Our RideFree experience was an adventure of epic proportions. With the guidance of Wil and strategic planning, we managed to do a self-guided tour from LA to Yosemite National park,... read more through San Francisco and back down to LA in 5 days. It was a trip of a lifetime and I can't wait to hit the road again soon."
Read my full blog and story here on my website, NavigatorNick
Nick S 4/24/2020
Nathan Peach ( Overseal, Derbyshire, United Kingdom ) Just recently completed a Ride Free organised tour of Northern California, me and my buddy hatched an idea to go... read more and have an adventure in America whilst still fit and able enough to not be plagued with...More
nathanp265 11/11/2019
Wil and Erin at Ride Free organised our whole trip along route 66 then the coast road to San Francisco. A self guided driving tour we did with our friends.... read more And taking in some of the natural wonders as well like the Grand Canyon &...More
Hello Wil and Erin. Just a short note to thank you for the ‘BEST VACATION EVER’. Both Brian and Andy were exceptionally professional and it is fair to say that that trip would not have been as good without the professional and friendly banter between the group and the guides. They were well able to cater for the differences in the group and this aided the holiday. The locations, lodgings and roads traveled matched and, sometimes, exceeded our expectations. On at least two occasions the accommodations were part of our dreams. ( Log cabin on a lake ) Read More
Sturgis Rally and Colorado / Yellowstone Guided Car Tours
Explore America on the drive to the Sturgis Motorcycle Rally. Drive on an adventure through Yellowstone Park, Montana, Colorado, the Grand Canyon, Monument Valley, and Las Vegas.
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 small tight group of friends who love taking you on tour and making new friends from all over the world. The TeamCONTACT USTestimonialsPicturesMission
IT IS TIME TO BOOK YOUR STURGIS SELF DRIVE MOTORCYCLE TOUR NOW! It is best to book your Sturgis tour or any tour at least 1 year ahead.
Route 66 Guided Car Tour. Drive Historic Route 66 from Chicago to LA down the Mother Road of America. Explore old Rt 66, The Grand Canyon, Las Vegas, and more with the Oldest Motorcycle Tour Company in the USA. Fully Insured.
See the Route 66 Guided Motorcycle Tour from Chicago to Los Angeles with Las Vegas and the Grand Canyon. 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.
Pre Rt 66 Trip to Harley-Davidson Museum in Milwaukee – or – Milwaukee Start Option – add to any tours
This extra day pre trip is available as an option on all our Route 66 tours. Adds 1 or 2 days to trip.
Or Start the tour in Milwaukee, visit the Harley Museum, pick up the bikes, ride with the group to Chicago.
Harley-Davidson 115th Anniversary Celebration Museum Rally Route 66 Motorcycle Tour from Milwaukee
Part 1: We meet up for a few days of celebration at the Harley Museum in Milwaukee. Then we get our bikes and ride to Chicago.
Part 2: From Chicago we do the Route 66 Chicago to Los Angeles Harley-Davidson Motorcycle Tour
Option 1 – 15 Day 14 Night – Traditional Classic Route 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
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. This is what most motorcycle tour companies run, but we highly suggest the 16 day or 17 day tour. They turn the trip from a mission feel where you just don’t have the time you wish you had every day, into the motorcycle tour experience you were hoping for. It is not that our 16 day Rt 66 route is longer in mileage, we just give you more time to see the things you came to see, and not be exhausted like the other tours we see on the road.
Option 2 – 16 Day 15 Night – Ultra Route 66 Motorcycle Tour – or 17 day Ultimate Explorer
– can add Milwaukee Harley Museum Option
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 Rt 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
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 Rt 66 Motorcycle Tour
– can add Milwaukee Harley Museum Option
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 Rt 66 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 5B – 10 day 9 Night – We go to Santa Fe also on this trip.
Option 6 – 19 Day 18 Night – Chicago to Los Angeles Ultimate Rt 66 Motorcycle Tour
Add Harley Museum and Las Vegas Layover – starts in Chicago or Milwaukee start option
This Rt 66 motorcycle trip across America is the same as the relaxed 17 day Ultimate Chicago to LA Route 66 Harley-Davidson Motorcycle Tour, except we add in a stop at the Harley Davidson Museum in Milwaukee and a layover day in Las Vegas.
If you want to go no holds barred on your motorbike experience of a lifetime, this is the trip for you. It still also has the layover day in Santa Fe. You will have time to see so much on your trip, and with the layover days, you will be much less fatigued and tired than the 15 day trip.
We meet for orientation and dinner. We all get together and have a good time, and begin our friendships and journey together. We also pick our cars up this first day for a shakedown ride to familiarize ourselves with the car and each other.
Day 2 - Denver to Steamboat Springs – 3 hr – 153 miles
We head west into the Colorado mountains. We leave the city of Denver behind and rev our engines for the first time. An amazing ride as we head for Steam Boat Springs. Lots of beautiful scenery and some curvy mountains roads.
Day 3 – Steamboat to Green River – 5hr – 264 miles
Let’s do our best to stay off the main Highways, and see if we can find some Grizzly Bears! Ashley National Forest is our cue to head North towards Yellowstone, and the Flaming Gorge is breathtaking, and desolate. We drive our cars in to wide open remote spaces. Beautiful vistas and great roads today.
Day 4 – Green River to Jackson Hole – 3:43 hr – 200 miles
Drive our cars on tour towards and one step closer to Sturgis to the famous Jackson Hole. We are riding from the open spaces towards the larger mountains today. The road into Jackson is an amazing mountain road that follows a crystal clear stream. The long sweeping curves that we carve on our cars will keep you grinning ear to ear, and the views are breath taking. Once we arrive in Jackson, it is a really cool town to walk around and see some live music in a Cowboy bar.
Day 5 – Jackson to Cooke City, MT – 4:35 hr – 157 miles
The Grand Teton National Park and Yellowstone. What more is there? Yes, Sturgis will be great, but we are cruising Yellowstone! We might see buffalo, wolves, bears, and all kinds of wildlife. Clear mountain lakes look like a postcard. The famous Old Faithful Geyser is on our path today, and maybe a quick dip in a cool mountain stream if it is hot? Leaving Yellowstone we climb higher and deeper in the mountains. On one mountain road on the way out we have see grizzly bears in our cars. It is quite a feeling to be looking at a grizzley on the side of the road.
Day 6 – Cooke to Cody – 2:45 hr – 127 miles
The Beginning of the amazing Bear Tooth Highway to the town of Red Lodge, then Cody. As our Sturgis Motorcycle tour progresses, you will have completely forgotten about Sturgis by this time. Take time and watch the complete video above as we climb the Bear Tooth Highway. This is my favorite day of the trip. If only every day driving on tour could be like this day. For lunch the cool town of Red Lodge has some great food. Then we get into Cody and head out to see the rodeo for our evening entertainment.
Day 7 – Cody to Buffalo, Wyoming – 3:10 hr – 181 miles
Pass through the Bighorn National Forest today. Just a nice cruising day with some neat stops. The vast landscape opens again on our tour.
Day 8 – Buffalo to Sturgis – 1st Sturgis night – 2:36 hr – 183 miles or 4hr scenic )
Make some time on the road and get to Sturgis by lunch. Spend the rest of the day figuring what we are going to get into tonight! And, taking in all the sights. It is sensory overload. We also have a 4hr more scenic option, but you will be probably itching to get to Sturgis!
Day 9 – Sturgis Layover, 2nd Sturgis night – with Ride option = 30 miles or 3:10 hr – 135 miles
We start slow and give Sturgis one last shakedown before we head into the Black Hills National Forest to see Mount Rushmore and Custer State Park. Not to mention Harley Davidsons absolutely everywhere. We spend the day exploring the Black Hills and everything around the Sturgis area. Or, you can just spend the day around Stugis all day. It is up to you.
Day 10 – Sturgis Layover Day – 3rd Night in Sturgis ( or skip on 12 day tour )
An extra day to just cruise around or hang out at Sturgis, or explore surrounding areas like The Badlands. Even if you are not into the crowds, we can get out and see some amazing things today. You don’t have to spend time in crowds if you don’t want to. We will take you on great day rides. In the past we did the 2 day Sturgis, but it really takes 3 days to explore the Black Hills and take it all in.
Day 11 – Sturgis, SD to Alliance, Nebraska – 4:30 hr – 186 miles
The Badlands, Indian reservations, and The Great Plains are all part of our amazing day before we roll towards the small town USA Alliance. One last treat of America before we head into town = Carhenge!
Day 12 – Alliance to Denver – 4 hr – 265 miles
We fire up our cars for the last time and say goodbye to the Great Plains. But first we visit the Oregon Trail. This is where American settlers traveled Westward and staged before they attempted to survive a ride over the Rocky Mountians. Then we point our cars towards the town of Cheyenne, home of the American Cowboy. We give our cars a well deserved rest as we check the local saloons and take a rest ourselves. But, then saddle back up for our final leg to Denver.
We meet for orientation and dinner. We all get together and have a good time, and begin our friendships and journey together. We also pick our cars up this first day for a shakedown ride to familiarize ourselves with the car and each other.
Day 2 - Denver to Steamboat Springs – 3 hr – 153 miles
We head west into the Colorado mountains. We leave the city of Denver behind and rev our engines for the first time. An amazing ride as we head for Steam Boat Springs. Lots of beautiful scenery and some curvy mountains roads.
Day 3 – Steamboat to Green River – 5hr – 264 miles
Let’s do our best to stay off the main Highways, and see if we can find some Grizzly Bears! Ashley National Forest is our cue to head North towards Yellowstone, and the Flaming Gorge is breathtaking, and desolate. We drive our cars in to wide open remote spaces. Beautiful vistas and great roads today.
Day 4 – Green River to Jackson Hole – 3:43 hr – 200 miles
Drive our cars on tour towards and one step closer to Sturgis to the famous Jackson Hole. We are riding from the open spaces towards the larger mountains today. The road into Jackson is an amazing mountain road that follows a crystal clear stream. The long sweeping curves that we carve on our cars will keep you grinning ear to ear, and the views are breath taking. Once we arrive in Jackson, it is a really cool town to walk around and see some live music in a Cowboy bar.
Day 5 - Jackson Hole to Yellowstone
Day 6 – Yellowstone to Cooke City, MT
The Grand Teton National Park and Yellowstone. What more is there? Yes, Sturgis will be great, but we are cruising Yellowstone! We might see buffalo, wolves, bears, and all kinds of wildlife. Clear mountain lakes look like a postcard. The famous Old Faithful Geyser is on our path today, and maybe a quick dip in a cool mountain stream if it is hot? Leaving Yellowstone we climb higher and deeper in the mountains. On one mountain road on the way out we have see grizzly bears on our motorcycles. It is quite a feeling to be sitting in your car looking at a grizzley on the side of the road.
Day 7 – Cooke to Cody – 2:45 hr – 127 miles
The Beginning of the amazing Bear Tooth Highway to the town of Red Lodge, then Cody. As our Sturgis Motorcycle tour progresses, you will have completely forgotten about Sturgis by this time. Take time and watch the complete video above as we climb the Bear Tooth Highway. This is my favorite day of the trip. If only every day driving cars on tour could be like this day. For lunch the cool town of Red Lodge has some great food. Then we get into Cody and head out to see the rodeo for our evening entertainment.
Day 8 – Cody to Buffalo, Wyoming – 3:10 hr – 181 miles
Pass through the Bighorn National Forest today. Just a nice cruising day with some neat stops. The vast landscape opens again on our tour.
Day 9 – Buffalo to Sturgis – 1st Sturgis night – 2:36 hr – 183 miles or 4hr scenic )
Make some time on the road and get to Sturgis by lunch. Spend the rest of the day figuring what we are going to get into tonight! And, taking in all the sights. It is sensory overload. We also have a 4hr more scenic option, but you will be probably itching to get to Sturgis!
Day 10 – Sturgis Layover, 2nd Sturgis night – with Ride option = 30 miles or 3:10 hr – 135 miles
We start slow and give Sturgis one last shakedown before we head into the Black Hills National Forest to see Mount Rushmore and Custer State Park. Not to mention Harley Davidsons absolutely everywhere. We spend the day exploring the Black Hills and everything around the Sturgis area. Or, you can just spend the day around Stugis all day. It is up to you.
Day 11 – Sturgis Layover Day – 3rd Night in Sturgis ( or skip on 12 day tour )
An extra day to just cruise around or hang out at Sturgis, or explore surrounding areas like The Badlands. Even if you are not into the crowds, we can get out and see some amazing things today. You don’t have to spend time in crowds if you don’t want to. We will take you go great day rides. In the past we did the 2 day Sturgis, but it really takes 3 days to explore the Black Hills and take it all in.
Day 12 – Sturgis, SD to Alliance, Nebraska – 4:30 hr – 186 miles
The Badlands, Indian reservations, and The Great Plains are all part of our amazing day before we roll towards the small town USA Alliance. One last treat of America before we head into town = Carhenge!
Day 13 – Alliance to Denver – 4 hr – 265 miles
We fire up our cars for the last time and say goodbye to the Great Plains. But first we visit the Oregon Trail. This is where American settlers traveled Westward and staged before they attempted to survive a ride over the Rocky Mountians. Then we point our cars towards the town of Cheyenne, home of the American Cowboy. We give our cars a well deserved rest as we check the local saloons and take a rest ourselves. But, then saddle back up for our final leg to Denver.
Pick up cars at end of day, then welcome dinner - Viva Las Vegas! We meet up in the afternoon to go over our upcoming adventure, and then hit the town!
Day 2 – Vegas to Zion
We jump in our cars and leave the Las Vegas Strip in the dust as we head our of the desert to one of the most amazing areas of the USA. It is like a mini Grand Canyon that we get to drive through! Check out the video of riding through Zion on one of our Guided Harley Motorcycle Tours from a year past. It is like driving your car through the Land of The Lost!
Day 3 – Zion to Price, Utah
We drive North in our cars towards the open land of Utah.
Day 4 – Price to Evanston, WY
Today more open driving in our cars through as amazing mountain range on the way to the Sturgis Rally. There is so much amazing adventure before we even get to Sturgis.
Day 5 – Evanston to Jackson Hole, WY
Ride through the Teton National Forest and the famous Jackson Hole.
Day 6 - Jackson Hole to Cooke City, MT
The Beginning of the amazing Bear Tooth Highway to the town of Red Lodge, then Cody. Riding the Bear Tooth Highway is one of the highlights of the car trip to the Sturgis Rally, and one of the top highlights ever of my driving experiences. People on car tour with us describe it as like driving in the Swiss Alps, but with perfectly paved roads and perfectly banked turns.
Day 7 – Cooke City to Cody, WY
Day 8 – Cody to Buffalo, WY
Pass through the Bighorn National Forest in our cars and we have a fun night out on the town in Historic Buffalo.
Day 9 – Buffalo to Sturgis – Sturgis 1st Night.
Make some time on the road and get to Sturgis by lunch. First night in Sturgis. Spend the rest of the day figuring what we are going to get into tonight! And, taking in all the sights. It is sensory overload. Sturgis. We work our way up to Sturgis. We get to see the Sturgis Rally and experience it first hand for a day and a night, but there is so much more to see. We head west to work our way to Yellowstone National Park. Then down through the mountains, then back through Colorado to Denver. See the Sturgis madness and we will get to see and talk to all of the motorcyclist from all over the world making the Sturgis Pilgrimage. It is an amazing time because there will be so many Harley Davidsons on the road throughout the entire trip. We get to enjoy all the bikes, and great people we meet along the way. Some highlights in Colorado, South Dakota, Montana, and Wyoming are: Denver, Steamboat Springs, Sturgis Rally, The Black Hills, Mount Rushmore, Cheyenne, Yellowstone, The Bear Tooth Highway, and much more.
Day 10 – Sturgis 2nd Night – Sturgis
We start slow towards Sturgis one last shakedown before we head into the Black Hills National Forest to see Mount Rushmore and Custer State Park. Not to mention Harley Davidsons absolutely everywhere. We spend the day exploring the Black Hills and everything around the Sturgis area. Or, you can just spend the day around Stugis all day. It is up to you.
Day 11 – Sturgis 3rd Night – Sturgis
Day 12 – Sturgis to Alliance, NE
Day 13 – Alliance to Boulder/Denver, CO
We fire up our cars for the last time and say goodbye to the Great Plains, and point our cars towards the town of Cheyenne, home of the American Cowboy. We give our cars a well deserved rest as we check the local saloons and take a rest ourselves. But, then saddle back up for our final leg to Denver.
Day 14 – Boulder/Denver to Gunnison, CO
Driving the small mountain roads of the Colorado Mountains
Day 15 – Gunnison to Durango, CO
More driving in the Colorado Mountains until we get to the neat town of Durango.
Day 16 – Durango to Monument Valley
Leaving the Colorado Mountains and Rockies in our cars, we drive through the desert to the famous Monument Valley where so many Western Movies were filmed.
Day 17 – Monument Valley to Grand Canyon
An amazing drive up to the Grand Canyon. That is one big hole! Spectacular scenery and canyons on the way. We stop at a real indian trading post to buy some souvenirs before we get to the South Rim of the Grand Canyon in our cars for one of the best sunsets in the world.
Day 18 – Grand Canyon to Williams
A well deserved relaxing day. We take time to explore the Grand Canyon. Optional helicopter ride over the Grand Canyon. Then a short ride down to the neat Rt 66 town of Williams
Day 19- Williams to Vegas via Rt 66
On the last day of our car tour we ride the Route 66. The cars growls down old RT 66 stopping at some of the iconic stop along the way. Then we turn in our cars and thank them for being do good to us over this amazing car tour from Vegas, Colorado, The West, to Sturgis, and back again. Tonight we have a victory dinner!
Sturgis Tours 2021: – MORE DATES POSSIBLE FORMING – CONTACT US
(Sturgis Rally Aug 6-15, 2021 / Bonneville Speedweek is Aug 7-13, 2021)
July 27- Aug 10, 2021 – Denver to Denver – 15 Day ( 14 Day +1 with extra time in Yellowstone )
July 30- Aug15, 2021 – Chicago, Harley Museum, Sturgis, Bonneville, Vegas – 17 Day
Aug 1-15, 2021 – Chicago to Museum, Monument Valley, Grand Canyon, Vegas- option – 16 day
Our RideFree experience was an adventure of epic proportions. With the guidance of Wil and strategic planning, we managed to do a self-guided tour from LA to Yosemite National park,... read more 
