2 extra days riding, new stops en route, 5 new stopover cities & centenary celebrations!
Tours running in May, June & September 2026
Route 66 Centennial
QUITE SIMPLY, THE MOST FAMOUS ROAD TRIP IN THE WORLD. If you are only ever going to do one iconic motorcycle ride in your life, then Route 66 is it! The Mother Road, the original motorised migration route West, was created in 1926. To celebrate its 100th year, we are running three exclusive Route 66 Centennial tours in 2026. These tours are two days longer than our original tour, and include exciting new features: the Harley-Davidson Museum and Milwaukee Bike Nite, the St Louis Arch, Petrified Forest any many new historic stops and hotels. In addition to all that, you’ll be taking part in the celebrations along the route, all with our acknowledged Route 66 expert Gary Fleshman as your guide. Travel in the tracks of those great pioneers and immerse yourself in automotive history. From Chicago, farmlands fade to great plains, rolling hills rise into scenic mountain ranges, canyons and deserts turn into valleys and eventually the route reaches the stunning Pacific Coast. Route 66 is about so much more than the riding – the people of Route 66 are what makes the Mother Road truly legendary, and we’ll make sure you meet some of the Route 66 legends.
Highlights
— Harley-Davidson Museum tour & bike night
— Chicago: Adams Street Route 66 start, Art Institute, Willis Tower, the blues!
— St. Louis Arch
— Santa Fe, New Mexico – oldest state capital in USA
— Petrified Forest National Park and Painted Desert
— Grand Canyon
— Meteor Crater
— Crossing the Mississippi River
— Seligman, Kingman & Oatman: historic towns and twisty roads
— Santa Monica Pier- the end of the Road
— Los Angeles
Itinerary
Day 1
Arrive Chicago
Welcome to Chicago! On arrival, take the airport shuttle to our hotel. Once at the hotel you can either relax, visit downtown Chicago, for numerous sightseeing, dining and shopping opportunities (our hotel is just two blocks from the Rosemont Blue Line CTA station), or visit the nearby entertainment / shopping complex. Just be back in time to meet your tour guides at the hospitality desk, get signed in and enjoy the complimentary welcome dinner this evening.
Day 2
Chicago – Milwaukee, WI
(90 miles)
Today we will make our way north to Milwaukee, Wisconsin to visit the Harley-Davidson Museum. To get there, we will take the Old Skokie Highway, a road that pre-dates the interstate. There you will have plenty of time to go through the museum at a leisurely pace, be able to see and experience all there is in the museum and, shop for exclusive museum merchandise at the on-site shop. We will have lunch there at the Motor Bar & Restaurant. After checking in at the hotel and dinner downtown, we head back to the museum for Bike Night where music and motorcycles merge for a fun-filled evening.
Day 3
Milwaukee – Bloomington-Normal, IL
(240 miles)
We start our journey across the United States on one of the most well-known roads in the world today! We leave Milwaukee and ride back to Chicago where, downtown, we will start the route with a brief photo stop at the “begin Route 66” sign at E. Adams St. and Michigan Ave. And then our journey on the infamous Historic Route 66 begins! Along the way today we’ll stop for lunch and then visit a restored mid-1930’s Texaco gas station across the street, allowing for lunch to settle before getting back on the bikes. Later we will stop at the Route 66 Association Museum of Illinois in the little town of Pontiac before landing at the hotel for this evening.
Day 4
Bloomington-Normal, IL – St. Louis, MO
(180 miles)
The majority of the day today you’ll be in the countryside and farmlands of southern Illinois. Our first stop will be in the very small town of Atlanta (not Georgia), for the recently opened American Giants Museum. Here we’ll see the largest and best collection of “Gemini Giants”, huge fiberglass statues in various forms, which used to be all along the route. Here you can learn about how these statues were made, modified and displayed to draw in customers, and their eventual decline as the interstate bypassed Route 66. After lunch at the Cozy Dog Drive In Restaurant, a Route 66 iconic stop, owned and operated by the Waldmire family, since 1946 we will ride in the direction of Springfield, the capital of Illinois. The next stop is for tea in the picturesque county seat town of Carlinville where Abraham Lincoln first set up a small log cabin and began his law practice for the locals. We will resume our journey on the old road, gradually making our way toward St.Louis, Missouri. En route, our last stop is a surprise and Orange & Black tour exclusive, one which we’re sure you won’t forget! Then it’s over the mighty Mississippi river and into the state of Missouri and into the city of Saint Louis. Just a few blocks away from the Gateway Arch Monument, visit this architectural wonder and symbol of the westward expansion of the United States!


Day 5
St. Louis – Springfield, MO
(225 miles)
Winding our way through the Ozark mountains today, twisty roads and rolling hills and valleys await us. Our first stop is at the Missouri Route 66 State Park and Museum. From there our route takes us to Meramec Caverns, once the hideout for the folk-heroes and outlaw bandit brothers, Frank and Jesse James where we’ll have some time to look around. We’ll stop for lunch at the Missouri Hick Bar-B-Q, in Cub, MO for some slow-smoked delicious meats. Located next to the historic and well-known Wagon Wheel Motel, opened in 1934 and one of the oldest, continually operating motels along the route, after lunch we’ll take some time to check out this landmark. Back on the bikes, we’ll ride through the small town of Cuba, with its famous murals, several of which depict Cuba’s history of Route 66 and then on to “Devil’s Elbow” and the bridge over the Meramec River. From there we will continue to riding, the Ozark hills slowly disappearing, the great plains opening up as we progress. We end our day in the town of Springfield, the hometown and HQ of Bass Pro Shops. Here you will find ANYTHING related to outdoor recreation – boating, camping, hunting and especially fishing. Our hotel is only a short distance from their massive flagship store where you can shop or just visit. Here they have their own giant salt and freshwater aquariums, swamp, and indoor waterfalls and taxidermy exhibits.
Day 6
Springfield – Tulsa, OK
(190 miles)
Into the vast openness of the great plains we go! The first part of the route today is a long straight stretch of almost 90 miles! We’re headed to Kansas, the third state on our tour, and the one with the least miles of Route 66 in any of the 8 on the route, through to Oklahoma, the state with the most miles of Route 66! Crossing into the state, we’re in the county where the Joad family , featured in John Steinbeck’s novel “The Grapes of Wrath” began their journey to California. We retrace their path through the rest of Oklahoma, Texas, New Mexico, Arizona and California, on the same road they took on their migration of desperation during the great dust bowl of the early 1930’s. We will stop at the Totem Pole Park, just outside of Foyil, OK. The World’s Largest Concrete Totem Pole located in this unique sculpture park is impressive! After riding some more, our final stop for the day is the Blue Whale of Catoosa, a beloved historic landmark along Route 66. From there it’s a short ride – 20 miles(ish) – to our hotel in the oil city, Tulsa.
Day 7
Tulsa – Weatherford, OK
(180 miles)
We head towards western Oklahoma and its wide-open spaces this morning. Oklahoma has more miles of Route 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 pastures 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 1928 -1935 alignment of the route.
Further west we ride through El Reno, over the mile-long pony-truss bridge near Hydro and end up at our hotel in the ranching and college town of Weatherford.
Day 8
Weatherford – Amarillo, TX
(190 miles)
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 tonight?


Day 9
Amarillo – Santa Fe, NM
(305 miles)
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 10
Santa Fe
(free day)
Time for some 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, speciality shops and museums, all within easy walking distance of our hotel. 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 Native American crafts awaiting you.
Day 11
Santa Fe – Gallup, NM
(210 miles)
It’s time to get back on the road and out into the deserts of the southwest, to our first stop for lunch in Albuquerque Old Town. Then we head on through the splendour of New Mexico’s natural beauty, ending the day in the old railroad town and Native American stronghold of Gallup and our historic El Rancho hotel.


Day 12
Gallup – Flagstaff, AZ
(185 miles)
We start this morning over a mile above sea level and ride on the interstate to our first stop. It may be a bit chilly to start but it should soon warm up. At the Petrified Forest & Painted Desert National Park you can observe a unique and stunning landscape, comprised of layers upon layers of colorful volcanic ash, separated and capped by layers of ancient sandstone. We’ll take time in the park to look around and ride the 28 miles through this amazing landscape, before making our way to our next stop. Now riding through wide-open landscape, with only sagebrush and high chaparral grasses and cactus to Holbrook, we will do a brief picture stop at the Route 66 icon, the Wigwam Motel. We stop for lunch at the El Falcone Restaurant in Winslow, Arizona. Afterwards, downtown, you’ll have the opportunity to be “Standin’ on a corner in Winslow Arizona”……….remember the Eagles song “Take it easy”?
From Winslow, we ride on to our next “out-of-this-world” destination, Meteor Crater Arizona! And then, we continue, riding westward to Flagstaff, AZ where we will spend the night. We are nearby and tomorrow we visit the Grand Canyon!
Day 13
Flagstaff – Williams (via Grand Canyon)
(175 miles)
Today we will visit the Grand Canyon, one of the 7 wonders of the world! We’ll head North, on our way stopping for food for a picnic lunch and entering the National Park at the East entrance where there is just over a mile to get to the best viewpoint of the canyon. From Desert View and the “Watchtower”, you’ll get an opportunity to ride on your own along the one road that goes along the edge of the canyon. You can stop at any of the various viewpoints along the way for more sightseeing, and to find a great place to enjoy your picnic lunch. We’ll rendezvous in a few hours at a spot in the small town just outside of the southern park entrance. It’s just over 27 miles to our rendezvous point, where we’ll meet before moving on.
From here we get on the bikes and head South to the town of Williams. You’ll have time here for dinner and to explore. We should get into town and to our hotel in enough time to get cleaned up, go get some dinner and explore the town a bit. Enjoy a stroll along the historic main street where antique street lamps decorate the sidewalks. Historic Route 66, which runs through Williams, was in former times the “Main Street of America”. It was only in 1984 that Interstate 40 was built, leading traffic around the town.
Day 14
Williams – Needles, CA
(195 miles)
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. Then we’re off to Hackberry and then Kingman, the self-styled ‘Capital of Route 66’. Next 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 reach the Colorado River, California and Needles, our next historic Route 66 town.


Day 15
Needles – Victorville, CA
(200 miles)
We start the day by riding over the Spirit Mountains into the dramatic, desolate and hot Mojave Desert, stopping in Amboy, located in the middle of nowhere, to check out iconic Roy’s Motel and Café. We continue to our lunch stop in Barstow and then on to Elmer’s Bottle Tree Ranch. After a hot day riding through the desert our hotel’s refreshing pool beckons us to take a cool dip and relax.
Day 16
Victorville – Los Angeles
(120 miles)
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 in the afternoon and enjoy our Farewell Party this evening.
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!
Total Distance c. 2700 miles
Dates & Prices
Prices are per person. Secure your booking with just a £500 deposit!
Date Rider +1, sharing 2 Riders, sharing Solo 06 - 22 May 2026 £5,645 £6,895 £8,875 03 - 19 Jun 2026 £5,645 £6,895 £8,875 02 - 18 Sep 2026 £5,645 £6,895 £8,875 A £250 discount per person will be applied if you have ridden Route 66 before on a guided tour from ANY recognised tour operator.
A 5% discount applies to bookings of 4 or more riders.
A 5% discount applies for members of the MAG, the Harley Owners Group and Curvy Riders.
A £50 credit will be applied to bookings made by O&B customers that have toured with us before.
NOTE: Discount applies to tour price only and only one (the best) discount per booking applies.
ALL BOOKINGS are eligible for a 10% discount off purchases online or instore at Infinity Motorcycles.
Bike Band A Bike Band B Bike Band C Harley Street Glide Grand Touring Electra Glide Ultra HarleyTriGlide trike Harley Road Glide Harley Street Glide Harley Road King Harley Heritage Softail Harley Low Rider Harley 1200 Sportster Motorcycle surcharges:
Band A add £zero per bike
Band B add £267 per bike
Band C £2720 per trikeYour Route 66 Centennial tour price includes:
H-D Museum Tour
Milwaukee Bike Nite
Chain of Rocks Bridge Crossing
Gateway Arch National Park
Route 66 Interpretive Centre
Route 66 Museum, Clinton
Petrified Forest/Painted Desert National Park
Meteor Crater Natural Landmark
Grand Canyon National Park pass
Welcome and farewell dinners
Limitless water, ice and fruit in the support van
FuelWorth £400 per person!
Optional pre-bookable Grand Canyon 45-minute helicopter ride: £360/per person
‘Breathtaking’, ‘an absolute must do’ and ‘definitely worth the money’ say our customers who have experienced this optional, but exceptional, 45-50 minute flight. Your Canyon Spirit tour departs from the South Rim of the Grand Canyon taking you over the beautiful Kaibab National Forest, home to the world’s largest ponderosa pine forest. Upon reaching the edge of the canyon, the South Rim gently drops away. The North Rim and eastern end of the canyon come into view. This is one of the most spectacular views in the entire canyon!
Other pre-bookable extras:
Pre-bookable extras Basis Price VIP-Zero ($0 excess CDW) Per bike £630 SLI Per bike £450 Model guarantee Per bike £93 US arrival airport-hotel transfer Per person Included US arrival hotel pre-tour Per room per night £225 US departure hotel post-tour Per room per night £182 US departure hotel-airport transfer Per person Included What's Included & What's Not
Price Includes Price Excludes 16 days Harley-Davidson® motorcycle rental
Welcome and Farewell dinners, some breakfasts
Fully equipped support van
Deputy guide who can also ride
Spare motorcycle
Fuel
All taxes,compulsory charges and one-way fees
National Park and other entrance fees
Conference, rally and other event surcharges
Parking fees
Detailed personal tourbook and tour souvenirs
Orange & Black Travel Guide to the USA and Canada
Orange & Black £ price guarantee, no exchange rate worries
ATOL protection (when we book your flights)
Peace of mind from our Travel Trust Association membership
Motorcycle Security Deposit
Optional extras/activities
Meals except where specified (allow c. £40-50/person/day)
Personal expenses, souvenirs, tips
* Travel Insurance
* Other optional insurance
* Any applicable motorcycle model surcharges
* Flights & stopovers* Flights, additional accommodation & stopovers can all be arranged by Orange & Black
* Specialist Travel insurance for motorcyclists is available through: www.bikerstravelinsurance.co.ukOur Accommodation
Chicago, Embassy Suites Rosemont
Milwaukee, Hyatt Regency
Bloomington-Normal, Hampton Inn & Suites
St. Louis, Hyatt Regency St. Louis at the Arch
Springfield, Bass Pro Shops Angler’s Lodge
Tulsa, Hilton Garden Inn Tulsa Midtown
Weatherford, Best Western Plus
Amarillo, Big Texan Motel
Santa Fe, Inn of the Governors
Gallup, El Rancho Hotel
Flagstaff, Motel DuBeau Travelers Inn
Williams, Comfort Inn Near Grand Canyon
Needles, Best Western Colorado River Inn
Victorville, Hilton Garden Inn
Los Angeles, Sonesta LAXOur Motorcycles
For our selection of motorcycles please see our USA Motorcycle Rentals page.