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47-110°F
8-43°C

Route 66 The Long Way Down Guided Motorcycle Tour

If riding our Route 66, Original isn’t enough, then join our Long Way Down Route 66 Harley-Davidson tour. Two extra days riding adds a fantastic diversion to Las Vegas and a visit to the Harley-Davidson® museum in Milwaukee. This journey of discovery and nostalgia is an opportunity to take the off-ramp into a bygone era and discover how America travelled in the 1920s-60s before the Interstate Highway. Experience the flair and charm of the old route. Stop at museums and historic sights, and get a great insight into the people and history of the USA. Visit wonderful old trading posts with filling stations, motels, and diners along the scenic “Mother Road”. Slow down and enjoy the scents of new mown hay and hickory smoke. Meet self-proclaimed rednecks at work and play. Travel diverse landscapes through small town America, the beautiful Rocky Mountains, the Texas panhandle, the desolate Mojave Desert, awe inspiring Grand Canyon and finish at Santa Monica Pier.

 

This is quite simply the best Route 66 guided motorcycle tour there is. We provide the personal touches no one else can, guide you to the fun places, introduce you to the characters we know, ride the hidden Route 66 sections. We follow the old route as much as possible, riding 60-70% of it, and have a number of surprises in store for you along the way to make your Route 66 experience unlike any other!

 

Total mileage c. 3000

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  • Grand Canyon

    Grand Canyon
  • Harley-Davidson® museum

    Harley-Davidson® museum
  • Chicago: Adams Street Route 66 start, Art Institute, Willis Tower, the blues!

    Chicago: Adams Street Route 66 start, Art Institute, Willis Tower, the blues!
  • Mojave Desert

    Mojave Desert
  • Las Vegas glitz and glamour

    Las Vegas glitz and glamour
  • Santa Fe, New Mexico – oldest state capital in USA

    Santa Fe, New Mexico – oldest state capital in USA
  • Petrified Forest National Park and Painted Desert

    Petrified Forest National Park and Painted Desert
  • Seligman, Kingman and Oatman historic towns

    Seligman, Kingman and Oatman historic towns
  • Santa Monica Pier- the end of the Road

    Santa Monica Pier- the end of the Road
  • Small town America

    Small town America
  • Our favourite Route 66 people, places and hangouts

    Our favourite Route 66 people, places and hangouts
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Day 1 Arrive Chicago Arrive
Day 1 Arrive Chicago

Welcome to Chicago! On arrival at O’Hare Airport, take the CTA or a taxi to our down-town hotel where you will be met by our tour guides at the hospitality desk. Afterwards you're free to go out and explore the "Windy City" of Chicago with all it has to offer. Our hotel is close to Chicago's famous blues clubs, Navy Pier, Willis Tower (formerly Sears Tower), fine dining restaurants and a vibrant nightlife. Perhaps go to the starting point of Historic Route 66 at East Adams St and South Michigan Ave. Meet your fellow riders at our Welcome Dinner this evening.

Day 2 Chicago - Milwaukee - 30 miles, 1 hr
Day 2 Chicago - Milwaukee

We pick up our motorcycles at our Woodstock dealership, have a great brunch and ride to the Harley-Davidson museum in Milwaukee, just 30 miles up the road. We are taken on an private tour of the museum, exclusive to authorized tour operators, before spending the night at the famous Iron Horse Hotel.

Day 3 Milwaukee - Springfield, IL -280 miles, 7 hrs
Day 3 Milwaukee - Springfield, IL

An early start because we've got a lot to fit in today! The ride to Chicago is uneventful, but then the fun begins as we say goodbye to Chicago and are riding down Historic Route 66 through the corn-belt of Illinois as we follow the Pontiac Trail, as Rte 66 used to be known here, to the state capital.

Day 4 Springfield - Rolla, MO - 220 miles, 6 hrs
Day 4 Springfield - Rolla, MO

Today we ride through the picturesque scenery of small town mid-America to the beautiful rolling hills of the Ozarks. The first half of the day meanders through small farming towns and countryside until we reach the border between Illinois and Missouri: the Mississippi river. We stop here to see the Chain of Rocks Bridge which became a part of original Route 66 in 1936. After lunch we stop at the Missouri Route 66 State Park, and then visit Jesse James' hideout at Meramec Caverns. Finally we arrive in Rolla for dinner and a good night's sleep.

Day 5 Rolla - Tulsa, OK - 310 miles, 9 hrs
Day 5 Rolla - Tulsa, OK

Today we weave our way from the rolling hills of the Ozarks through (another) Springfield, Joplin and Carthage until we reach Kansas. This was frontier country for much of the 19th century, and although the mountains aren’t high, the road switches, dips, and climbs providing great views of the steep hillsides of oak, elm, hickory and redbud. We stop for lunch in Kansas at the Little Brick Inn, once one of the banks robbed by the James' gang. After less than 20 miles of Kansas we move into the beautiful scenery of eastern Oklahoma.

Day 6 Tulsa - Weatherford, OK - 190 miles, 6 hrs
Day 6 Tulsa - Weatherford, OK

We head towards western Oklahoma and its wide open spaces. Oklahoma has more miles of Rte 66 than any other state, and in better condition! So it’s a real mecca for bikers and old-road fans alike. The majority of the day is spent riding the "Old 66" through pasture and prairie. We stop at the Route 66 Interpretive Center in Chandler, the Round Barn in Arcadia and ride the longest remaining stretch of the original 1926-1935 alignment of the route.
Further west we ride through El Reno, over the mile-long bridge near Bridport and end up at our hotel in the ranching and college town of Weatherford.

Day 7 - Weatherford – Amarillo, TX - 200 miles, 4 hrs
Day 7 - Weatherford – Amarillo, TX

We 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 some souvenir shopping. Then it's back on the road, passing through great plains, vast cattle ranches and small farming towns as we enter the Texas panhandle. We stop at the beautiful U-Drop Inn in Shamrock, featured in the film "Cars" as Ramone's Body shop. Then we'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?

Day 8 - Amarillo – Santa Fe, NM - 300 miles, 6.5 hrs
Day 8 - Amarillo – Santa Fe, NM

First stop, the Cadillac Ranch: a crazy farmer planted Cadillacs in his field, hoping to grow new ones – guess what?! Then it's off to Adrian, home of the Midpoint Café and our halfway point. After stopping for a coffee we leave the great plains behind and head into the natural splendour of the southwest. Riding through the wide open spaces and into the Rocky Mountains, we arrive in the beautiful city of Santa Fe where we will spend the next two nights.

Day 9 - Santa Fe Rest day
Day 9 - Santa Fe

Today is a day of rest and relaxation in one of the oldest (and highest, at over 2250 m) state capitals in the USA. Enjoy Santa Fe's numerous art galleries, specialty shops and museums, all within easy walking distance from our central hotel. Or just roam around the beautiful downtown plaza taking in its unique combination of Native American and Spanish colonial architecture. Or if you want a gentle ride, we recommend the short visit to Taos - from a biker's viewpoint probably the best day of all! Lots of bends to ride as we take the valley road there and the high country road back. Taos is famous as an artist colony and some beautiful art and Indian crafts awaiting you.

Day 10 - Santa Fe - Gallup, NM - 220 miles, 4 hrs
Day 10 - Santa Fe - Gallup, NM

It’s time to get back on the road and out into the deserts of the southwest, to our first stop for lunch in Old Town Albuquerque. Then we head on through the splendour of New Mexico’s natural beauty, ending the day in the old railroad town and Indian stronghold of Gallup and our historic hotel.

Day 11 - Gallup – Williams, AZ - 240 miles, 5 hrs
Day 11 - Gallup – Williams, AZ

Today we head into Arizona’s spectacular deserts. Our first stop is the Painted Desert & Petrified Forest National Park, where we take our time riding through the park stopping to take in its natural beauty. Afterward we stop in Holbrook to see the Wigwam Motel’s teepee shaped rooms on our way to lunch. Then it’s time to “Take it Easy” with the Eagles, standing on the corner in Winslow Arizona, before continuing to our hotel in the quaint town of Williams, gateway to the Grand Canyon.

Day 12 Williams - 120 miles, 3 hrs
Day 12 Williams

Today is Grand Canyon day. We ride the 60 miles from Williams to the canyon’s south rim, or you can take the train. Here we have time to explore on our own and see the canyon in our own time. We recommend a helicopter ride for a bird’s eye view of the vastness of the canyon. We meet up later for a sunset ride back to our hotel. This will be a day to remember!

Day 13 - Williams – Las Vegas - 300 miles, 6 hrs
Day 13 - Williams – Las Vegas

We start the day by riding to the small town of Seligman for breakfast, and give ourselves some time for shopping at its many Route 66 shops. Afterward we make our way to Hackberry and then Kingman, the self-styled ‘Capital of Route 66’, for lunch. Then comes what Americans like to call the ‘curviest’ part of the Route, the Oatman Highway, a twisting ride over the Black Mountains. We stop in Oatman to see one of the few remaining old west gold mining towns and its burros, left behind when the miners abandoned the mines. And then we head for Las Vegas, a bit of a detour, but Vegas is unique!

Day 14 - Las Vegas Free day
Day 14 - Las Vegas

The day is yours to explore this sometimes surreal city, a city full of surprises. The contrast between the ride so far and this desert metropolis is jaw-dropping. Apart from the city’s attractions, how about a ride to the Hoover Dam, the Ring of Fire or Red Rock.

Day 15 - Las Vegas – Victorville, CA - 225 miles, 4.5hrs
Day 15 - Las Vegas – Victorville, CA

We head back to Route 66 on a great route across the dramatic, desolate and always hot Mojave Desert, where once again you’ll benefit from Gary’s amazing knowledge. We stop in Amboy, located in the middle of nowhere, to check out Roy’s Motel and Café. We continue on to our late lunch stop in Barstow and then on to see Elmer’s Bottle Tree Ranch, before climbing up into the cooling pine trees of the San Gabriel Mountains. After a hot day riding through the desert our hotel’s refreshing pool beckons us to take a cool dip and relax before our last day of riding tomorrow.

Day 16 - Victorville - Los Angeles - 115 miles, 3 hrs
Day 16 - Victorville - Los Angeles

The big adventure comes to an end today with our 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 up the bike and dip your toes in the Pacific Ocean, this really is journey’s end! We take our time going to the end marker plaque, and then have a nice lunch on the pier. Afterwards you’ll have some time to look around. Then it just remains for us to return the motorcycles, and enjoy our Farewell Party.

Day 17 - Depart Los Angeles Depart
Day 17 - Depart Los Angeles

Sadly it’s time to pack our 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!

  • Our Tour Price Includes
    • Harley-Davidson® authorized rental motorcycle (current year model, dealer owned, under 20k miles with factory warranty)
    • Just 8-15 bikes per tour, never more
    • American licensed tour guide on motorcycle and assistant in support vehicle
    • Standard motorcycle insurance cover including CDW and State minimum liability cover
    • Support/luggage vehicle includes:
      • Coolbox/complimentary soft drinks
      • Spare motorcycle for emergencies
      • Trauma / First Aid kit
    • Personal hardcopy tourbook including maps
    • Fuel and oil on tour
    • Accommodation in 2-4* hotels
    • National Park, State Park and National Monument entrance fees
    • Welcome Dinner & Farewell Party
    • Some breakfasts
    • Hotel parking fees
    • Hotel to dealership transfers
    • Airport transfer in Los Angeles
    • Unlimited mileage
    • All taxes and one way fees
    • Helmets (if requested). We strongly recommend you bring your own
    • GBP pricing – we take the currency risk
    • Guaranteed financial and legal protection, for your peace of mind, from our Travel Trust Association membership and ATOL Bond
  • Pre-bookable options
    FREE ‘Try before you Fly’ Harley-Davidson® 2 hour Orientation Ride Flights (we are an ATOL bonded, UK company) Specialist Travel insurance for motorcyclists (EU residents only) Optional CDW & SLI motorcycle insurances Excursions/activities Pre and post tour accommodation and tours Pre and post tour motorcycle hire UK airport hotels and parking US Airport to hotel transfer Trike Surcharge
  • Our Tour Price Does Not Include
    • Meals except where specified (allow c. £30/person/day)
    • Riding gear
    • Additional activities
    • Personal expenses, souvenirs, tips
    • Airport to Hotel transfer (except Los Angeles)

Our Main Motorcycle Models

  • Electra Glide Ultra Limited
  • Road Glide Ultra
  • Electra Glide® Ultra Classic®
  • Road King®
  • Street Glide®/Street Glide®Special
  • Heritage Softail® Classic
  • Fat Boy®/Fat Boy® Lo
  • Dyna® Switchback ™
  • Sportster®1200 Custom
  • Tri Glide Ultra Classic
  • Bring Your Own

  • Other models may be available upon request

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