cross the border into the Texas Panhandle, the southernmost part of the Great Plains. Opt to visit the Big Texan Steakhouse in Amarillo today and enjoy the legendary steaks.

Day 9 – Amarillo – Santa Fe
279 miles / 446 km

After a photo stop at the Cadillac Ranch, you will continue west, into the vast, colorful New Mexico. The landscape becomes rougher, the light softer and you feel the magic of the southwest. Santa Fe, known for its art, culture, and distinctive flair, is your destination for today.

Day 10 – Santa Fe – Free Day
0 miles / 0 km

Today the day is yours. Santa Fe, almost 400 years old, invites you to discover its markets, art galleries and the special Southwest vibe. Maybe you want to go to Taos, take a sunrise balloon ride, or take a horseback ride into the surrounding hills? Santa Fe offers you all the possibilities.

Day 11 – Santa Fe – Gallup
198 miles / 317 km

You'll head to Albuquerque, New Mexico's largest city, crossing the Rio Grande and leaving the city behind as you immerse yourself in the colors of the Navajo wilderness. Continue along mesas and rocky outcrops via Laguna and Grants until you reach Gallup – a town with a vibrant Native American culture and Route 66 flair.

Day 12 – Gallup – Flagstaff
185 miles / 298 km

After half an hour, arrive in Arizona and drive through the Petrified Forest, where ancient trees have been turned to stone. West of the national park, you'll pass Holbrook and Winslow before reaching Flagstaff, your gateway to the Grand Canyon.

Day 13 – Flagstaff – Kingman
146 miles / 234 km

Today you will experience one of the most beautiful sections of Route 66. Through Williams and the legendary Seligman, with its retro diners and photo spots, you'll travel through the desert landscapes and mountain passes of northern Arizona to Kingman – a town steeped in Route 66 history.

Day 14 – Kingman – Victorville
206 miles / 330 km

You'll drive through the Black Mountains via the Oatman Highway as wild donkeys cross your path, and continue through the Mojave Desert to California. Abandoned ghost towns and roadside spots are reminiscent of the golden days of the Mother Road. Victorville will be your last overnight stay on Route 66 before reaching the Pacific Ocean.

Day 15 – Victorville – Los Angeles
138 miles / 221 km

Today you will reach your destination: the Santa Monica Pier. Before that, enjoy the curves of the Angeles Crest Highway with fantastic views before heading down to the L.A. Basin. When you stand at the sign "End of the Trail", you experience this goosebumps moment that no one can take away from you. In the evening, you will celebrate your trip together at the Farewell Dinner.

Day 16 – Los Angeles – Departure
0 miles / 0 km

Today, your Route 66 trip ends in Los Angeles. If you would like to extend to see more of L.A. or continue to use your bike, please contact us. We are happy to help you - until the next adventure!

Ready for 100 years of Route 66?
Book your spot now and experience Route 66 as few experience it – on the bike, at your pace, with bikethebest.

Included services:

• 15 nights in 3-4 star hotels with breakfast (on travel days)
• Welcome and farewell dinner
• Transfer from the hotel to EagleRider Station and back
• Motorcycle rental (BIG TWIN) for the specified period including free miles, liability insurance
• Model Warranty
• TOP PROTECTION Additional liability insurance Euro 2 million CDW/VIP liability limitation and reimbursement of excess
• Petrol and oil (on driving days)
• Grand Canyon Helicopter Tour
• Support vehicle for luggage transport and reserve motorcycle, tools, first aid kit and drinking water
•  German-speaking tour guide on the specified dates, otherwise English or multilingual
• Original EagleRider motorcycle jacket per person
• Rental helmet for driver and passenger (subject to availability)
• one-way charges
• National park fees
• Hotel parking fees
• A major credit card is required

Services not included:

• Flight, we will be happy to provide you with a daily quote
• Personal expenses, tips, rainwear, travel insurance, etc.
• No surcharge for models with top case!