EagleRider Route 66 Guided Motorcycle Tour

You’ll step off the plane at Chicago O’Hare International Airport and head to your hotel. Spend the afternoon settling in and exploring the city. Navy Pier, on the shore of Lake Michigan, is a popular destination with some great rides and activities. The Art Institute of Chicago is a must-see attraction, with a seriously impressive collection of paintings and art. Round off your day by meeting your guide and fellow travellers at a welcome dinner. 

Today you’ll pick up your bike and hit the open road. Your first destination is Springfield, Illinois, which is the former home of Abraham Lincoln. On the way you’ll stop for a photo with the Gemini Giant, a unique roadside attraction in Wilmington, and check out the excellent Route 66 Museum in Pontiac – the ultimate repository for Mother Road kitsch. Arriving into Springfield in the afternoon, you’ll be able to tuck into dinner and see the sights, before kicking off your boots and turning in for the night.

Rising early, you’ll have breakfast before striking out for St Louis, Missouri. You’re deep in the American heartland now. All around you are cornfields, red barns and sleepy small towns. Riding over the Chain of Rocks Bridge, you’ll cross the Mississippi River - where Mark Twain set his riverboat tales. St Louis is known as the gateway to the West and it certainly has the feel of a crossroads, with BBQ and juke joints serving up exquisite brisket and pouring cold beer late into the night.

Set your alarm for an early view of the St Louis Arch, which beautifully frames the Mississippi River. The thickly forested hills outside the city are enormous fun to ride, rising and falling gently and offering views over the land as you reach the crest. Stopping at Fanning, you’ll take in the World’s Largest Rocking Chair, which stands just over 56 feet tall. Next up you’ll ride the sharply twisting roads of Devil’s Elbow before arriving into Joplin. Among other attractions is the apartment that Bonnie and Clyde famously chose as their hideout in 1933. 

From Joplin you’ll ride for Oklahoma City, stopping to see the Blue Whale of Catoosa, a popular waterfront sculpture. As you ride, you’ll also notice several Native American reservations. This land is where many tribes were forcibly resettled during the 19th century, a sobering reminder of a relatively recent history. As you ride into Oklahoma City, you’ll pass classic diners, motels and gas stations – many of which retain their atomic age styling. The city itself is a charismatic place with a lively nightlife and some great restaurants. 

The section of Route 66 you’ll ride today was formerly a cattle trail, which ranchers used to bring cows up from Texas to the Kansas railyards. At Clinton, Oklahoma, you’ll stop at the Route 66 Museum – which features a great selection of memorabilia from throughout the highway’s history. You’ll end the day at the Big Texan Steak Ranch in Amarillo, where you can tuck into an enormous plate of prime beef.

This morning it’s time to ride through Texas, taking in the famous Cadillac Ranch and marvelling at the open plains of this huge state. At the ghost town of Glen Rio, cross the border into New Mexico. From here it’s time to begin the steady climb to the high plains and the gorgeous city of Santa Fe, where you’ll be taking a well-earned rest. 

Take your time to explore this charming city, which was founded by Spanish settlers in 1610. You can visit the nearby town of Taos Pueblo, which was built from stone and adobe mud more than 1,000 years ago and is the oldest continually inhabited settlement in all of North America. Santa Fe itself offers some great attractions, including the Georgia O’Keeffe Museum, the soaring Cathedral Basilica of St Francis of Assisi, and some excellent Mexican eateries.

Feeling fresh and well-rested you’ll begin the ride to Gallup in the morning, passing by New Mexico’s capital Albuquerque. From here you’ll cross the Rio Grande, always a magical sight, and pass on into Navajo Country. Soaring bluffs and craggy mesas emerge from the landscape - the shadows ever-changing as the sun moves through the sky. Cibola National Forest is an arresting sight, the rich greens providing welcome relief in this arid landscape. Gallup is a hardy town popular with bikers. You can look forward to swapping tall tales with fellow travellers this evening. 

Wake early for breakfast and a cup of coffee before getting back on the road. Today you’ll visit the Grand Canyon, an essential pilgrimage for visitors to the USA and one of the most extraordinary places you’ll ever see. The journey is no less spectacular. Crossing into Arizona you’ll ride through the Petrified Forest National Park, an alien landscape of fossilised trees. In Winslow you’ll stop for a photo at Standin’ on the Corner Park, immortalised by the Eagles in the hit song Take it Easy, before riding into Holbrook to spend the night in a hotel with a view over the Canyon's South Rim.

Be sure to get up early to watch the sun as it rises over the Grand Canyon. In the early afternoon you’ll pick up the trail once more, stopping en route in the quaint Route 66 towns of Hackman, Kingberry, Seligman and Oatman. You’ll spend the night at the Laughlin Hotel or similar on the banks of the Colorado River. 

Your ride today will give you your first sight of the Mojave Desert, a place of cacti, Joshua trees and cobalt-blue skies. Take a detour across the awe-inspiring Hoover Dam, one of the most remarkable engineering projects in world history, and arrive into Las Vegas in the late afternoon. In this glittering city you can pick up some chips and hit the roulette tables, or take in a show. 

From Las Vegas you’ll ride into California, the final state on your extraordinary journey. This part of the highway takes you through the beautiful Mojave and offers some of the best views of the entire route. You’ll arrive into the town of Victorville late afternoon to check into your hotel and get some dinner.

Today will be your final ride and it’s sure to be bittersweet. Between you and the Santa Monica Pier, the end of the road, stands the Angeles Crest Highway. This tricky route runs through the Angeles National Forest. You’ll descend into the Los Angeles basin and down to the pier, where the iconic ‘End of the Trail’ sign stands. Your sense of elation will be magnificent. You have just crossed almost the entire continental United States in two weeks. At your farewell dinner you’ll say goodbye to your guide and fellow riders, with whom you’ve shared this incredible experience. 

Today your trip concludes. You can take a couple of nights to recuperate by the pool in LA, or board your onward flight.