15 DAY – Route 66 Guided Motorcycle Tour

Self Drive Tours


Day 1 – Arrive in Chicago

We meet after lunchtime at the hotel and talk about our upcoming adventure on the Mother Road of America, Route 66 Chicago to LA. We also do an orientation with the bikes to familiarize ourselves with the upcoming adventure and our Harley Davidsons. Then we go out for dinner after checking out the beginning of Route 66 in downtown Chicago to discuss our big adventure!

Day 2 – Chicago to Springfield, Illinois –185 miles

Let’s hop on our Harley Davidsons and ride Route 66! We settle into our bikes, and aim for California. This is our first night on the road. See icons such as the “Gemini Giant”, “Rocket Man”, “Old Log Cabin”, the old “Marathon Oil Station”. We also stop at a Rt 66 Museum in Pontiac to learn about Route 66 and the people who make America great. That afternoon we arrive to Springfield on our Harley Davidsons and stay at a nice local hotel in historic downtown where we can have dinner at a local restaurant and celebrate our first night on the road.

Day 3 – Springfield, Illinois to Saint Louis, MO 175 miles

Riding Rt 66. Exploring St. Louis. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight? There is so much to discover and explore on the motorcycle adventure across the Mother Road of America, Route 66! Before we get to Saint Louis, we ride our Harley-Davidson motorcycles onto an old section of Route 66 that is all red bricks. Then to the historic Chain of Rocks Bridge. We will walk out on the old bridge over the mighty Mississippi River.

Day 4 – St Louis to Springfield, Missouri 216 miles

Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons. We have some great authenic BBQ for lunch, and see the World’s Largest Rocking Chair. We get to see the real America that is still here, far far away from the big cities. Then we ride down a deserted twisty old part of Route 66 on our motorcycles to Devil’s Elbow.

Day 5 – Springfield, Missouri to Oklahoma City 285 miles

A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road. Gary’s Gay Parita and the old Rt 66 Rainbow Bridge are some highlights. We visit some great old diners. This is Rt 66 on a Harley!

Day 6 – Oklahoma City to Amarillo, Texas 259 miles

The Elk Cit Rt 66 Museum is full of American history from farming to the Wild West. Welcome to the panhandle of Texas. Big Texan Steakhouse for dinner? Everything is bigger in Texas. Let’s live a little old Route 66 today on our motorcycle and tonight. You will know you are on old Rt 66 today. It will feel like a throwback to what it was like to travel Rt 66 on the road in years past. After riding your motorcycle all day you will be ready for a big steak dinner.

Day 7 – Amarillo to Santa Fe, New Mexico – 176 miles

Cadillac Ranch is a Route 66 stop we must do.  Who has ever spray painted a vintage Cadillac on Rt 66 before?  Let me ask you again in the future…   We make it to the Midpoint of Rt 66!  Then welcome to Santa Fe. Art galleries, great restaurants, great walking around…. This is really an amazing Southwest city to spend time in.  We discover the rich history and culture of Santa Fe after a big motorbike day riding Route 66 on our Harley Davidsons.

DAY 8 – Santa Fe to Gallup 191 miles

We follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel. But first let’s ride our Harleys to Maggie’s Diner, where the big fight happened in Wild Hogs! Then to Old Town Albuquerque. The historic El Rancho Hotel and Motel has hosted a numerous array of movie stars including John Wayne, Ronald Reagan, Humphrey Bogart, Spencer Tracy, Katharine Hepburn, Joan Crawford, Kirk Douglas, Doris Day, Gregory Peck, and Burt Lancaster. The rugged terrain surrounding Gallup was popular with Hollywood film makers during the 1940’s and 1950’s for the on-location shooting of Westerns. Actors and film crews would stay at the hotel during filming.

Day 9 – Gallup to Grand Canyon National Park South Rim 283 miles

First, we will stand on a corner in Winslow, Arizona. Next we ride down the main drag on Rt 66 through Flagstaff. Then, we stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said. Seeing the sun set over the Grand canyon is one of the things that everyone should see once in a lifetime. We have dinner right on the rim of the Canyon. At night, we can walk back over to the rim under the stars.

Day 10 – Grand Canyon South Rim to Williams, AZ 283 miles – Almost Full Day At Grand Canyon! – Or go for an amazing ride

What is different about Ride Free Chicago to LA Route: We stay at the top of the Grand Canyon for the sunset, unlike most tours who only stay at the bottom. We also spend a whole day at the Grand Canyon the next day, then ride to the bottom so we have more time on an amazing part of Route 66 the next day. For those that want to ride more, we have an amazing ride set up for the day. Who is up for a helicopter ride across the canyon after watching the sunrise? Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? Just relax enjoy the sites and history. Check out the Watchtower. Lots of great things to see. We get a full day in The Grand Canyon. When we are done here, we start heading back down the mountain and stop if you want for a helicopter or plane ride into the Canyon. Or maybe an old train ride? We then work our way down the hill after an amazing day to Williams for dinner and a night on the little town. Or sleep. Ready to hit the road the next am for an amazing day.

Day 11 – Williams to Laughlin, NV 190 miles

An amazing Old RT 66 day! All the RT 66 shopping you could think of. We will be on an old part of RT 66 a lot of the day. We ride our Harley motorcycles through old towns, some great shopping spots with old stores and memoralbilia. Towards the end of the day we will work our way on an incredible slow winding road to the old mining town of Oatman. Wild burros, real old 49er gold miners with real Colt 45s on their hips to protect their gold. A forgotten town. Not much has changed here the past 100 years. It is almost unbelievable that is winding mountain road was the main East West road until 1953 when Rt 66 was re routed. Time has held still since then in Oatman. Laughlin is a little Gambling town on the way to Vegas on the Colorado River. Let’s get you ready for the Big Time tomorrow. Ribeye Steak tonight!

Day 12 – Laughlin, NV to Las Vegas, NV 97 miles – Almost Full Day in Vegas!

An early morning ride out beats the heat, and gets us to Vegas early for a full day…. Plenty of time relax in your Vegas room and get cleaned up before hitting the Vegas Strip. Of course we get a picture in from of the famous Las Vegas sign when we ride in town down the strip on our Harley-Davidsons! Or, instead of just Vegas lounging, we have some great rides out from Vegas if you want some more riding. Like Red Rock Canyon and some other stops. But first the Hoover Dam! Vegas – Pools, shows, fun. We will have most of the day to explore Vegas, and the whole relaxed evening.

Day 13 – Las Vegas, NV to Big Bear Lake (or Victorville), CA 190 miles

( or we can do Big Bear Lake Option if would like) We follow the original path of Old Route 66 where we can, and explore the amazing Mojave desert. Or if you have had enough desert at this point, we will leave the hot straight desert behind and climb high above the clouds through the cool crisp mountain air on amazing twisty mountain roads to the alpine lake of Big Bear on our motorcycles.

Day 14 – Big Bear Lake (or Victorville) to Santa Monica Pier! 100 miles or add more twisties option

You think the trip is about done? No way. Some of the best motorcycling riding is today. We ride through the California mountains on our Harley or Indian motorcycles carving our way one perfect motorcycle curve after another. Before we drop down into civilization we have a great stop on top of the mountain with amazing views towards our destination. Then it is time to head over the famous Cajon Pass, then we drop into LA, freeways, civilization. We make it through all the way to the end of Route 66! The Santa Monica Pier. … let’s keep the Ride Free tradition of ending the tour by putting our feet into the cold Pacific! We turn the bikes in at the end of the day. A victory dinner tonight.

Day 15 – Los Angeles Departure

We say our goodbyes, and plan for our next adventure. There is so much more to see in the USA in the future. A shuttle will take you to the LAX.