Route 66 Tour Chicago to LA

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Ride route 66
ride route 66

This Iconic Route 66 motorcycle tour rides along America’s “Mother Road” Route 66.  Our route stretches 3,200 miles from Chicago to Los Angeles.  Crossing 3 time zones and 8 States including, Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.  On this tour we also take in Nevada.  During your tour we will take in much of Route 66’s history, original roads, restaurants, gas stations, and nostalgic landmarks that have been preserved exactly as they were in the 1950’s / 60’s.
Over the 16 days you will visit Chicago, Springfield, St Louis, Joplin, Oklahoma City, Amarillo, Santa Fe, Gallup, Holbrook, Winslow, Williams, Grand Canyon, Las Vegas, Barstow, Victorville and Santa Monica Pier. Join us on an Amazing Adventure with memories that will last a lifetime.

2018 – 1st August to 17th August

£5,995 Rider Single Occupancy
£3,895 Rider & Pillion Double Occupancy (Price p/p)

Route 66 Itinerary

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Route 66Welcome to our day of preparation for the exciting Route 66 Motorcycle Tour. This once in a lifetime journey, with it’s unique riding experience, along the most famous two-lane highway in America, could change your life for the better.

Ride Route 66Your opportunity to visit with new friends, the experience of a legendary road featured in many iconic films and television shows.

The sights and sounds of a history long forgotten by the modern age, along with the vastly diverse scenery of a landscape most have never seen, will remind us of days gone by. We are staying at the same hotel for two nights so there will be plenty of time to experience the beauty of this magnificent city.

Ride Route 66Approximate mileage: 150 miles

Today you can choose to join us for the day with a leisurely ride to the Harley-Davidson motorcycle museum in Milwaukee or take in the sights and sounds of Chicago, the choice is yours!



Ride Route 66Approximate mileage: 211 miles

This is where your riding adventure starts, all the anticipation and build up to your Route 66 tour. Leaving Chicago all refreshed after your flight we head off through the town of Joliet with a visit to the Route 66 tour Museum.

From there we ride past the Gemini Giant (pictured in this image) at the entrance to Wilmington. For those who are up to it, we will call in at another Route 66 tour Museum in Pontiac before reaching the town of Springfield for the night.



Ride Route 66Approximate mileage: 205 miles

Today we ride towards the town of St. Louis! Sticking to the 2 lane sections of the “Mother Road”.  As we arrive into St. Louis, Missouri, you will not fail to notice the magnificent Gateway Arch. This gleaming, stainless steel structure welcomes you in style.


We will also visit the Chain of Rocks Bridge, the original bridge where Route 66 crossed the Mississippi River. St Louis rests along the banks of the Mississippi River and has some of the best restaurants in the country, there is live music playing everywhere and BBQ ribs are a specialty not be missed.

Ride Route 66One of the attractions of the day is calling in to have your picture taken under a giant rocking chair that’s 46 feet tall was set up on old Route 66 four miles west of Cuba. It’s next to the Fanning U.S. 66 Outpost & General Store in the tiny settlement of Fanning. From there we ride on to Rolla for the night where there are plenty of exceptional restaurants to eat dinner.  The BBQ ribs are a specialty not to be missed.



Approximate mileage: 186 miles

Today we ride to the town of Joplin, MO.  As we leave Rolla on old Route 66 we can start to enjoy the rolling Missouri countryside that makes this area such a beautiful and exhilarating place to ride.  An early attraction for today is a ride over the “Devil’s Elbow Bridge” on the Big Piney River.
The rest of the day’s riding will weave along as much of Route 66, through Springfield before reaching Joplin for the night.


bridgeApproximate mileage: 238 miles

Today is a great days riding as we head towards the “Windy City” of Oklahoma. Our first stop is just over the state line into Kansas to ride over the Marsh Arch Bridge.  The riding is easy going as we head for lunch.


blue whaleFollowing lunch we visit the famous Blue Whale which has become one of the most recognizable attractions on old Route 66 in Oklahoma.  The Blue Whale and its pond became a favourite stop and swimming hole for both locals and travelers alike.



route 66Approximate mileage: 310 miles

Today’s ride goes up a notch in terms of mileage.  After breakfast we start riding towards Clinton to visit the Route 66 museum. This is a great place to purchase those all-important “Route 66” gifts. Feeling inspired by the memorabilia within the museum we mount our trusty steeds and ride off America’s mother road Route 66.  A light lunch is the order of the day.

Big TexanIf anyone feeling up for a challenge, today’s the day! You will be eating dinner at the world famous Big Texan steakhouse in Amarillo famous for the 72oz challenge. To date Blue Cucumber Tours has not had anyone brave enough to take the ultimate challenge, could you be the first?



Approximate mileage: 282 miles








route 66If you were wondering why there was “a can of spray paint” on your kit list, this is the reason!  Our first stop is to the Cadillac Ranch a short ride from the hotel. When you have finished being a graffiti artist we ride off into the distance on Route 66 to the historic city of Santa Fe for dinner and a much needed rest.




Approximate mileage: 211 miles

route 66The Roadrunner State beckons adventurers with atmospheric small towns that radiate authenticity. Gallup is easy to get to and easy to love. A slice of Americana rarely seen nowadays, it has barely changed since Route 66’s mid-century heyday. The drive from Santa Fe to Gallup whisks you across spectacularly scenic Route 66, now prosaically known as I-40.

Where mile-long Santa Fe Railroad freight trains chug alongside 66 in the shadow of towering orange mesas, where magic hour seems to stretch forever, erupting in blazing vermilion sunsets.
You’ll know when you’re in Gallup; its vintage neon signs twinkle like tinsel strung on Route 66.
Once a railroad hub, Gallup is now the commercial capital of the vast, 300,000-strong Navajo Nation homelands that surround it.

route 66Approximate mileage: 287 miles
We have a surprise in store for you as the group heads north for a ride through the Salt River Canyon where you will be astounded by it’s natural beauty.  In the afternoon you will experience a number of iconic Route 66 sights and landmarks as we take time to enjoy the beauty of the landscape.  We then head off to “the wigwam motel” for an evening with a difference.

route 66Approximate mileage: 352miles
An early start takes us to the town of Winslow for a great photo opportunity and chance to pick up some Route 66 souvenirs. This is followed by a ride out to visit the Meteor Crater.  From there we head off to Flagstaff for a light lunch.  After lunch we enjoy a ride down through Oak Creek Canyon, Sedona and Jerome National Park, we then ride north again to visit the Grand Canyon before ending the days ride at one of the most iconic Route 66 towns called Williams for an evening of entertainment and food.
route 66Approximate mileage: 286 miles
This morning we head west to the historic ghost town of Seligman where we will ride along old Route 66 for an early lunch at a classic old Route 66 Diner in Kingman.  After lunch, we take in the amazing town of Oatman before landing in Las Vegas for the afternoon and evening of fun.


route 66Approximate mileage: 98 miles
Today is designed as a rest day for you to enjoy the sights and sounds of the Las Vegas Strip (Remember, what happens in Vegas stays in Vegas!).  There will be optional rides and activities available including the Hoover Dam and  Lake Mead.


route 66Approximate mileage: 234 miles
After a lazy start, we leave Las Vegas and head south through Searchlight for an interesting outer-space encounter in the town of Baker. We then ride into Barstow and stay on Route 66 for the rest of the day where the scenery and roads will take you back to time gone by.

route 66Continuing South West we leave Nevada and ride into California for a stop at the Bottle Tree Ranch and California Route 66.

route 66There is a wide range of typical Route 66 memorabilia for you to purchase.




route 66Approximate mileage: 220 miles
As we head off for the “end of the trail” sign on the Santa Monica Pier on our final days riding along America’s Mother Road Route 66, we snake our way over the Angeles Mountains for 67 miles of riding heaven. There will be an opportunity relax, eat and enjoy the sunshine before heading to the hotel to park the bikes for the last time.
end of the trailIn the evening there will be plenty of time to relax before we sit down for a celebration meal together whilst reflecting on the weeks achievements.




Enjoy the morning in Los Angeles before your flight home to the UK
♦ 15 nights of quality hotels / motels.
♦ Welcome Dinner and Tour Briefing.
♦ Daily breakfast.
♦ Guaranteed choice of rented motorcycle.
♦ Unlimited mileage.
♦ All fuel and oil for your motorcycle.
♦ Optional visit to the Milwaukee Harley Davidson Museum & evening in Chicago.
♦ Admission fees to all Museums and National Parks (on our scheduled route).
♦ Any tolls, parking fees (any gratuities are additional).
♦ The tour will be guided by a professional Route 66 veteran who will give daily summaries and tell of the history of Route 66.
♦ Transfers to and from the Airport and Hotel.
♦ Motorcycle rental and the required liability insurance.
♦ 24 hour roadside assistance.
♦ Support vehicle at all times with a spare bike.
♦ Luggage carried on the support vehicle.
♦ Ice cold water, soft drinks and snacks throughout each day.
♦ Farewell celebratory get together and meal.
• Your airfare to and from the US.
• Your ESTA (Visa Waiver to travel to the US) This costs $14 from the US Embassy / website
• Personal Travel Insurance.
• Additional meals and snacks, tips, refreshments other than those specified.
• Alcoholic Beverages.
• Trip Cancellation Insurance or Personal Travel Insurance.
• Personal Souvenirs.
• Shipping of any excess baggage, souvenirs, helmets, etc … To or from to your home.
• Any necessary riding gear and / or personal effects.
• Any additional or supplemental insurance for personal effects or public liability.
• Anything not mentioned in the list of included items above.
Contact us on: 03333 660742 or use the contact form below


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Average rating:  
 4 reviews
Great Advice!

We met Darren while travelling Route 66 as a couple. We had hired our bikes through EagleRider which in hindsight was more difficult than we had imagined. Navigating the old Route 66 by ourselves was much more challenging than we had thought, and we were often lost or hit dead ends on the way.We also had a mix up in our accomodation from EagleRider (was booked for a Springfield in a different state) and some of the accomodation was average to say the least.We met Darren in Sante Fe and he invited us to dinner with his touring group. He (and the rest of his group) were all super friendly. Darren was great and provided us with fantastic route instructions and places to see through to LA. We ended up seeing amazing sights that we hadn't originally planned and would have missed if we hadn't run into Darren.

Trip of a lifetime!

Such a wonderful trip, did exactly what it says on the box. Great company, friendly tour guides, nothing was ever too much trouble. Personally I haven't been on tours with others before, so having a relatively small group allowed it to remain very personal. Hotels were of a great standard, and I certainly gained a few pounds!! I look forward to completing another tour with BC Motorcycle Tours next year.

A wonderful experience

In 2016 I was able to undertake a number of motorcycle tours in the US, this one was for me the very best. To travel across America along Route 66 was a great feeling, to see the sights and to take in the hospitality of local residents as we passed though on our journey of discovery. One of the things I liked most about this tour was that it was a fairly small group unlike some of the other tour groups we met along the way. I was able to get to know everyone and shared many a great laugh as we passed along this iconic highway.

by Scott Moore on Route 66 Tour Chicago to LA
Chicago to LA

In August 2016 I embarked on a what I thought was a one off road trip on in my wildest dreams from start to finish I was buzzing the sights I saw was out of my dreams finally riding the road which songs and movies are made about as they say get your kicks on Route66 that is so true some amazing sights along the way the people are so friendly and welcoming. How to put into one word AMAZING you just have to do at the end of the tour I didn't want it to finish I had tears in my eyes I just wanted to turn round and do it all over again next month I am doing it again and I can't wait 😎😎😎