Route 66 Motorcycle Tour




Route 66 Motorcycle Tour.  Ride Historic Route 66 from Chicago to LA on a guided motorcycle tour USA  down the Mother Road of America on a Harley Davidson motorcycle.    Explore old Rt 66, The Grand Canyon, Las Vegas, and more with the Oldest Motorcycle Tour Company in the USA.  Fully Insured.

Click Here for PICTURES and VIDEOS  These will show what Ride Free  is truly all about.
Click Here for Pictures from Route 66 Guided Motorcycle Tour Aug 2014   , 2013 Trip
Click Here   For 850 Pictures of the entire Route 66 Motorcycle Tour 

route 66 motorcycle tour on Harley Roys Diner

See the Route 66 Chicago to Las Vegas with Grand Canyon 15 Day Option.  Or for a shorter Route 66 trip, you can join on a motorcycle the portion from Albuquerque to LA on Route 66.  This is a 10 Day Tour.

What is different about Ride Free Chicago to LA Route:  We typically run smaller more personalized tours than other Chicago to LA Motorcycle Tour Companies. We stay at the top of the Grand Canyon for the sunset and sunrise, unlike most tours who only stay only at the bottom.  We also spend a whole day at the Grand Canyon the next day giving time for a helicopter ride or donkey ride, then ride to the bottom so we have more time on an amazing part of Route 66 the next day.  We also get to Vegas early so you have a full afternoon and relaxed evening in Las Vegas.

RT 66 Chicago to LA  All Inclusive
$595 return fee included at no extra charge to you (Chicago starts only),  Breakfast, Gas, Tour Guides, Support Vehicle, National Park Fees, Motorcycle, Lodging.    Not included: Optional Helicopter ride at the Grand Canyon, insurance options, lunch and dinners, tour guide gratuity.

Self Guided / Drive Motorcycle, Route, Lodging, Support

Pre Trip to Harley-Davidson Museum and Factory Tour in Milwaukee
This pre trip is available as an option on our Route 66 tours.   We take a couple days and see where Harley’s are born!

Option 1 – 15 Day 14 Night – Traditional  Classic Route 66 Motorcycle Tour
This is the Traditional Route 66  Chicago to LA Harley-Davidson Motorcycle Tour.  Ride Free includes almost a full day at The Grand Canyon on this motorbike trip across America, or explore the area on your bike that day.  And, we arrive early to Las Vegas so you have a full afternoon and night in Las Vegas, or we can ride the Red Rock Canyon by Vegas or The Valley of fire. Optional helicopter ride at Grand Canyon.

Option 2 – 16 Day 15 Night – Ultra Route 66 Motorcycle Tour – or 17 day Ultimate Explorer
This is the traditional Route 66 Chicago to Los Angeles Motorcycle Tour, BUT with a couple of extras.
We explore Rt 66 where most tours ride right by, and we add days so we have time to explore more without days being too long on our motorcycles.  # Wil highly recommends this over any 15 day Rt 66 Route.
We add a day in the middle of the trip = shortens the riding days.  Our 15 day is the industry standard, but there are some very long riding day, if you add a riding, it will make the 3 long days into 4 nice days.   Well worth it.  Or add 2 extra riding days for a 17 day Route 66 Motorcycle Tour, and is even more relaxing.   This is how Wil would choose to do it every time.  You are only doing this once, believe me now or later…
## Note:  don’t let the mileage fool you, much of our trip exploring  is slow moving and takes a long time.  And, you don’t want to miss all the history and attractions.

Option 3 – 13 Day 12 Night – Chicago to Las Vegas Motorcycle Tour
This motorcycle trip across America is the same as the Traditional Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Chicago to Las Vegas on Route 66.   

Option 4 – 10 Day 9 Night – Chicago to Albuquerque Motorcycle Tour
This motorcycle trip across America is the same as the Ultra  Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Chicago to Santa Fe / Albuquerque on Route 66.

Option 5 – 9 Day 8 Night – Albuquerque to Los Angeles Motorcycle Tour
This motorcycle trip across America is the same as the Ultra Chicago to LA Route 66 Harley-Davidson
motorcycle tour, but we ride our motorbikes Albuquerque / Santa Fe  to Los Angeles on Route 66.


OPTION 1:  15 DAY 14 NIGHT – Traditional Classic Route 66 Motorcycle Tour

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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!


 

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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.


 

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Day 3 – Springfield, Illinois to Saint Loius, MO 175miles
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.


 

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Day 4St 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. 


 

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Day 5Springfield, 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!


 

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Day 6Oklahoma 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.


 

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Day 7
Amarillo to Santa Fe, New Mexico – 279 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.


 

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DAY 8Santa Fe  to Gallup – 191 miles plus excursions
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.


 

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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.


 

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Day 10Grand Canyon South Rim to Williams, AZ – 51 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.


 

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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 12Laughlin, 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 Victorville, CA – 190 miles
( or we can do Big Bear Lake Option if want, see Ultra Tour below )
We follow the original path of Old Route 66 where we can, and explore the amazing Mojave desert. 


 


 

Day 14 Victorville  / Big Bear to Santa Monica Pier! – 100 miles.
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 15Los 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.

We highly suggest our 16 Day Rt 66 Option, itinerary below.  The days are long with so much to see, the 15 day is much more grueling than you would expect.  Do the 16 day and we divide the longest 15 tour day in half.  So much better, it is unbelievable till you do it.   Trust me.  Believe me now or later…

Guided Tour – Per Person                       10 Day 9 Night                    13 Day 12 Night        15 D 14 Night                 16D 15N Ultra 17D 16N Ultimate
2 People – 1 Bike – 1 Room $3340 + $213$4119 + $298 $4499 $4912 $5525
2 People – 2 Bikes – 1 Room $4200 + $425$5238 + $595 $6990 $7390 $7995
1 Person – 1 Bike – 1 Room $4988 + $425$6452 $7699 $7999 $8595
Self Drive Tour Per Person10 Day 9 Night13 Day 12 Night15 Day 14 Night16 Day 15 Night Ultra17D 16N Ultimate
Self Drive 2 Riders 1 Room$2311 + $425$3145 + $595$3700 + $595$3978 + $595 one way fee $4256 + $595 one way fee
Self Drive 1 Rider 1 Room$3100 + $425$4201 + $595$4925 + $595$5291 + $595 one way fee $5657 + $595 one way
 We are the OLDEST MOTORCYCLE TOUR COMPANY IN THE USA, since 1993. We are not the largest, fanciest, or most corporate tour company; we are a tight group of friends who love taking you on tour and making new friends from all over the world.  Fully Insured Tour Company.
The Team  CONTACT US  Testimonials  Pictures  Mission
Contact Us  FOR MORE DATES CONSTANTLY FORMING
Chicago to LA Motorcycle Tour – Start Dates
2016: May 5, 12, 19  –  June 9, 23  –  July 7, 21  –  Aug 4, 18  –  Sept 1, 8, 15, 22, 29  –  Oct 2, 13
2017: May 5, 12, 19  –  June 9, 29  –  July 6, 20  –  Aug 3, 17, 31  –  Sept 7, 14, 21  –  Oct 2, 12

Tour Schedule with More Dates

ROUTE 66 ULTRA MOTORCYCLE TOUR ITINERARY 16 DAY 15 NIGHT


Day 1 Arrive in Chicago
We meet after lunchtime at the hotel. We also do an orientation with the bikes.
Then we go out for dinner to discuss our big adventure!

Day 2 – Chicago to Springfield, Illinois- 185 miles
Start Tour out of Chicago. Let’s go! 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 the RT 66 Museum in Joliet.

Day 3 – Springfield, Illinois to Saint Louis- 175 miles
Today we ride over the famous old red brick section of Rt 66.  It is a tucked away little gem.  Amazing day riding Rt 66. Exploring St. Louis. Then we ride our bikes to the famous Rt 66 Chain of Rocks Bridge that goes  over the mighty Mississippi River. The Gateway Arch welcomes travelers heading East or West. The famous Budweiser Brewery. Maybe a blues bar tonight?

Day 4 –  St Louis to Lebanon, MO – 153 miles
Riding our motorcycles on Rt 66 through neat little towns, we have really fallen into synch with our Harley Davidsons.  Americana. Devils Elbow is amazing.

Day 5 – Lebanon to Tulsa, OK – 233 miles
A great section of RT 66 with all the Googie Architecture. A really great motorcycle ride on old pavement of the Mother Road.  We visit some great old diners.
This is RT 66!

Day 6 – Tulsa to Clinton OK – 191 miles
Elk Cit Rt 66 Museum. Welcome to Texas! The panhandle of Texas. Big Texan Steakhouse for dinner?

Day 7 – Clinton to Amarillo, TX – 176 miles
Welcome to Texas! 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.

DAY 8 – Amarillo  to Santa Fe, NM – 279 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…   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 day riding Route 66 on our Harley Davidson.

Day 9 – Santa Fe to Gallup – 199 miles  ( add a layover hear for the 17 day Ultra Explorer )
We start the day riding the curvy hills to Maggie’s Diner where the big showdown was in “Wild Hogs”.  Then lunch in Old Town Albuquerque. Next we follow the Route 66 path, and end at the little town of Gallup, at the Rancho Hotel.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 10 Gallup to Grand Canyon National Park – 283 miles
We stay on top of the Canyon and watch the sunset the first night. The Grand Canyon. “That’s one big hole!”, enough said.

Day 11 Grand Canyon to Williams, AZ – 51 miles
Hike down a trail the next am. into the Grand Canyon. Ride the donkeys down the trail into the canyon? 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 Western town. Or sleep. 

Day 12Williams to Laughlin, NV – 190 miles
The quintessential Western Old RT 66 day! All the RT 66 shopping you could think of. We will be on the forgotten RT 66 a lot of the day. Grand Canyon Caverns, Peach Springs, Kingman…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 and Mico Brewery tonight!

Day 13 Laughlin, NV to Las Vegas, NV – 97 miles
An early morning ride out beats the heat, and gets us to Vegas for an early lunch….. But first the Hoover Dam!
Vegas – Pools, shows, fun. We will have a lot of the day to explore Vegas, and the whole evening.

Day 14Las Vegas, NV to Big Bear Lake, CA – 224 miles or Victorville
We take a little Rt 66 excursion up into the amazing San Bernadino mountains. A last long hard ride through the desert, we are covered in desert dust. Our bikes are covered in road grime. They and we look and feel like we really did something. We have. Then a climb up into the twisty mountains brings us to an awaiting pool in the cool alpine town of Big Bear Lake.

Day 15 Big Bear Lake to Santa Monica Pier! – 113 miles
It is not over yet! We ride the Rim of The World. An incredible ride on the top of a mountain range, with the clouds below. One of our most amazing rides.  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 16 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.

route 66 harley motorcycle tour