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48-110°F
9-43°C

Route 66 Silver Jubilee Special Nostalgia Guided Motorcycle Tour

We’d love you to celebrate our Silver Jubilee with us in style, and what better way than on our new Route 66 tour! It’s 20 years since our customers first rode with us on our Route 66 Original tour and it’s remained our flagship tour to this day. Now we’ve put all of our experiences together to come up with a brand new Route 66 itinerary for you – a retro twist on our guided tour of the ‘mother road’. We’ve gone to great lengths to make this a unique and amazing experience.

Staying in independently owned and run historic hotels, nearly always in small towns, visiting less touristy locations and attractions and really getting under the skin of Route 66, this is truly going to be a unique ride.
Even if you’ve ridden Route 66 already, you won’t believe how much more you will see of the Mother Road on our Route 66 Silver Jubilee Tour. We’ve added a day to our Original tour itinerary, and this brings a very different rhythm and feel, and more time to meet people and soak in the history. We have just 15 Harley-Davidson motorcycles available……

Total Mileage c. 2700

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  • Grand Canyon

    Grand Canyon
  • Chicago - Route 66 start , Art institute, the blues!

    Chicago - Route 66 start , Art institute, the blues!
  • Topanga Canyon

    Topanga Canyon
  • Santa Fe, New Mexico - oldest state capital in USA

    Santa Fe, New Mexico - oldest state capital in USA
  • Less touristy attractions

    Less touristy attractions
  • Angeles Crest Highway

    Angeles Crest Highway
  • Staying in historic motels and inns

    Staying in historic motels and inns
  • Al Fresco BBQs

    Al Fresco BBQs
  • Santa Monica Pier - the end of the road

    Santa Monica Pier - the end of the road
  • Oatman Highway

    Oatman Highway
  • Meeting our good friends along the way

    Meeting our good friends along the way
Expand all
Collapse all
Day 1 Hello Chicago! Arrive
Day 1 Hello Chicago!

Welcome to Chicago! On arrival at the airport make your way to our tour hotel. Once at the hotel you can either relax in the hotel or you could visit downtown Chicago, for numerous sightseeing, dining and shopping opportunities.
Just be sure to be back in time to meet your tour guides at the hospitality desk, get signed in and enjoy the complimentary welcome dinner this evening. It all begins now!

If you want more time to explore downtown, why not stay an extra night or two – we can arrange everything for you!

Day 2 Chicago – Dwight, IL - 105 miles, 4 hrs
Day 2 Chicago – Dwight, IL

After breakfast, we load up the support van and off we go. We pick up our motorcycles at our Chicago dealership, and then the adventure begins.

When on the road some of the many highlights of the day will include The Route 66 start point, Blues Brothers, Dick’s Towing, Gemini Giant. And that’s all before lunch where we will stop at the Polk-a-Dot drive in. More exploring takes place this afternoon with the final stop for the day being Dinner at the Cherry Red Roasters BBQ

Day 3 Dwight – Carlinville, IL - 170 miles, 4-1/2 hrs
Day 3 Dwight – Carlinville, IL

We ride on through small town America today. Our stops will include The Pontiac Museum and an unusual farm - Funks Grove Maple Sirup - before we lunch at the Road Ranger Café. And before dinner, we will visit Brick road and Carlinville brick-lined square and impressive domed courthouse.

Day 4 Carlinville – Lebanon, MO - 230 miles, 5 hrs
Day 4 Carlinville – Lebanon, MO

Our first stop of the day will be the world famous Chain of Rocks Bridge. Followed by stops at Route 66 State Park,
Ted Drewes frozen custard shop and Bourbeuse Harley Davidson. Lunch will be at Missouri Hick BBQ. Then its on to the Devils Elbow and the day will conclude with good old Pizza by the pool – Orange & Black Style !

Day 5 Lebanon – Claremore, OK - 225 miles, 5 hrs
Day 5 Lebanon – Claremore, OK

We will start the day with breakfast at Elm Street Eatery, then it son to Gay Parita gas station, Boots Court and Cars on 66.
Lunch will be at Waylan’s Ku Ku Burger. The afternoon will include stops at 9 Ft road, Vintage car museum and Will Rogers Inn. Dinner will be at Eggberts.

Day 6 Claremore – Shamrock, TX - 320 miles, 6 hrs
Day 6 Claremore – Shamrock, TX

From Claremore we head to Warwick and the Route 66 Museum and then on to Lake Overholser.

Lunch will be at the fantastic Sid’s Diner in El Reno before moving on to the Route 66 Museum in Clinton and the U Drop Inn. For Dinner it will be a trip to Big Vern’s Steakhouse for steak, American style !

Day 7 Shamrock – Tucumcari - 215 miles, 4 hrs
Day 7 Shamrock – Tucumcari

Breakfast this morning will be at the Route 66 iconic Big Texan steakhouse followed by a spray paint session at the Route 66 iconic, Cadillac Ranch. Ugly pies can be eaten at Mid Point Café and a photo or taken outside as we celebrate making it half way down Route 66. Then it’s on to Glenrio Ghost town stop before finishing in Tucumcari with an authentic BBQ experience.

Day 8 Tucumcari – Santa Fe, NM - 190 miles, 3-1/2 hrs
Day 8 Tucumcari – Santa Fe, NM

Leaving Tucumcari we ride to Santa Fe, stopping for lunch at Johnny’s Mexican Kitchen before arriving into Santa Fe in late afternoon with plenty of time to wander the streets before dinner.

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 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 10 Santa Fe - Holbrook, AZ - 300 miles, 6 hrs
Day 10 Santa Fe - Holbrook, AZ

Leaving Santa Fe we head south and to the Town of Madrid.
Lunch will be at WOW Diner and then its on to Yellowhorse Trading Post, The Petrified Forest National Park and Painted Desert before ending the day in Holbrook, Arizona with a BBQ never to be forgotten.

Day 11 Holbrook – Williams, AZ - 130 miles, 2-1/2 hrs
Day 11 Holbrook – Williams, AZ

After leaving Holbrook, we head for Winslow and you can have your very own chance to “Stand on the Corner” for a photo opportunity not to be missed. With stops also at the Pine Breeze Motel and Lunch at Belmont HD, this will be one of those days you never forget.

Day 12 Williams - Seligman, AZ - 180 miles, 4 hrs
Day 12 Williams - Seligman, AZ

Start the day with an optional helicopter ride over and through the Grand Canyon. Followed by a picnic lunch on the rim of the canyon. Then it is back to Williams for the short ride to Seligman.

Day 13 Seligman – Needles, CA - 160 miles, 3-1/2 hrs
Day 13 Seligman – Needles, CA

We head off across the desert to Hackberry and then Kingman, the self-styled ‘Capital of Route 66’. Then comes what Americans like to call the ‘curviest’ part of the Route, the Oatman Highway, a twisting ride over the Black Mountains. Oatman is one of the few remaining old west gold mining towns and don't be surprised by its burros roaming the main street, left behind when the miners abandoned the mines. We overnight in California at Needles on the edge of the Mojave desert.

Day 14 Needles – Wrightwood, CA - 235 miles, 5 hrs
Day 14 Needles – Wrightwood, CA

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 Roy’s Motel and Café. We continue to our lunch stop in Barstow and then on to see 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 before our last day of riding tomorrow.

Day 15 Wrightwood - Santa Monica - 110 miles, 5 hrs
Day 15 Wrightwood - Santa Monica

The big adventure comes to an end today with our ride to Los Angeles. It’s a final twisting mountain ride on the beautiful Angeles Crest Highway. We'll stop for coffee at Newcomb's Ranch and then ride on through Topanga Canyon. The end of the Mother Road, Santa Monica Pier, is the perfect finale. 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 final 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 Dinner.

Day 16 Goodbye Los Angeles - Depart
Day 16 Goodbye Los Angeles

Sadly it’s time to pack our bags and head home, filled with the experiences and memories of this nostalgic ride down the 'mother' road. We hope to see you back for another great tour. This is end of the road - for now!

  • Our Tour Price Includes
    • The best motorcycle guides in the business
    • Harley-Davidson® rental motorcycle (current model, under 18k miles, factory warranty)
    • 6-12 riders per tour (max 15)
    • Fully equipped support van
    • Spare motorcycle
    • Free WiFi throughout the tour
    • The best biking roads and personally selected stops
    • Hand picked accommodation in 2-4* hotels (See Our Accommodation section)
    • First Aid/Responder kit
    • Guide-to-guide intercoms
    • Deputy guide, who can also ride
    • Water and ice on tour
    • Fuel
    • Welcome & Farewell dinners, some breakfasts
    • Basic 3rd party liability cover
    • All taxes, compulsory charges and 1-way fees
    • Emergency assistance
    • Park and any other entrance fees
    • Conference, rally and other event surcharges
    • Parking fees
    • Detailed personal tourbook & tour souvenirs
    • Orange & Black USA Travel Guide
    • £ price guarantee (no exchange rate worries)
    • Low £250 booking deposit
    • ATOL protection
    • Peace of mind from our Travel Trust Association membership
    • Our unrivalled experience and knowledge
  • 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 (VIP) & SLI motorcycle insurances Excursions/activities Pre and post tour accommodation UK airport hotels and parking Trike Highway pegs & rider backrest, FREE Other makes and models of motorcycle Model guarantee Hotel/rental location transfers Helmets & riding gear (we recommend you bring your own) Car/van hire Custom/private tours
  • Our Tour Price Does Not Include
    • £50 discount for previous customers and HOG members
    • 5% group discount for 4 or more motorcycles
    • Meals except where specified (allow c. £30-40/person/day)
    • Personal expenses, souvenirs, tips

Harley-Davidson® Motorcycles

Electra Glide Ultra®

  • Grand Touring class motorcycle
  • Passenger seat
  • Passenger backrest
  • Top storage case
  • 6 gallon capacity / 42 MPG
  • 12 volt power port
  • Surcharge applies
  • Suitable for: rider + passenger
  • 27.4 inch seat height
  • Saddle bags
  • Windshield
  • MP3, radio, Bluetooth, USB
  • GPS navigation

Street Glide Grand Touring

  • Grand Touring class motorcycle
  • Passenger seat
  • Passenger backrest
  • Top storage case
  • 6 gallon capacity / 42 MPG
  • 12 volt power port
  • Suitable for: rider + passenger
  • 26.1 inch seat height
  • Saddle bags
  • Windshield
  • MP3, radio, Bluetooth, USB
  • GPS navigation

Street Glide®

  • Touring class motorcycle
  • Passenger seat
  • Passenger backrest
  • Windshield
  • MP3, radio, Bluetooth
  • GPS navigation
  • Suitable for: rider + passenger
  • 26.1 inch seat height
  • Saddle bags
  • 6 gallon capacity / 42 MPG
  • 12 volt power port

Road Glide®

  • Touring class motorcycle
  • Passenger seat
  • Passenger backrest
  • Windshield
  • MP3, radio, Bluetooth,
  • GPS navigation
  • Suitable for: rider + passenger
  • 25.9 inch seat height
  • Saddle bags
  • 6 gallon capacity / 42 MPG
  • 12 volt power port

Road King®

  • Classic class motorcycle
  • Passenger seat
  • Passenger backrest
  • Windshield
  • Suitable for: rider + passenger
  • 26.3 inch seat height
  • Saddle bags
  • 6 gallon capacity / 42 MPG

Heritage Softail classic®

  • Classic class motorcycle
  • Passenger seat
  • Passenger backrest
  • Windshield
  • Suitable for: rider + passenger
  • 25.5 inch seat height
  • Saddle bags
  • 5 gallon capacity / 42 MPG

Low Rider®

  • Street class motorcycle
  • Passenger seat
  • Passenger backrest
  • 4.7 gallon capacity / 42 MPG
  • Suitable for: solo rider
  • 25.4 inch seat height
  • Saddle bags

Harley® Sportster XL1200 custom

  • Street class motorcycle
  • Passenger seat
  • Saddle bags
  • Suitable for: solo rider
  • 25.7 inch seat height
  • 3.3 gallon capacity / 42 MPG

Harley® Tri Glide Ultra

  • 3-Wheel motorcycle
  • Passenger seat
  • Passenger backrest
  • 6 gallon capacity / 42 MPG
  • MP3, radio, Bluetooth, USB
  • GPS navigation
  • Suitable for: rider + passenger
  • 27.1 inch seat height
  • Saddle bags
  • Windshield
  • 12 volt power port
  • Surcharge applies

Yamaha Bolt

  • 952CC Street class motorcycle
  • Suitable for: solo rider
  • Available in Las Vegas, Los Angeles, San Francisco and Seattle only

Yamaha MT07

  • 700CC Street class motorcycle
  • Suitable for: solo rider
  • Available in Las Vegas, Los Angeles, San Francisco and Seattle only.

Yamaha Tracer 900GT

  • Sport Touring class motorcycle
  • Suitable for: rider + passenger
  • 900CC model available in Las Vegas, Los Angeles, San Francisco & Seattle only

Yamaha Super Tenere 700

  • 700CC Adventure Touring class motorcycle
  • Suitable for: rider + passenger
  • Available in Las Vegas, Los Angeles, San Francisco and Seattle only

Yamaha Super Tenere 1200

  • 1200CC Adventure Touring class motorcycle
  • Suitable for: rider + passenger
  • Available in Las Vegas, Los Angeles, San Francisco and Seattle only

Royal Enfield Continental GT650

  • Suitable for: solo rider
  • Available in Los Angeles, San Francisco and Seattle

Royal Enfield Interceptor 650

  • Suitable for: solo rider
  • Available in Los Angeles, San Francisco and Seattle

Royal Enfield Himalayan

  • Suitable for: solo rider
  • Available in Los Angeles, San Francisco and Seattle

BMW 1200RT

  • Sport Touring class motorcycle
  • Suitable for: rider + passenger

BMW R1200GS

  • Adventure Touring class motorcycle
  • Suitable for: rider + passenger

Honda Goldwing

  • Sport Touring class motorcycle
  • Suitable for: rider + passenger

Bring Your Own

You can save money on your trip if you bring your own bike. However you need to arrange transport of it.

Bring Your Own

  • Save on hire costs by bringing your own bike
  • However, you need to arrange transport of your bike to the tour start point

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