Route 66 Long Way Down

On arrival at O’Hare Airport, take the hotel shuttle to your hotel. After check in, take in the entertainment, shops and bars nearby, and maybe check out your motorcycle. If you want to discover the “Windy City” of Chicago with all it has to offer, we suggest you arrive a day early and explore at leisure:

Famous blues clubs, Navy Pier, Willis Tower (formerly Sears Tower), fine dining restaurants and a vibrant nightlife. Take a stroll to the starting point of Historic Route 66 at East Adams St and South Michigan Ave.

After breakfast, make your way to the motorcycle pick up and retrieve your ride for your Route 66 Long Way Down adventure. After getting your bike ready, ride North to the Harley-Davidson museum in Milwaukee, just 80 miles up the road. Learn all about the fascinating and varied history of the iconic American manufacturer. It’s a large, but well-designed museum, which takes you from the humble beginning of the company to today’s iconic brand.

An early start because we’ve got a lot to fit in today! The ride to Chicago is uneventful, but then the fun begins! Next thing you know you’re riding down Historic Route 66 through the cities, small towns and farmlands of Illinois. Follow the Pontiac Trail, as Route 66 used to be known here, to the state capital of Springfield.

Today you ride through the picturesque scenery of small town mid-America into the rolling hills of the Ozarks. Your morning begins by meandering through picturesque farming towns and countryside until you arrive at the Mississippi river, the border between Illinois and Missouri. Stop here for the Chain of Rocks Bridge which became a part of original Route 66 in 1936. After lunch, stop at the Missouri Route 66 State Park to learn more about the history of the route in the state. Afterward, enjoy the hills and valleys twisting through the Ozarks to Jesse James’ hideout at Meramec Caverns. Finally arrive in Rolla for dinner and a good night’s sleep, now you’re only 24 hours from Tulsa!

This morning the road twists, dips, and climbs through dense forests of oak, elm, hickory and redbud. Soon the hills, valleys and twisty roads gradually fade away as you ride through (another) Springfield, Joplin and Carthage until you reach Kansas Be sure to stop in either Galena or Baxter springs, considering there’s just under 14 miles of route 66 in Kansas. Check out the old train depot in Galena, or the route 66 welcome centre in Baxter Springs. Then you’ll ride into the gentle bends and hills of Eastern Oklahoma, and finally Tulsa. Enjoy a good night’s rest, it’s been a long but enjoyable day on your Route 66 Long Way Down tour.

Oklahoma has more miles of Route 66 than any other state, and in better condition. The majority of the day is spent riding the “Old 66” through pasture and prairie. Stop at the Route 66 Interpretive Centre in Chandler, the Round Barn in Arcadia, Seba Station Motorcycle Museum in Warwick, and ride the longest remaining stretch of the original alignments of the route. Further west you’ll ride through El Reno, over the mile-long pony truss bridge near Hydro and end up at your hotel in the ranching and college town of Weatherford.

Start today at the Route 66 museum in Clinton, where you can learn more about the route and its importance in American history, and do a bit of souvenir shopping. Then it’s back on the road, passing over the great plains, through vast cattle ranches and small farming towns as you enter the Texas panhandle. Stop at the iconic art-deco U-Drop Inn in Shamrock, featured in the film “Cars” as Ramone’s Body Shop. Then you’re off across the plains for a well-deserved steak at the Big Texas Steak Ranch in Amarillo. Are you brave enough to attempt the 72-oz (2 kg) steak dinner challenge?

First stop, the Cadillac Ranch, an ever-changing art exhibit started in 1974 by a group of eccentric artists called the “Ant farm”. Be sure to bring a can of spray paint, and let your inner hoodlum out and leave your mark on one of the cars (encouraged by the artists).  Then it’s off to Adrian, home of the Midpoint Café and your halfway point. After stopping for a coffee and the best pie on the route, you’ll leave the great plains and head into the natural splendour of the southwest. Riding through the wide open spaces of the high chaparral deserts and prairie into the Rocky Mountains. On your way keep an eye out for Pronghorn Antelope, mule deer and other wildlife. Follow the old Santa Fe cattle drive trail through Pecos National Historic Park and into beautiful Santa Fe, where you will spend the next two nights.

Today is a day of rest and relaxation in one of the oldest and the highest, (2194 m) state capitals in the USA. Explore Santa Fe’s numerous art galleries, specialty shops and museums, all within easy walking distance of our hotel. Or roam around the beautiful downtown plaza’s unique combination of Native American and Spanish colonial architecture. If you want a gentle ride, we recommend the short visit to Taos. Lots of bends to ride as you take the valley road there and the alpine forest road back. Taos is famous as an artist colony and some beautiful art and native American crafts awaiting you. Be sure to sample the local restaurants selection of New Mexican cuisine, a fusion of Mexican and Native American foods.

Time to get back on the road and out into the deserts of the southwest. Ride down into the Rio Grande valley to your first stop for lunch in Old Town Albuquerque. Then head west alongside the Navajo sandstone mesas, through the splendour of New Mexico’s natural beauty, ending the day in the old railroad town and Native American stronghold of Gallup. Be sure to stop by the historic El Rancho hotel for dinner and a look around the property.

Today on your Route 66 Long Way Down adventure you head into Arizona’s spectacular deserts. The first stop is Painted Desert & Petrified Forest National Park, take your time riding through the park, stopping to take in its natural geologic multi-coloured hues and colours. Afterwards it’s a short ride into Holbrook to see the Wigwam Motel’s tepee-shaped rooms. Then it’s time for lunch and some time to “Take it Easy” with the Eagles, and “standin’ on the corner” in Winslow, Arizona.  Finally, continuing onward to your hotel in the quaint town of Williams, last Route 66 town by-passed by interstate 40 and gateway to the Grand Canyon.

Today is Grand Canyon day! You can take the train from Williams or ride the 55 miles to the canyon’s south rim. Here you’ll have time to explore the national park’s numerous viewpoints and attractions, and be sure to go to Desert view on the Eastern edge of the park for the best views from the stone tower. We recommend a helicopter ride for a bird’s eye view and to appreciate just how massive it really is. Take a sunset ride back to your hotel. This will be a day you’ll always remember!

Start the day by taking a short ride through the town of Ash Fork, down Crookton Road into the small town of Seligman for the best breakfast on the route at Lilo’s Westside Café. Be sure to give yourself some time for shopping at its many Route 66 shops. Afterward, make your way to Hackberry and Kingman, the self-described ‘Capital of Route 66’, for lunch. Then comes what we like to call the ‘curviest’ part of the route, Sitgraves Pass via the Oatman Highway, a twisting & turning roller-coaster ride over the Black Mountains. Stop in Oatman to see one of the few remaining authentic old west gold mining towns. Bring some carrots or buy some alfalfa cubes from one of the local shops to feed the local burros, left behind when the miners abandoned their claims.   And then head for Las Vegas, be sure to stop by the Bolder (Hoover) Dam on your way there, well worth the time!

The day is yours to explore this unique and surreal city, a city full of surprises. The contrast between the Route 66 Long Way Down ride so far and this desert metropolis is jaw-dropping. There’s plenty to do, gambling of every description, shows, theatre, concerts and other amusements! It’s one giant amusement park designed for the big kids! Or if you’re looking for a short but beautiful ride, try the valley of fires and red rock state park for some amazing views.

We head back to Route 66 on a great route across the dramatic, desolate and always hot Mojave Desert. Take a break in the oasis in Fenner before making your way to Amboy, located in the middle of nowhere, to check out Roy’s Motel and Café. Continue on to a lunch stop in Barstow and then onward to see Elmer’s Bottle Tree ranch. After a hot day riding through the desert your hotel’s refreshing pool beckons you to take a cool dip and relax before your last day of riding tomorrow.

Your big adventure comes to an end today with your ride to Los Angeles. Much of the road has been lost, but the end of the Mother Road, Santa Monica Pier, is worth the wait. Park your motorcycle, have some lunch on the pier, and then dip your toes in the Pacific Ocean, this really is journey’s end! Take your time going to the end marker plaque at Ocean Avenue and Santa Monica Boulevard, and then wander through downtown Santa Monica. All that remains, the ride to the motorcycle drop-off and saying goodbye to your bike for the past two weeks. Get to your hotel and enjoy a nice celebratory dinner and drinks and some well-earned rest. You made it all the way on your Route 66 Long Way Down tour!

Time to pack your bags and head home, filled with the experiences and memories. We hope to see you back for another great tour. This is end of the road – for now!